308: LILY ALLEN DEEP DIVE

Summary

Pop Apologists – Episode 308: Lily Allen Deep Dive

Released: December 2, 2025
A podcast by two sisters (Lauren & Chandler) who care about celebrities as much as their family.

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Main Theme / Purpose

This episode is a comprehensive deep dive into the life, career, personal struggles, and latest artistic achievements of British pop star Lily Allen. The sisters, Lauren and Chandler, offer a detailed walk-through of Allen’s upbringing, her rise to stardom, her relationships, public controversies, and the creative renaissance exemplified by her latest album, “West End Girl.” Largely guided by Lauren’s immersive reading of Lily’s memoir, the episode promises empathy and context for a figure often reduced to tabloid headlines.

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Key Discussion Points & Insights

1. Why Lily Allen, Why Now?

[01:44]

• A listener-driven return to the podcast’s “deep dive” format, focusing on the relevance of Lily Allen’s current renaissance.
• Chandler: “We are truly living in a Lily Allen renaissance right now. We are with West End girl.”

2. Lily Allen’s Early Life & Family Turmoil

[03:46–08:05]

• Born in London on May 2, 1985 (Lauren: “My wedding anniversary, everybody”)—daughter of actor Keith Allen and producer Allison Owen.
• Early years marked by financial strain despite industry ties.
• Parental divorce and a fraught relationship with her father:

  “I have probably spent more time walking my dogs than I have with my dad my entire life.” (Lauren, [05:21])

• Notable stories:
  • Her father missing her festival headline show, despite being at the same event ([06:04]).
  • Keith Allen’s philandering, multiple children from different relationships.
• Siblings: closest to Sarah and Alfie, the latter known for his role on Game of Thrones.

3. Troubled Adolescence and Finding Music

[08:29–13:37]

• Attended 13 schools, often expelled for misbehavior.
• Discovered musically after a teacher overheard her sing Oasis’s “Wonderwall.”
• Dropped out at 15—later regretted not completing her education:

  “I don’t even have one GCSE...and I am ashamed of it.” (Lauren, paraphrasing Lily, [09:03])

• Runaway years in Ibiza:
  • Worked in a record shop, briefly dealt ecstasy, lived in hostels.
  • Met George Lamb (who would become her manager), who looked out for her rather than exploit her:

    “It was one of the first times a man had done something nice for me without any sexual agenda.” (Lily Allen memoir excerpt, [12:04])

4. The Nepo Baby Discussion: Privilege and Pain

[13:56–16:37]

• Early record deal via her dad’s connections led to nothing.
• Allen’s own take on being labeled a “Nepo baby”:
  • Acknowledges privilege but stresses that class and family trauma complicate the narrative:

    “The idea that they handed things to me on a plate is sort of complicated. But whatever, I’m just happy and I’m very grateful.” (Lily Allen memoir, [15:40])

  • On X/Twitter:

    “Nepo babies are starved of these basic things in childhood, as their parents are probably narcissistic...it can be hard to see one’s own privilege when you’re still processing childhood trauma.”

5. Music Breakthrough: DIY Stardom and Signature Lyrics

[19:16–25:45]

• Early label deal (for 5 albums!) but little support.
• Took to MySpace, gaining 74,000 fans and industry buzz.
• Released “Smile” in 2006:
  • Became a “petty breakup anthem,” shot to #1 UK charts ([21:44]).
  • Debut album “Alright, Still” mixed ska, reggae, hip hop, and pop; double platinum sales ([22:18], [22:47]).
• Song “Alfie” about her stoner brother brought good-natured family ribbing.
• “LDN” painted London’s glamour with a gritty underbelly—Allen praised for authenticity:

  “There was no distance between her music and her personality.” (Chandler, [23:32])

6. Peak Fame, Critics, & Female Power Era

[25:45–29:30]

• Surged as a tabloid target—unfiltered interviews and “party girl” tropes dogged her.
• Second album “It’s Not Me, It’s You” (2009) shifted to electro-pop; produced the hit “The Fear,” a satirical take on fame and consumerism:

  “I’m a weapon of massive consumption and it’s not my fault, it’s how I’m programmed to function.”

• Won prestigious Ivor Novello songwriting awards—her proudest artistic moment.

7. Career Highs and Personal Lows: Stepping Back and Tragedy

[34:34–39:50]

• At 25, Allen stepped back from music, yearning for a “normal” life and children.
• Relationship with Sam Cooper, tragic stillbirth of their first child George, and traumatic aftermath:

  “It’s not something you get over.” (Lily Allen, via [38:00])

• Later two daughters born, with first (Ethel) struggling with severe medical issues.

8. Struggles with Motherhood & Loss of Identity

[39:16–43:40]

• Lily experienced postnatal (postpartum) depression, feeling unprepared and shocked at the realities of motherhood.

  “Neither of my parents were particularly good at parenting, so it wasn’t a skill set that I had.” (Lauren, paraphrasing Lily, [39:50])

• Chronic money woes and avoidance of adult responsibilities (like years of unpaid tickets).

9. Comeback, Industry Setbacks & Public Reactions

[43:44–48:19]

• Returned with “Somewhere Only We Know” cover for John Lewis adverts ([43:44]).
• Third album “Sheezus” (2014) struggled to replicate earlier success; less connected to its artwork and image.
• Honest about creative burnout and managing motherhood:

  “She was just so busy being a mom and trying to also release new music.” (Lauren, [47:47])

10. Self-Destruction, Affairs, & Support Systems

[48:19–55:02]

• Touring “Sheezus,” Lily spiraled into self-mediated substance use and infidelity, including sex with female sex workers (which she rationalized as "not cheating").
• Notably, an incident involving Orlando Bloom at a party—passed out and later found herself being looked after by Kate Hudson and Chris Martin. Chris intervened, urging her to seek help and inviting her for a supportive lunch with him and Gwyneth Paltrow:

  “[Chris Martin] was really...he kind of says, you know, clearly things are not right and you’re not well.” (Lauren, [50:56])

• Divorce from Sam Cooper followed (after being compelled to disclose every detail of her affairs).

11. Sexual Assault, Stalking, and Further Trauma

[55:02–60:03]

• Endured sexual assault by a music industry executive—documented it legally but did not go public immediately.
• Terrifying series of stalking incidents, including home invasion by Alex Gray in 2015:

  “He began harassing her in 2008, and he ultimately broke into her London house in 2015 while she and her children were sleeping.” (Chandler, [56:16]) “Because the world would be a better place without her…and that’s what I’m here to do.” (Alex Gray at bail hearing, via Lily Allen, [59:16])

12. Art from Adversity: “No Shame” and Radical Honesty

[60:03–61:08]

• Channeled trauma and heartbreak into 2018’s “No Shame,” acclaimed for vulnerability but modest sales.
• Released memoir “My Thoughts Exactly” tackling infidelity, substance abuse, depression, and an affair with Liam Gallagher.

“Basically, I sort of figured out…that actually if you just, like, tell everyone everything there is to know and then they can’t come after you.” (Lily Allen memoir excerpt, [62:42])

13. Sobriety, Parenting Wins, and a New Love

[62:58–65:09]

• Achieved sobriety; describes herself as a better and more present parent:

  “My relationship with my kids specifically is much better since I got sober.” (Lily Allen, [63:40])

• Matched with actor David Harbour on Raya (2019); whirlwind romance and Las Vegas wedding in 2020.

14. West End Girl: Renaissance & Recent Heartbreak

[65:09–71:35]

• 2021: Star turn on London’s West End, earning critical raves. Launched “Miss Me” podcast.
• Marriage to Harbour falters—2023 separation rumors, confirmed in early 2025.
• Lily copes via songwriting; releases “West End Girl” (2024), an album lauded for brutal candor and artistic depth:

  “A gobsmacking autopsy on a marital betrayal that is cathartic and brutally candid, but also stylistically varied with melodies and sparkle.” (The Guardian, [70:23]) “As long as I can just say what happened to me, I can leave with my dignity.” (Lauren, paraphrasing Lily, [71:09])

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Notable Quotes & Memorable Moments

• On Class, Nepotism, and Trauma:

  “We don’t care about money or proximity to power. Yet many of the Nepo babies are starved of these basic things in childhood, as their parents are probably narcissistic.” (Lily Allen, via Chandler, [15:40])

• On Early Industry Experiences:

  “I hope you didn’t mind, I went through your phone, I called your mum...It was one of the first times a man had done something nice for me without any sexual agenda.” (Memoir excerpt, [12:04])

• On Her Song “The Fear”:

  “It works so well because she implicates herself in the worst aspects of the fame industry...I’m such a hypocrite, but that’s why I love that song.” (Lauren/Chandler, [26:54])

• On Infidelity and Saving Herself:

  “Maybe I did want to get caught. Maybe I wanted Sam to rescue me.” (Lily Allen, via Chandler, [54:21])

• On Sobriety’s Rewards:

  “She’s naming her emotions and she’s asking me for help. My relationship with my kids specifically is much better since I got sober.” (Lily Allen, [63:40])

• On Radical Confession:

  “If you just, like, tell everyone everything, then they can’t come after you and they can’t follow you anywhere.” (Lily Allen, [62:42])

• On “West End Girl” and Artistic Legacy:

  “In its own way, West End Girl is the culmination of everything Lily Allen represents: unfiltered honesty, dark humor, and turning these chaotic parts of life into art.” (Chandler, [70:23])

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Timestamps for Key Segments

• [01:44] – Why this Lily Allen deep dive?
• [03:46] – Lily's family background and early childhood
• [05:21] – Strained relationship with her father
• [11:19–12:45] – Lily’s Ibiza runaway/early manager story (Memoir excerpt)
• [13:56] – Nepo baby conversation and Lily’s nuanced view
• [19:16] – Music industry struggles; breakthrough via MySpace; “Smile”
• [22:47] – “Alright, Still” and songs about family
• [24:20] – “LDN” and songwriting style
• [26:49–28:38] – “The Fear,” awards, and industry satire
• [34:34] – Retreat from fame, marriage, and catastrophic loss
• [39:50] – Postnatal depression and “fairytale” motherhood
• [43:44] – Musical comeback and struggles with industry/identity
• [48:19–51:05] – Downward spiral; Chris Martin’s intervention (Memoir excerpt)
• [55:02–59:15] – Sexual assault by music exec and deeply frightening stalking ordeal
• [60:03] – “No Shame” album and memoir
• [62:42] – On public confession as self-defense
• [63:40] – Sobriety and parenting
• [65:09] – Meeting and marrying David Harbour
• [67:29] – Divorce and “West End Girl” inspiration
• [70:23] – “West End Girl” as confessional peak

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Overall Tone & Takeaways

Balancing wry humor, empathy, and forthrightness, Lauren and Chandler deliver a complex, humanizing portrait of Lily Allen. They move beyond tabloid caricatures to examine her childhood trauma, the double-edged sword of privilege, the growing pains of musical stardom, and her capacity for self-reinvention through self-exposure. The episode ends with appreciation for Allen’s latest work and hopes for her healing and future happiness.

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Recommendation

If you’ve ever reduced Lily Allen to a punchline or a pop culture footnote, this episode is a must-listen (or must-read), painting a portrait of a resilient, messy, and ultimately admirable artist. For Allen newcomers and longtime fans alike, it’s a reminder that the chaos of celebrity and personal life can still inspire genuine artistry and growth.

Required listening: Allen’s “West End Girl,” “The Fear,” and “Smile.”
Required reading: Her memoir, My Thoughts Exactly.

Transcript

[Lauren]

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[Chandler]

And it's been a minute since we've done a deep dive on the show. And people say. They say pop apologists bring back the deep dives. And you know what? We are listening to your requests. And who better to deep dive than Lily Allen? We are truly living in a Lily Allen renaissance right now. We are with West End girl.

[Lauren]

It's true. It's true.

[Chandler]

I feel like for a lot of millennial girlies, Lily Allen was. Her music was super popular a long time ago, but she kind of took a step back for a while. And so we might want to kind of re familiarize ourselves with who exactly this woman is.

[Lauren]

Yeah, she's traveled a long road at times a hard road. I would just like to come before you and tell you that I did spend the entire day today listening to her memoir.

[Chandler]

Okay.

[Lauren]

So I am completely steeped in all of her, you know, all of her tales, her life story, everything. Um, and I feel like there's just a. A lot more to her story and to her upbringing than I obviously knew about. And I think for most people, like, they won't know everything about her.

[Chandler]

Yeah. Well, I'm proud of you for two reasons. One, you've really done the work, so thank you. You're showing up today very prepared. Two, you pronounced it memoir and not memoir, which is we haven't.

[Lauren]

We've gotten in trouble for the way we've said.

[Chandler]

Always say memoir like you memoir. It's always the most theatrical pronunciation of memoir.

[Lauren]

It's a lot sexier sounding than biography autobiography.

[Chandler]

It's like when someone says fiance instead of fiance.

[Lauren]

Excuse me for trying to add some audio flair to, you know, to our audio only job.

[Chandler]

No, we appreciate it. But without further ado, should we get into the life and loves of Lily Allen?

[Lauren]

Yeah, I think that once again, it's a. It's a hard road she's been on. And maybe this is because I've, I've read the book, but we're obviously, we're so caught up in the David Harbour of it all, but there was just a lot of other crazy shit that happened even before David Harbour. So, yeah, let's get into it. Let's, you know, I don't want to give anything away too soon.

[Chandler]

Okay. Well, Lily Allen was born in London on May 2, 1985.

[Lauren]

My wedding anniversary, everybody.

[Chandler]

Oh, my gosh. That is so germane. Thank you.

[Lauren]

I can't see that date without saying it. Also the anniversary of when Osama bin Laden was assassinated.

[Chandler]

I thought you were gonna have some anniversary between you and Ben. And I was just thinking, God help us all.

[Lauren]

Anyways, an important date for a lot of reasons.

[Chandler]

Okay. Two huge moments in American history.

[Lauren]

My marriage.

[Chandler]

Marriage, UBL getting taken out. Oh, and Lily Allen being born. Yeah, May 2nd is huge. Well, 1985, so really none of this happened on the Same day, but May 2nd.

[Lauren]

Okay, let's move forward, please. Skip has the first sentence.

[Sponsor/Ad Voice]

Dear God.

[Chandler]

Into a show business family. So her father is the actor and comedian Keith Allen, and her mother, Allison Owen, is a movie producer. So Lily describes her childhood as very turbulent. Her father left when she was just four years old. And her early life was not one of wealth or luxury. It was financially strained. In her early years with Lily, her mother and her siblings actually living in government housing when she was a child. So Lily said, I lived in a council flat for the first nine years of my life eating spaghetti on toast. As her mother's career grew, the family's financial state became a lot more stable. So in spite of this early financial struggle, given that both of her parents were in the entertainment industry, she did have some privilege in terms of being able to be connected to the powers that be in the music industry or some powers that be.

[Lauren]

Yeah, I would say, you know, she's not a Nepo baby in the sense that she just had a silver spoon in her mouth her entire life and just, you know, was just. She's not readily a Richie Grange. Yeah, she's not Sophia Richie Grange, you know, whose clothing line is now available at Revolved, but she is. She definitely was well connected. She was well connected from the get go. So while now Lily has a good relationship with her mother, although it's had its struggles, she's continued to have a pretty strained relationship with her father. She said, my dad walked out on me when I was 4. My dad was at Latitude and English Music Festival when I headlined and didn't even come to see me. I probably spent more time walking my dogs than I have with my dad my entire life. I have a couple stories here from her book I want to share.

[Chandler]

Okay, Please do. But I just really want to, you know, double tap on this moment where she's headlining a musical music festival her dad is at, and he doesn't even come to see her.

[Lauren]

Yeah. So. Okay, well, I'll get to that story first. So her dad, like, comes to chat with her before she's about to go, like, headline. And she's. And he says, oh, I gotta go off and do other stuff. And she's like, aren't you gonna stay for my show? And he just, like, has some excuse for why he's not going to stay. And it was like, in that one moment, I think she just really realized how, like, the one person she wanted to, like, be proud of her and watch her perform, like, wasn't interested.

[Sponsor/Ad Voice]

So her.

[Lauren]

She says that she has one memory. She says, my, you know, my dad left when I was four. She's one memory of her parents together.

[Chandler]

Okay.

[Lauren]

And it is of her mom being in bed and there being a man in her bed.

[Chandler]

That's not her father.

[Lauren]

That is her father. That's her only memory of her parents being together.

[Chandler]

Wow.

[Lauren]

Which is pretty crazy. Her dad also was kind of a philanderer, actually. He was a philander. Not kind of.

[Chandler]

Yeah.

[Lauren]

In fact, There was, like, a time when. When her mom was, like, about to start on a big show. She had a big production job, and her dad said, hey, you know, I'll take the kids for. On a holiday for the week, and you can just focus on work and we'll get them out of your hair. And her mom was, like, so grateful and was like, that. That would be so great. Thank you. And Lily says that she. They get to this hotel, I think they were saying, somewhere, like, on the. Like, the coast of France in the south of France, and the woman staying at the hotel room next to them just happened to be somebody her dad worked with another woman, and that it was like they. They did one of those, like, oh, my gosh, so crazy. You're here, too. Well, let's hang out together. Well, you know, while we're both on holiday with whatever. And obviously they had actually planned the whole thing because they were having an affair. Wow. Isn't that crazy? And he ended up marrying her soon thereafter after they got a divorce.

[Chandler]

Oh, my gosh.

[Lauren]

Anyway, that marriage didn't last very long. She actually also says that her dad has maybe eight or nine kids across different women, too.

[Chandler]

Fantastic.

[Lauren]

Yeah.

[Chandler]

Anyway, okay, well, Keith Allen, not exactly on our Mount Rushmore of monogamy, but we must press forward.

[Lauren]

So she has an older sister, Sarah, and she has two younger siblings, Alfie and Rebecca. You might know Alfie from Game of Thrones. He plays Theon Greyjoy. Do you remember? You've watched Game of Thrones. I have not watched Game of Thrones. You should watch it.

[Sponsor/Ad Voice]

It's great.

[Lauren]

Anyway, she has more siblings, but I think she's the closest to Sarah and Alfie.

[Chandler]

Gotcha. So. So as a child, Lily felt lonely and often rebellious. She attended 13 different schools, and she was frequently expelled for misbehavior, like smoking and drinking. But at age 11, a teacher overheard her singing Oasis's Wonder Wonder Ball and was so impressed that she gave Lily voice lessons and a solo in the school's concert, where the formerly angry little girl moved the audience to tears. This encouragement ended up being a turning point for her, and she realized that music could give her a positive outlet and could have a really good effect on people, providing a source of valid foundation that she really craved.

[Lauren]

Yeah, she really bounced around a lot, and she ended up even dropping out at the age of 15. She says she regrets this going on. She says, I'm not educated. I left school when I was 15. I don't even have one GCSE. It's the standard Exam in British Education. Not one qualification, and I am ashamed of it. I really wanted to go into midwifery or obstetrics because that was something that really interested me. But I, but because I didn't have any diplomas or GCSEs or A levels, it seemed too difficult, too much. I was too lazy and actually too embarrassed. I, I thought I'd have to go and do my A levels with a bunch of 18 year olds and I was already in my mid-30s. I didn't want to do that. So schooling was just really tough the entire time. And she didn't really even end up finishing it.

[Chandler]

Yeah, she ends up going to Ibiza, actually, which sounds like a lot of fun.

[Lauren]

Another kind of schooling, another type of learning experience.

[Chandler]

Exactly. You know what they say, don't ever let school get in the way of your education. And she, she certainly got an education in Ibiza. She told her mom that she was on holiday with friends, but she ended up staying there alone, working at a record store and sometimes dealing ecstas pills to partygoers.

[Lauren]

Yeah, there are some crazy stories from this. Okay, so actually I think her mom was on vacation nearby, like in Greece maybe. But then she ended up like hopping a boat or plane to Ibiza. Okay, Ibiza. What do we, what do we decide to do on this podcast? We're going to call it Ibiza Podcast on this podcast, Ibiza. So she hopped a boat, shopped on a boat, hopped on a plane, got to Ibiza, got a job at a record store, was like staying in a hostel, but then got kicked out of the hostel because she wasn't paying her bills.

[Chandler]

Oh, wow.

[Lauren]

Yeah.

[Chandler]

And you know, you're down on your luck when you can't pay the hostel.

[Lauren]

And when you're 15 and dealing ecstasy.

[Chandler]

Also a sign things are going well.

[Lauren]

Yeah, I mean, just really quite extraordinary and extraordinary childhood and just, you know, meanwhile you and I are, you know, 15 and we're not even allowed to see PG13 movies.

[Chandler]

No.

[Lauren]

But what's interesting here is that she actually ends up meeting her first manager, George Lamb here and there's like a, a great story that actually I'm going to play from her memoir. I'm going to. Hold on. Okay, I'm going to play a little snippet here from her book where she talks about meeting her first manager, George Lamb, while she's in Ibiza, while she's on this crazy little, you know, journey, I should say, of selling ecstasy and being 15. Okay.

[Lily Allen (Memoir excerpts)]

I was booted out of my room at the Welsh hostel for not paying my bill. So my drama that night became where the am I going to sleep? The problem was solved when I ran into a DJ I knew, a bit called John Ulysses, who said I could stay on his sofa once he'd finished his set at a club called Esparadis. That night I took my suitcase to Esparadis and got talking to a guy called George. He told me he was working the season promoting the club space, and he rented his own place for the summer. He saw my suitcase and asked me where I was staying. I've been thrown out of my hostel, I told him, but it's okay because John Ulysses has offered me his sofa. I'm staying with him tonight. No, you're not. George said, not on your own. John Ulysses is a perv. Look, he continued, come back and stay with me. George was fit and quite a bit older than me. He was exactly my type. I assumed he was making a pass at me. I thought I was in. But George didn't come on to me. He took me back to his house and made up a bed for me on his sofa. When I woke up the next morning, he poured me a cup of coffee. I hope you don't mind, he said, but I went through your phone while you were asleep and I called your mum. I told her that I don't think you should be here anymore. I'm going to take you to the airport and put you on a plane back to London. And that's what he did. It was an amazing thing. It was one of the first times a man had done something nice for me without any sexual agenda. George was a life changer. I didn't know that then, and I didn't think about him much after that. But he held onto my number and nearly two years later, he rang me at exactly the moment I needed to hear from him.

[Lauren]

Okay.

[Chandler]

In a world full of Andrew Mountbatten Windsors, be a fucking George. I mean, that is a gorgeous tale.

[Lauren]

Isn't that crazy?

[Chandler]

It's so crazy because it's just not at all where you think this is going. No.

[Lauren]

And. And to be hon, honest, you know, it's maybe one of the very few positive tales about a male interaction in the book.

[Chandler]

Oh, interesting.

[Lauren]

Yeah. There's just, you know, a lot of tales about negative ones.

[Chandler]

Yeah.

[Lauren]

And, yeah, I just, I. I found that to be very endearing. And the fact that he was like, I hope you didn't mind, I went through your phone, I called your mom. I'm putting, you know, you're going getting on a plane back to London because she was 15.

[Chandler]

I mean, nine times out of 10, that situation would have gone the exact way she thought it was going to go.

[Lauren]

Yeah, so. So she was, like, mentally prepared for that.

[Chandler]

I feel fortified by hearing that, too. Thank you, Chandler.

[Lauren]

Yeah, I thought that was. I thought that was a great story. So anyway, they end up working together later on, which we'll get to.

[Chandler]

Yeah, okay. Well, so in 2002, when she's 16, Lily's dad does use his industry contacts to secure her an initial record deal with London slash Warner Records. But nothing comes of this deal, and it ends without her even releasing any music.

[Lauren]

Yeah, I think we're going to get.

[Chandler]

Into kind of her.

[Lauren]

Her whole perspective on the Nepo baby conversation surrounding her. Because while her dad's connections did help her in some ways, they also didn't help her. I mean, record labels weren't necessarily eager to sign her because she had a reputation of being, like, a party girl and being. Being involved in the hard partying scene. And so anyway, I think that, like, I. I actually find her comments about being an EPO baby to be quite interesting. And I. And I think they, like, shed light on, you know, why it's actually not always a good thing.

[Chandler]

Well, yeah. So let's listen to her talk about being an EPA baby, essentially. And one thing I want to say is it would be very interesting to have such a strained relationship with your father who is. Made you a Nepo baby or has made you a Nepo baby. And also to have grown up very financially insecure and then have to carry the Nepa baby title.

[Lauren]

Yeah, yeah. It's like all of the downsides. Right. And barely any upsides.

[Lily Allen (Memoir excerpts)]

I mean, I have sort of complicated feelings about it, mainly because of the complicated relationship I have with my parents. So I think that, you know, obviously I know that I've been born into an incredibly privileged situation, and I have no problem or qualms with accepting that and the opportunities that have been afforded to me. But I think that that's more of the class that I was born into. Yeah. Where, you know, where I went to school and the connections that I was able to forge with people as a result of that. There are people in my family that I don't really have relationships with. So the idea that they handed things to me on a plate is sort of complicated. But whatever, I'm just happy and I'm very grateful.

[Chandler]

So she's also given other quotes about essentially this Nepo baby moniker she said on X in childhood. We crave stability and love nurturing. We don't care about money or proximity to power. Yet many of the Nepo babies are starved of these basic things in childhood, as their parents are probably narcissistic. And it can be hard to see one's own privilege when you're still processing childhood trauma. And a lot of these kids haven't figured that out yet, she says.

[Lauren]

She goes on in another tweet and says, I promise you, I'm not rooting for an industry full of people that had childhoods that look like mine. I just really think that we can't get to a real solution without identifying the real problem. As fun as it is to laugh at the kids of famous people, Nepo babies have feelings.

[Chandler]

Yeah. I mean, it's, it is so interesting. And that's something I really haven't considered. The idea that if you're the son or daughter of someone famous, there probably is a high degree of chance that you. That they are narcissists.

[Lauren]

Yeah. And that you were starved of some pretty basic things that you should have, you know, got as a child.

[Chandler]

Absolutely. Another tweet she says the Nepa babies y' all should be worrying about are the ones working for legal firms, the ones working for banks and working in politics, and we're talking about real world consequences and robbing people of opportunity. That's none of. But that's none of my business. But back to the music.

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[Lauren]

So in 2004, her manager introduced her to Future cut and she began to write songs. And she received a small record deal in 2005 with a 25,000pound budget to record an album. And this was kind of crazy because this first record deal that she actually gets, it's, it's for five albums. She is like contracted to do five albums with them. And I thought that, you know, I think that now, now knowing more about what we know about like Taylor Swift and you know, just like the, the music label, you know, side of the industry.

[Chandler]

Yeah, we're all an expert on music contracts.

[Lauren]

I know I am. I know I am. I just think that that's like, that's, it's pretty insane to be like, okay, I'm, you know, it's, I think you probably don't know what you're getting yourself into when you sign up to do five albums with one record. Oh, I think that's one label. I mean that's probably what they do with these early stars, right?

[Chandler]

They just want to lock them in for as long as possible because they're going to catapult them. The last thing they want to do is, like, do all this marketing and then they leave. But they obviously generally sign really bad deals when they're so young and powerless.

[Lauren]

Yeah. So the label execs did not give her much time and attention. They focused on the larger acts like Coldplay. And without a lot of guidance from her label, she actually turned to MySpace and was, like, using that to get her name out. You know, there wasn't Instagram or Snapchat or TikTok and. And even Facebook and YouTube were still, like, in their infancy. So MySpace was really where she was uploading demo tracks that she was working on. And word spread like wildfire. And by early 2006, tens of thousands of people were streaming her songs. The lyrics were witty, about everyday life, and she had 74,000 friends on MySpace, which was huge at the time. And then that buzz online led to the mainstream media paying attention. And so, you know, in 2006, the observer profiled her as an unsigned sensation. And by May of that same year, the music industry finally gave her creative control to finish her first record, which she did with producers like Mark Ronson and Greg Kirsten. And to just add some more context here, from my reading of her book, I think that the record label was just not really caring a lot about getting her album made. They signed her, but there was not a lot of, you know, mentorship that they were providing for her to, like, work with other producers or, you know, other music people to help get her, you know, complete record made. Yeah, they just did not pay her attention until there was other buzz from outside sources. And then they were like, okay, well, now we'll set you up with this person. I think it was, like, this famous producer or whatever from la, and, like, well, he can now work with you to, like, finish your record.

[Chandler]

Interesting.

[Lauren]

So her official debut single, Smile, hit the airwaves in the summer of 2006, and this was her first big hit. In Smile, which I'm sure everyone has heard, she sings about getting revenge on a cheating ex boyfriend and watching you cry with a smile. It became the Petty breakup anthem, you know, for all of the women in the UK and the us I'll say all over the world. Listeners loved Lily's songwriting style, and By July of 2006, it hit number one on the UK charts, eventually going double platinum. And she became one of the first artists to have their MySpace fan base really translate into real world sales.

[Chandler]

Yeah, yeah. And her debut album, all right, still arrived that month and was Both a critical and commercial success, entering the UK charts at number two and ultimately selling over 2.6 million copies.

[Lauren]

Okay. Another song off this album is called Alfie and it's about her brother. I think this is just kind of interesting to note because her brother really does not like the fact that the song exists. It's all about his laziness and constant weed smoking. And I think he still gets asked about it, like in interviews.

[Chandler]

So, so funny.

[Lauren]

He can't be bothered cause he's higher.

[Chandler]

Overall. The critics loved all right still for its mixture of ska, reggae, hip hop and pop influences. And her lyrics that were so full of her personality. So much so that the Guardian reported that there was no distance between her music and her personality. On songs like ldn, Lily paints an observational picture of London. The city looks like sunny and vibrant. Lyrics like sun is in the sky oh why, oh why would I want to be anywhere else? But in each verse, she reveals the gritty realities, muggings and homelessness lurking beneath London's surface.

[Lily Allen (Memoir excerpts)]

It doesn't get me down and I feel okay Cuz the sights that I'm seeing are priceless Everything seems to look.

[Lauren]

As it should But I wonder what.

[Lily Allen (Memoir excerpts)]

Goes on behind doors I feel.

[Lauren]

By 2007, she was not performing only on big stages, but she was becoming really a staple of tabloid headlines. And we know how the British press can be unrelenting. And they certainly had their way with Lily. So she would also give these kind of unfiltered interviews and she would speak her mind rather than any type of, you know, sanitized PR sound bites. She said, you know, at one point, I can be mouthy, but I'm a nice person. In the book, she talks about how she had to learn that you can't get drunk with journalists and that, you know, you think at one point she was. This journalist was with her and she thought he was kind of flirting with her and she thought they were just like bantering on and on. And then the next day, like the headline said otherwise, you know, just totally painted her out to be. I think like it was some big crazy headline of how much she loved cocaine. Yeah. And I think she like made a joke about cocaine. But she did love cocaine, I will say. But anyway, she just had to like learn some media hard lesson. Yeah. You know, and she said, I'm not in this business to be in the tabloids. I'm in it to make good music. Lily told The Guardian in 2006. And she was right behind all the tabloid photos. She was Connecting with people. One review from Pitchfork said. Not only does Alan deliver on the musical promise hinted at in her MySpace demos, she also acquits herself as a genuine personality with wit and attitude. Despair. But don't take it from me, you know how to google. She was always her best PR person anyway.

[Chandler]

The album success proved that beneath this party girl headline and fixture was really a genuine songwriting talent. One reviewer noted, it's all very well being in the papers, but if your music's rubbish, people won't buy it. The reason Alan's album has sold well is that it's stonkingly good. Lily's ability to turn her life into relatable pop songs set her apart from the formulaic pop stars of the time.

[Lauren]

By 2008, Lily was enjoying all this commercial success during a time the UK media referred to as the year of the Women in British music, alongside other artists like Adele, Duffy, Amy Winehouse and Leona Lewis, to name a few. So in 2009 she released her second album, It's not me, it's you. Her sound really evolved there from heavier ska to electro pop. And this is where she releases the Fear, which was her most successful song, I think we could say, or one of her most successful songs, if not the most successful. And it pokes fun at consumerism and celebrity culture, you know, from the inside of celebrity culture, from the inside of that world.

[Chandler]

Yeah.

[Lauren]

I saw an interview with her recently where she talked about how this is the song that she's the most proud of writing.

[Chandler]

Yeah. And critics basically agree that this is her best song. So in the Fear she contrasts dreamy melodies with lyrics like I'm a weapon of massive consumption and it's not my fault, it's how I'm program to function. Pointing a finger at both herself and the Fame machine. The songs loved by critics and fans for its self awareness. And the Guardian called the Fear one of her best songs yet, describing how it works so well because she implicates herself in the worst aspects of the fame industry. And Lily agrees with this review since she said I'm such a hypocrite. But that's why I love that song. It's so ironic and contradictory.

[Lauren]

I don't know how. One more thing about the Fear. So she won three evor Novella awards for this song and in the book she talks about how this is like the award that she was the most like overjoyed to get because this is like a. A musicians award. It is not about the industry or about the. The money power players in you know, in it, which is, which I think like a lot of these award ceremonies are kind of like pay to play or whatever. It's just like, it's more about the politics versus like the actual talent, you know, I dare say. And the panel of judges is like all songwriters and it's like, it, it's, it's a more impressive award to win. And so anyway, like, yeah, it's the UK's most prestigious music honors and it's dedicated specifically to songwriting and composition.

[Chandler]

It's so interesting because when we get up, when we like start approaching Oscar season, a lot of times you'll hear, oh, like, you know, ex actor Ben Affleck is campaigning for this Oscar. He's, you know, in the circuit, he's going to all of the, he's going out to all of the festivals and he's like really putting in the work to try to get this Oscar. And there I feel like so many of these awards really are the product of networking.

[Lauren]

Yeah, exactly.

[Chandler]

And the product of, you know, billboards. Yeah, exactly. So I think that is important to know, right?

[Lauren]

It's.

[Chandler]

This wasn't something that her, her label.

[Lauren]

Was able to get for her. One quick aside. I remember when I lived in la, all of the billboards around Grammy, whatever, Oscar season, you know, for your consideration. And I was always so confused by that. I'm like, did the judges drive by here? But it really is all about like kind of the most buzz worthy. Like it's about the campaigning.

[Chandler]

Yeah, absolutely. So it's not me, it's you. This album debuted at number one in the UK and reached number five on the US Billboard music charts, selling over 2 million copies, cementing her in music stardom. Other songs on the album displayed her signature blend of humor and honesty, which set her apart from other artists, as we've discussed. And this brings us to another seminal Lily Allen song and a song that I would say she, you know, is still played a lot, especially on TikTok today. And it's the song you. So in this song, it's a deceptively upbeat melody with a message directed at bigotry and conservative politics. It was initially written as a protest against President George W. Bush. The working title was Guess who Batman, an anagram of gwb. But Lily later noted it could be aimed at anyone who deserves the middle finger. The song has had lasting appeal, going viral again in recent years as a soundtrack to anti Trump memes. So while Chandler was penning, you know, letters in support of George W. Bush and his decision to go to war. Yes, we do have conservative parents who brainwashed Chandler when she was 7 years old or 6. And so she wrote a very funny. For anyone who has not heard the story, she wrote a hilarious letter to George W. Bush when she was sick saying in like her, in her chicken scratch, chicken scratch childhood handwriting saying, I'm proud of your decision to go to war. And then there's a photo or not a photo, there's a drawing, a stick figure drawing of the two of them. She's like George W. Bush. Our parents must have had such a hard on for George Bush.

[Lauren]

They did.

[Chandler]

Because I mean, for him to figure so prominently in your six year old brain.

[Lauren]

I think what happened, if we can just go there for a moment, is that we had watched a really stirring 60 minutes and I felt compelled to, to craft a letter. So I love 60 Minutes. Even at that young age.

[Chandler]

We, you know, we discuss this letter anytime we get the chance on Pop Apologists because it is iconic. And you know, he wrote back, so.

[Lauren]

He did, he did. He wrote me back something really nice. I didn't know that's private.

[Chandler]

Yeah, I didn't know that. Presidents right back to their fan mail or they have some, you know, intern, you know, basically churning out letters.

[Lauren]

I mean, and he says, Mrs. Bush and I join you in X. I think it was from him.

[Chandler]

Okay, so they had private correspondence and our mom literally framed the letter.

[Lauren]

It's still framed in our house.

[Chandler]

Yeah, it is. Anyway, okay, let's get back to Lily though. Actually, let's play a little you. You.

[Lauren]

Okay, so now let's get into kind of what's going on behind the scenes in her personal life.

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[Lauren]

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[Lauren]

Okay, so now let's get into kind of what's going on behind the scenes in her personal life while, you know, some of this music is coming out. So by the end of the 2000s, Lily has achieved, you know, what most people can only dream of. Hit records, awards, full blown celebrity status. And at the age of just 25 in 2010, she announces that she's quitting music to focus on her personal life. And she says, you know, she says, I want to get married and have.

[Chandler]

Kids, drive them to school.

[Lauren]

She's, she yearned for the stability that she missed out in childhood. And so she was ready for that stage in her life. And this began with her boyfriend, Sam Cooper.

[Chandler]

Yeah, so she, I guess always kind of Dreamed of, like, a quiet life in the countryside with a husband and children because of the way she grew up. And so they got pregnant. She was expecting her first child, a son they were planning to name George. And trigger warning. So, you know, the rest of this episode, and we're about to mention pregnancy loss, and then there's also some sexual assault. Yeah. So just trigger warning everyone. They were expecting their first child, a son they're planning to name George when she gets this viral infection.

[Lauren]

So, yeah, she talks about this time, obviously, in her book, and they believe that this infection potentially started with a cavity. And so everything was going along normally in her pregnancy. And then she experienced some spotting. And the doctor said, you know, that my. You know, no need to really worry, but we'll just have you come in. And when they. When they examined her, they saw that, I think her cervix was, like, already. It was either the position or the size. Like, it was, like, ready for delivery. And so they said, you're not leaving this hospital until you give birth. You know, like, so you're now kind of. You're going to be here, and we're going to be monitoring you, trying to keep your water from breaking.

[Chandler]

Okay.

[Lauren]

And so they actually, I think they even did like, a stitch or something to kind of keep her. I don't know. I don't know all the anatomy I should, but whatever. I don't know. To keep, you know, her things in place. Okay. If you will. And she says that she felt that stitch break, actually. She was, like, laughing. She felt that stitch break, and then her water broke and that they were like, okay, well, we're gonna deliver the baby. And that the, you know, devastatingly, the. At one point, the umbilical cord was wrapped around the baby's neck, and the baby was so small they could not, you know, get the baby out manually. Okay. And so traumatic. We don't need to get into all of the details, but the baby passes away, and she still has to deliver the baby.

[Chandler]

Oh, my gosh.

[Lauren]

And it's just like this. This horrific experience, you know, so devastating to have this baby that, you know. Yeah. Just beyond. Beyond. And it. This just sort of, you know, is. Is such a huge moment in her life. She says this is. This was the first moment in her life where she was like. I think where, like, life became very real to her, where it was like, this is. I'm, like, I'm a person. I'm a human being who's experiencing, like, very, very real pain. And it's just. It's so. It's so sad and I can't even imagine experiencing something like that. And the trauma of that physical experience, it's unfathomable.

[Chandler]

So she actually talks a little bit about the grief after that experience. She says it's not something you get over. And she described the depth of her despair in an interview with the Guardian, where weeks after her son's death, she walked out into her garden in the pouring rain, removed all her clothes and just lay naked on the ground and howled in grief. Despite this painful experience, Lily continued to build the family she longed for. So she and Sam became pregnant again and got married in June 2011 in a small ceremony. In November 2011, she gave birth to daughter Ethel Mary. Ethel had a difficult start, so she was born with the airway condition laren Laryngo malassia, I'm sure I pronounced, I mispronounced that. She struggled to breathe and lacked the energy to gain weight, leading to months of tube feeding. And Lily said she became extremely anxious during this period. Practice practically force feeding her at times because doctors warned that Ethel was losing weight. And her previous pregnancy loss made this fear even more intense. So eventually, after medical treatment and operations, Ethel recovered and she is now healthy. And a second daughter, Marnie Rose, was born just two years later in 2013.

[Lauren]

Yeah. So Lily later admitted that motherhood was a lot harder than she was expecting and that she felt unprepared for parenting. Yeah, you know, she hadn't really been around babies before having her own. She says, quote, neither of my parents were particularly good at parenting, so I. So it wasn't a skill set that I had. I sort of assumed that it would just all happen naturally and it didn't. And I think that was the trigger for my postnatal depression. My whole childhood I'd been dreaming of this 2.4 children living in the country, everything, you know, just falling into place and that I'd be this perfect mom and it didn't happen. And I was just very shocked and disappointed.

[Chandler]

Yeah.

[Lauren]

So. And I think in the UK they call it postnatal depression, but it's the same as postpartum.

[Chandler]

And, you know, that's obviously, it's not surprising that she's. That she experienced that, given what she suffered with losing George and then her first daughter having this crazy health issue. It just would be extremely traumatic.

[Lauren]

Yeah.

[Chandler]

So by 2012, after two babies and years away from music, Lily said that she felt she had lost her sense of self. The normal domestic life, while filled with love for her children, left her quote, unfulfilled professionally. She was also facing financial pressures to continue to support her family.

[Lauren]

A couple of things here I want to talk about.

[Chandler]

Okay.

[Lauren]

She has always kind of struggled with her relationship with money. Talks about this in the book. She's quite honest about it. You know, the fact that she likes to spend money. She goes into debt. At one point, she talks about how this is just from her early years. She did not ever adhere to any parking rules, and she racked up $10,000 worth of parking fines and tickets to the point where she was like, there were, like. It was like she had to go to court and there was bail or something. Like, it was bad. It was really bad. And, like, when. When she got one of her first checks, the first thing she did was, like, pay her mom back for her tickets. She has an avoidant, you know, response to all that. She, like, hides bills under her bed, everything. And. And so then I think when she does need to go back to work, when she does decide to go back to work, she really did need to financially support their family. Sam was not the breadwinner.

[Chandler]

Yeah, I feel like this might be a really stupid aside, but I'm gonna. I'm gonna share it anyway.

[Lauren]

I feel like.

[Chandler]

I remember there's this one time in college when my friend and I had an essay due the next day. And I remember it was, like, getting late, and I was like, we have.

[Lauren]

To do this essay.

[Chandler]

And my friend went to bed, and she was just like, no, I'm just gonna, like, talk to the professor. And I. I. This moment clicked for me when I realized that there are certain people who. They just kind of, like, don't see the rules as, like, they don't. Like, they don't have this instinct to follow the rules. And I remember I also talked to this other friend who talked about how he got into a bunch of credit card debt. And then he was just like, yeah, but they just. Eventually, like, you just negotiate with the debt collectors. And it's just like, the same people, their brains just function differently when it comes to, like, abiding by, I don't know, like, the rules.

[Lauren]

Yeah. I think some people don't have crushing anxiety, or if they do, they are able to compartmentalize it or put it.

[Chandler]

Some people are master. Compartmental reason are truly unbothered.

[Lauren]

I think for me, the. This, like, the essay example, the stress of not doing the essay is worse to me than whatever consequences from not doing it.

[Chandler]

Like, it was the first time it had entered my brain that you could just not do. Like, for me, it's. If I don't do it, it's a failure. I'm not, I'm. It's an F. I'm not going to try to talk to the professor to turn it in later.

[Lauren]

I think I became a little bit better at that type of, you know, not following the rules. When I began to fail classes in college, I never, I never failed any classes.

[Chandler]

But to get D's and C's. You did get some D's and C's?

[Lauren]

Yes, totally. I got a couple of, let me just tell you, D's. Get degrees first to let you know. I knew that in my particular field, my GPA was not going to matter. So in my last like year or two, I absolutely got. I got some Cs. I think I got one or two Ds. But anyway, it was kind of a powerful moment. I mean, taking back my power.

[Chandler]

Yeah. I'm so impressed.

[Lauren]

Thank you. I knew you would be. So anyway, back to Lily.

[Chandler]

Back to Lily. So after a few years hiatus, so she says in her memoir. Which memoir? Her memoir. The dichotomy between going back to work as a pop star and being a mother other to two very young children was my waking daily reality. And I found it blindingly difficult, essentially. And she described herself during this time as in a fragile state, very lonely and lost.

[Lauren]

So after this hiatus, she reemerges in late 2013, kind of in a low key way. She does a cover of Somewhere Only We Know, the Keen song. I came across a fallen tree I.

[Chandler]

Found felt the branches of it Looking.

[Lauren]

At me.

[Lily Allen (Memoir excerpts)]

Is this the place we used to love? Is this the place that I've been dreaming of?

[Chandler]

Oh, simple thing I came across.

[Lauren]

That's the song kind of slap. It's an incredible song. I never want to hear your rendition. And it was for the John Lewis commercial, which is. John Lewis ads are very famous in the ad world. Oh, really?

[Sponsor/Ad Voice]

Yeah.

[Lauren]

Because people like wait all year for them.

[Chandler]

It's like it's going to be this.

[Lauren]

Year'S John Lewis ad. They're always just like. They're like sweet and about animated teddy bears and stuff. Nerds. Nerd alert. Sorry, that's just. Just, you know what?

[Chandler]

My brain. Just some industry intel.

[Lauren]

Her return, though, was not necessarily smooth sailing to music. Yeah. So she released the single Heart Out Here and it had a feminist chorus. You know, it's hard out here for a. And it was sort of pointing a message at the music industry. Sexism and body shaming. And she intended it to Be sapphire. But it just satire. Satire said sapphire. I think I said satire.

[Chandler]

No, you got all in.

[Lauren]

She intended it to be satire.

[Chandler]

Keep it all in and you're gonna see.

[Lauren]

She intended it to be satire, and it just totally backfired on her.

[Chandler]

Yeah, maybe I said.

[Lauren]

I think I mixed up the backfired f with the satire.

[Chandler]

Well, thank you for coming clean.

[Lauren]

Yeah, I think maybe some dyslexia happened there. And I'm glad you shamed me. I hope you feel taller now.

[Chandler]

Punching down.

[Lauren]

Honestly, something.

[Chandler]

Is it habit? I would love to leave in 2025.

[Lauren]

I mean, I know you won't.

[Chandler]

Okay, so there's also. There was backlash on social media over this song, and it kind of was a little bit like Katy Perry's disastrous song Women's World.

[Lauren]

It's a woman's world.

[Chandler]

I. I love.

[Lauren]

I play that song every morning.

[Chandler]

It' I'm ready. And I feel so empowered.

[Lauren]

I know you do. I know you do. It's your. Your mom.

[Chandler]

It's your Louise.

[Lily Allen (Memoir excerpts)]

Hey.

[Chandler]

Anyway, we'll play a little bit of how hard out here for everyone except those watching on YouTube.

[Lauren]

Do you have one feminist anthem song that you like?

[Chandler]

No. I find all of them to be so cheesy.

[Lauren]

I know. That's the problem. It's like, I. I appreciate the intent.

[Chandler]

I. I definitely appreciate women's women in the professional sphere, and I want us to continue making money.

[Lauren]

I want anyone believing. Is anyone buying this?

[Chandler]

I want women to be able to have bank accounts.

[Lauren]

I have binders full of lemon.

[Chandler]

This is giving. What is binders for?

[Lauren]

Mitt Romney, like, where he was asked about, like, women in his campaign or something, and he said, I have binders full of women.

[Chandler]

Okay. I love that women can have property, can have their own credit cards.

[Lauren]

You like the credit cards, too?

[Chandler]

Yeah, I sure do. But I just. I don't need any sort of a girl boss, you know, nomenclature. Yeah, I don't need any of that stuff. I find it to be so cringy.

[Lauren]

Even when our favorite songwriters, you know, Ms. Taylor Swift, do it.

[Chandler]

I mean, the man for me is a big. It's a big skip.

[Lauren]

Okay, well, moving on, though. Moving on to May 2014, where she releases her third album, she's this, which was a nod to Kanye West. Jesus. And on the surface, this was Lily returning to the pop game with her signature style of, you know, pop lyrics. And she talks, actually a little bit about the styling of this album, and she says that she was just so busy being a mom and trying to also release new Music. If you look up the album cover for she's this, you might, this might add more context as I'm talking, but she was just like, I'm passing this off just like somebody else, somebody else can like come up with the mood board. And it's a, it's a, it's quite a departure I feel like from, from her previous stuff. Okay. Yeah.

[Chandler]

This is certainly different.

[Lauren]

Yeah.

[Chandler]

Yeah.

[Lauren]

So anyway, I don't think she, I don't think she felt as connected to the imagery from Jesus. Yeah. I want to talk now about what starts to happen on the she's this tour while she's touring this album. Because this is where the, the wheels come off the bus and her mental health really kind of starts to unravel.

[Chandler]

Okay.

[Lauren]

So she's on tour with, you know, with her band, with everybody and her Sam is, is at home, you know, taking care of their, their two daughters. And she really just spirals into some destructive habits here. She, you know, she said she was self medicating with, you know, alcohol and Adderall. And then she also goes on to say that she started to kind of use sex as a way to self medicate and she started to sleep with women and to, you know, step out on her marriage.

[Chandler]

And she kind of told herself female sex workers.

[Lauren]

Yeah, she tells herself that, you know, it's, it's not cheating because it's with women. I don't think it then, it doesn't always stay with women. And then she says, you know, she, she really just wanted him to come get her and she kind of didn't really even care about him finding out because she just didn't care. She was so. It was so self destructive.

[Chandler]

Yeah, it seemed like it was a little bit like a cry for help.

[Lauren]

Yeah.

[Chandler]

And she wanted him to come save her.

[Lauren]

Right.

[Chandler]

But you know what? Who did come save her?

[Lauren]

Okay, so this story is really quite crazy because she's in this self destructive period and she goes to a party in, in LA and she's just getting super drunk and she's just not well at all. And at one point she says that like her and Orlando Bloom have been flirting. She's like straddling him, I think, and like sitting on top of him. And then she goes into like lean in closer to his face, but she ends up like headbutting him and then knocking her head back and hitting something else. And she like passes out and she wakes up to I think maybe Kate Hudson, just like Kate Hudson and Chris Martin like standing over her. She's in the kitchen. They're, like, trying to, like, tend to her.

[Lily Allen (Memoir excerpts)]

Oh.

[Lauren]

Chris Martin then drives her home. She wakes up in the morning, and there's a note on her fridge, says, lily, you know, call me. Chris with his phone number. Crazy. And she calls him, and he says, hey, like. Like, come out to have Sunday lunch with Gwyneth and I. And they're in the process of unconscious uncoupling. Oh, they are?

[Sponsor/Ad Voice]

Yeah, they're full.

[Lauren]

That the conscious uncoupling is, like, happening.

[Sponsor/Ad Voice]

Okay.

[Lauren]

But she goes out to their house in, I believe, Malibu or wherever.

[Chandler]

It's Beach Malibu.

[Lauren]

And she says that, you know, it was really wonderful. You know, they have this amazing garden that goes from the top of the cliff down to the sea. And Chris is just like, really? Chris and Gwyneth are both really nice to her. And he grabs her and says, come on, like, I want to take you for a walk. Let's, you know, let's go down. I'll take you for a walk down by the beach. And I was like, okay, this is Lily. She says, okay, I thought. You know, he's very sweet for taking the time. What she doesn't realize at the time is that this is kind of his gentle way of saying, you need help. Like, when they get down to the beach, he kind of says, you know, clearly, things are not right and you're not well.

[Chandler]

Yeah.

[Lauren]

And I think that, like, I don't know. She says that she'll always be really grateful to Chris Martin, you know, in that time. And he's not really mentioned as, like, her good friend before this or anything.

[Chandler]

Yeah, I don't know.

[Lauren]

I. That. That story. Another. Another point for Chris Martin. I don't necessarily expect a guy who's not romantically involved with another woman who's not really close friends with her to kind of take it upon himself to try to, like, have a little intervention with her when he sees that she's clearly unwell.

[Chandler]

Yeah. And I also think that it would be so easy, you know, to witness this behavior and honestly just be, like, not my problem.

[Lauren]

Kind of messy.

[Chandler]

Not my circus, not my monkey. And the fact that Gwyneth and, you know, Chris essentially staged his intervention. I mean, I. I'm gonna. I'm gonna give all the credit to Gwyneth. I'm sure it was all her idea, but she probably just knew how mortified Lily would be if she brought it up. Yeah. She was like, let's just do lunch. I'll have a macrobiotic meal. You guys can take a walk to the sea. That was a stupid thing to say, but honestly, let's just keep it in, whatever.

[Lauren]

No, I mean, I, I'm, I'm giving all the credit to Chris because I think, you know, I think at one point they were on the same record label and obviously he's from the uk, you know.

[Chandler]

Yeah. Okay.

[Lauren]

I just.

[Chandler]

That makes more sense.

[Lauren]

I find, I find this. You're just sorry. Are you hurt by the fact that I can't give credit to Gwyneth in this moment?

[Chandler]

Do you feel like I'm personally offended?

[Lauren]

Yeah.

[Sponsor/Ad Voice]

I don't know.

[Lauren]

I just. I find this story to be very touching.

[Chandler]

Yeah.

[Lauren]

Okay.

[Chandler]

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[Lauren]

You kind of need a new signature scent. I've been saying that I love entering.

[Chandler]

The new year with a fresh signature scent.

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[Lauren]

And if you still have names on.

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[Chandler]

So she says that she was at her lowest of lows at this time. And when asked if she if she wanted to get caught cheating, Lily said, no. I was pretty brazen with all my behavior. I think I just didn't care, actually. Maybe I did want to get caught. Maybe I wanted Sam to rescue me. I wanted him to find out about these things and say, enough is enough. You're coming home. So Lily and Sam divorce, but not before he made her tell him every single detail of every infidelity. Because he needed to hear it all. They agreed to break up while sitting in a dark corner of their favorite Italian restaurant in the summer of 2015. As she describes it in the book, we were both miserably sad. We were both in tears. We both felt some kind of relief. Yeah.

[Lauren]

And I wish I could say this is kind of the end of some of her troubles. No, but it's not. In November 2015, she's trying to sort out her life, and she meets a man who, you know, she refers to in the book as record industry executive. No other, you know, moniker she wanted to name him, but. But her publisher's lawyer said she couldn't. And I think if I remember right, they. She says, like, hey, I'm gonna check into a facility or I'm gonna start going to rehab tomorrow. And he says, okay, great. Let's celebrate tonight. Then they get drunk on some tequila, and, you know, the next day, she has a bad feeling. She doesn't really remember getting home. She decides to write it off. She met up with him again for work, and alcohol is involved. And she wakes up to find him trying to have sex with her in a hotel room. She's naked in his bed.

[Chandler]

Yeah.

[Lauren]

She once again felt compelled to write it off. I think that's unfortunately, you know, an instinct that women have is that they just want to, you know, write it off. But she does go to her lawyer in London, and she signs an affidavit saying what happened. She just.

[Chandler]

Just.

[Lauren]

She kind of wanted to know that.

[Chandler]

It was on record.

[Lauren]

It was on record, and she wasn't ready to, like, take it any further than that, but that it was on record that this had happened.

[Chandler]

Yeah. She also endured some terrifying stalking. So There's a man named Alex Gray who began harassing her in 2008, and he ultimately broke into her London house in 2015 while she and her children were sleeping.

[Lauren]

This story is crazy. Yeah. If I may.

[Chandler]

Yeah, please.

[Lauren]

So she is dating somebody. New post divorce nurse. His name is Dan. And they are, they're like in bed together. I think they're like having sex or anything, but they're like in bed. And she remembers that like he was kind of spending the night in sort of a covert way because he wasn't. It wasn't time for him to like meet her daughters. So she had her bedroom door locked because she didn't want her daughters to like come in and see a random guy. So they're in bed together. It's like 1:00am, 2:00am and all of a sudden someone's banging on her bedroom door.

[Chandler]

This is insane.

[Lauren]

And why she's like so confused. She thinks it's Sam, her ex husband. She thinks, oh, oh my God. Sam's come by the house. He sees, he's gonna. He knows that I'm with another guy. Yeah, he knows. Even though we're divorced or whatever. He's so upset that I didn't tell him or whatever. And she opens the door. She goes and opens the door and this guy comes in and starts screaming at her and says, you know, you know who I am? How do you not know who I am? You know? And to the point where her. He's not immediately violent. To the point where Dan, you know, her new boyfriend says, like, who is this guy? He says, he, you know, you know him. And she's like, I don't know him. I do not know him.

[Chandler]

Yeah.

[Lauren]

And she says, like, I don't know him. You have to get him out of here. She thought that she maybe had an. He potentially had a knife because he was kind of concealing something in his jacket. Her boyfriend Dan is able to get him out of the house. They call the police. The police come. They're kind of not buying it. They're kind of like, whatever. She realizes that he, that her purse is gone, that he's like stolen her. Her purse, this guy. So the police are like, oh, yeah, well, it was just a robbery. She then goes back into like her correspondence and you know, and sees that the guy who came to stalk her was actually this man named Alex Gray who's been emailing her crazy things about how he. He says he wrote the Fear. Wow. And that he wants to kill her. I think that that would have been.

[Chandler]

Even more horrific in the moment for her, she realized who it was.

[Lauren]

Totally. So he had started harassing her under the handle Lily Allen, RIP and claimed to have written the song the Fear.

[Chandler]

Yeah.

[Lauren]

And it increased from letters to abusive rants. Accusations like sending letters to management. She says he would drop off these letters at my record company, my management offices, my sister's shop, and flat. It was freaking me out a bit. And I'm not easily scared, so the fact that I went to the police with the letter shows how serious I felt I was.

[Chandler]

But the police really do nothing.

[Lauren]

Yeah, they, like, I. So I think eventually he is. He is prosecuted and, like, sent away to a mental facility. In fact, she goes to his hearing, his bail hearing, and where the judge says, you know, should I grant you bail?

[Sponsor/Ad Voice]

Or whatever.

[Lauren]

And he continues to make threats at her in the courtroom, but she says, I was so grateful that he did that because it showed that he was really not well, you know, mentally not well and unsafe and dangerous.

[Chandler]

Did he threaten you?

[Lauren]

He did.

[Lily Allen (Memoir excerpts)]

When the judge said, why should I grant you bail today? He said, because the world be a better place without her. And that's what I'm here to do.

[Lauren]

I think, like, all of these stalking cases, we've talked about a few of them on our podcast. It's just so scary and really, like.

[Chandler]

The consequences can be deadly.

[Lauren]

Consequences can be deadly. But also, there's not very many consequences before something deadly happens.

[Chandler]

Yeah, completely. Which is so, so, so terrifying. So after Lily says this, after this moment, she kind of hits rock bottom. And in 2016 and 2017, she begins writing new music, channeling the turbulence of her recent years into her songs. She releases her fourth album, no Shame, in 2018. This album had her at her most vulnerable and honest, writing about heartbreak, motherhood, insecurity, and substance abuse in a style that read like diary entries.

[Lauren]

Yeah. And I'll just say, like, post this stalking around 2016, she. She really. There is, like, it's. There was the rock bottom with Chris Martin, and then there's the rock bottom that comes, like, post divorce, post everything else, where she. I think she, like, checks herself into a facility. Wow. For all of these things. And this is where I think she really does get sober.

[Chandler]

Yeah. So the album's lead single, Trigger Bang, addressed stepping away from her toxic party life, while the song three imagined her life from her little daughter's perspective. Critics loved the album, noting it as a brave, immature evolution for Lily. And it received much better reviews than J. No Shame also won the Mercury Prize, which is the British album of the year, very prestigious award, but it didn't have much commercial success. It peaked at number eight in the uk, making it her lowest selling album at that point. But it had a ton of critical acclaim.

[Lauren]

So I, like, listen to all of her albums. Yeah, this one, it has a couple that I really like, but it's not. Maybe fewer earworms.

[Chandler]

Okay. So during this time, she releases her memoir.

[Lauren]

Memoir.

[Chandler]

Memoir. My Thoughts Exactly. To accompany no Shame, she wrote about many things that were mentioned in the album. Her grief, trauma and infidelities, but also dropped bombshells like a previously unknown affair with the Oasis member Liam Gallagher while he was married.

[Lauren]

So this is a quick little story. It's so crazy. She has sex with him while they're at a festival in Japan. I want to say, okay. And he's married at the time. And I think he says to her after this, like, you know, you can never say anything about this because of so and so. I'm blanking on his wife's name. Years later, maybe, maybe it was only months later she gets a call from him randomly where he says, hey, hey, hey, I'm on the phone with you. You know, nothing happened between us, right? For real?

[Chandler]

Oh, my gosh.

[Lauren]

Wow.

[Sponsor/Ad Voice]

Isn't that crazy?

[Chandler]

So what did she do in that moment?

[Lauren]

She was like, no, I think she said, like, yeah, whatever.

[Chandler]

Nothing happened. Wow.

[Lauren]

Yeah.

[Chandler]

And then she.

[Lauren]

And then she's, you know. Yeah.

[Chandler]

Do you know if he and his wife were together when this book came out?

[Lauren]

I did the work, but not that much work today. I think the book is very candid, obviously. I have, you know, I have all these stories now from it that, you know, you wouldn't know about her before this. And she says that she really wrote it for her daughters because she, like, it's not for her, it's for her daughter. She didn't want them to, like. Like, I think, find out things from the tablet rather than just hear it from her.

[Chandler]

She also gives a quote where she kind of says that if you tell everything there is to know, then people can't really come after you. And so this is her, you know, describing that.

[Lily Allen (Memoir excerpts)]

Basically, I sort of figured out when my marriage broke down and things were really bad that actually if you just, like, tell everyone everything there is to.

[Chandler]

Know and then they can't come after.

[Lily Allen (Memoir excerpts)]

You and they can't follow you anywhere.

[Lauren]

So you understand they're not going to.

[Lily Allen (Memoir excerpts)]

Find anything more sensational because you're like, I was sleeping with prostitutes.

[Lauren]

And in talking a little bit more about her choice to get sober. She says, I really. Or she says, I can really miss those extreme highs. I miss being on the pyramid stage at Glastonbury and rushing my tits off. I know that I will never experience that again. And there's a sadness that comes with that. But I am level. I'm no longer having really terrible, long periods of time of absolute despair.

[Chandler]

She also shares some of the best parts of sobriety, saying, In 2024, I'm a much more connected and present parent, which is amazing. I got text from Ethel yesterday, her daughter, and she was very clear. These are the things I'm feeling. I'm sad, I'm upset because of this. And I was like, oh my God, I'm winning at life. She's naming her emotions and she's asking me for help. My relationship with my kids specifically is much better since I got sober.

[Lauren]

Moving on to more recent Lily Allen times. You know, and it's crazy kind of now doing this deep dive on her, knowing what we know, listening to her book, knowing what I know about, you know. Her most recent wasn't, you know, married to David harbour. So in 2019, she matches with David harbor on Raya and they hit it off. David says they connect over a similar humor and her vibrant spirit. He says, quote, lily lives with a color in a deeper way than most. She has such a presence and star quality.

[Chandler]

In September 2020, so this is a year after they met, they eloped in Las Vegas. So they got married by an Elvis impersonator with Ellie's daughters in attendance as the only guest. The low key wedding seemed like a perfect reflection of who Lily was. They just got in and out afterwards. As a new stepdad, David seemed to bond with Ethel and Marnie and the new family attended the Stranger Things season four premiere together in 2022. Lily at this time was splitting her life between London and New York. Since David worked more in New York during these years, she worked on projects outside of music. So in 2019, she made a cameo playing herself in the film how to Build a girl. And in 2021, she made her debut on London's West End stage. Lily impressed theater critics and even earned a Lawrence Olivier Award nomination for Best Actress around this time. She and her longtime best friend Makita Oliver launched a podcast in 2023 called Miss Me.

[Lauren]

So we all know about this play now. We all know about what was happening during this play. The play, you know, is pretty soon thereafter. Getting married about a year after them getting married when really? Yeah, it's in 2021. That she's in the play. And they got married in 2020. I think they got together 2019, 2018, maybe. I. I get.

[Chandler]

No, 2019 they get together or 2019 they match on Raya. 2020 is when they get married. I guess it kind of tracks with a David harbor that he's not going to be able to keep that together for so long, you know?

[Lauren]

Yeah. Yeah.

[Chandler]

So by 2023, fans began speculating that Lily's marriage to David harbor was on the rocks, and she had gone quiet about her husband online, even unfollowing him on Instagram. That's a move that definitely can tell you something.

[Lauren]

Yeah.

[Chandler]

In interviews and on her podcast, literally dropped hints that things were not going well for her. And in March 2024, she talked about the types of men she had pursued. She said, because I will always just, you know, have daddy issues, don't I? I just want a big old hairy daddy forever. That's all I want. I know who my dad was, and my dad was sort of there, but not there. So I think that you. Yours was slightly a fantasy, whereas mine was, like, trying to recreate something that existed. Hence the obsessions.

[Lauren]

She talks about this as well on the album, you know, about how those daddy issues have kind of. Yeah. Fully informed the men she's dated. Quick little story about. At one point, I think she even dated or at least slept with a man who knew her dad, who was like. Or, you know, and her dad sort of freaked out when he heard about this. And that man used to be married to Sam Taylor Johnson.

[Chandler]

Oh, wow.

[Lauren]

Who, you know, who's married to.

[Chandler]

Yeah, who's married to that young guy.

[Lauren]

The young guy. Anyway, just like, crazy, but heard his dad. When her dad found out, he was upset about it, but then it sort of became like a running joke.

[Chandler]

Interesting.

[Lauren]

And I think that was, like, obviously, that's, you know, kind of gross.

[Chandler]

Yeah. Yeah, definitely.

[Lauren]

So.

[Chandler]

In February 2025, multiple sources confirmed that Lily and David had separated, with one insider telling people that her marriage had been crumbling and that they have split. Lily sought help for her mental health to regroup and preemptively shot down rumors that it was substance abuse related. She said, I'm not going to rehab. I've not relapsed. I don't know who's spreading this vicious. These vicious rumors, but they are not true.

[Lauren]

Then in, you know, this most recent fall, 2025, Lily tells Vogue that the past few months have been turbulent, but that she's trying to stay really strong for her daughters. She's asked if David would remain in the girls lives. She says, you'll have to ask him. She also noted that her and Sam Cooper, you know, have a friendly co parenting rhythm.

[Chandler]

During this time, she poured her heartbreak into her music. She recorded her fourth album, West End Girl, in 16 days in December 2024, where she takes listeners through the past four years of her life. It is, as the New York Times says, a successful, salacious account of a marriage in which a husband systematically cheats on and gaslights his wife.

[Lauren]

Lauren and I talked about the album a couple episodes ago, kind of when it first came out and it was making it splash. I love it. I'm still listening to it all the time and I. I'm just so happy to see that it's getting so much like continued traction and acclaim because she really deserves it. And I, you know, she. I think I go back to the fact that she picked up her whole life and moved for David Harbour and started this whole new life with him. And for him to really then just be in, to dismantle their marriage a year in. It's unforgivable.

[Chandler]

No, it absolutely is. And I think what's so striking about the album is that it's confessional in a way that most songwriting is not. Like most songwriting, there's storytelling happening and there's elements of, you know, fiction. And in this, this, it's just so. It's basically dire entries.

[Lauren]

Yeah.

[Chandler]

Music.

[Lauren]

It's very literal.

[Chandler]

It's very literal.

[Lauren]

Yeah. You know, and I think now, having done this research on her, having listened to her book, read her book, I think that I have a lot more empathy for her. I know people have said, you know, she cheated on her husband and she did, like she's, you know, she was not faithful to Sam Cooper.

[Chandler]

Yeah.

[Lauren]

And I'm glad that we've kind of painted a complete picture of who she is, but I. I can't help but feel kind of deeper empathy for her. And in, you know, I think we, like, made some comments when we were first talking about the album about how, you know, if your husband wants an open marriage, run in the other, run to the divorce lawyer's office. But kind of now knowing her story, the men that, you know, that have been in her life and kind of like the way that her relationships have failed, she probably really did want this one to work. Yeah. And so when this idea was introduced, it was like, you know, I love this man deeply and I want this to work. And so, I don't know, I have more empathy for Her.

[Chandler]

Yeah. Did you know that on Tick Tock we have a clip of us talking about the open marriage and we're like, you know, we're not open minded when it comes to open marriages. And there's a lot of people that have remixed that. Like people in open marriages that are like, responding. Do you know that?

[Lauren]

I did not know that.

[Chandler]

And there's like therapists for open, open relationships that are weighing in on us not being open minded. Anyway.

[Lauren]

I have empathy. I'm not. I'm not any more open minded on. On open marriages.

[Chandler]

Yeah.

[Lauren]

Well, that aside.

[Chandler]

And you know, our Tick Tock aside, the Guardian gave West End Girl a five star review, calling it the out, calling it a gobsmacking autopsy on a marital betrayal that is cathartic and brutally candid, but also stylistically varied with melodies and sparkle. In its own way. Western Girl really is this culmination of everything Lily Allen represents. Unfiltered honesty, dark humor, and turning these chaotic parts of life into art. Rolling Stone said West End girl has made listeners reassess their own experiences of love and loss by witnessing Lily lay hers bear. And one of the. One of the great parts of the album, I think is really when she discusses, like, I think it's in the song let you win. And she says, like, if, like, as long as I can just say what happened to me, I can leave with my dignity.

[Lauren]

Yeah.

[Chandler]

That's not the exact lyric.

[Lauren]

Not keep your secrets. Yeah.

[Chandler]

And what I find that's great to me about this album is not just like this, the salacious quality of it. I think the songs really slap, like Dallas Major got so stuck in my head. So many of these songs are, I think, are really, really good on their own.

[Lauren]

Yeah. And they're like, honestly lovely at times. A little sad, but lovely to listen to.

[Chandler]

Yeah. So if you have not listened to West End Girl, what are you waiting for? Please, you know, as we conclude this episode, turn on West End Girl, give it a spin. And I will say, you know, not happy for Lily that. That essentially this has been the turn of events. I'm wishing her a stable future and I'm wishing that, you know, we get her, we get her life of a showgirl, you know, her in love, happy album.

[Lauren]

Her opalite.

[Chandler]

Yeah, her opalite. I hope she only has. I hope her Onyx nights are coming to an end or have concluded. I like how we just have to end on a note about Taylor Swift. We try to talk.

[Lauren]

I thought we had enough. And then you just continued with her onyx nights.

[Chandler]

We try to, we try to talk about other people but. But all roads lead back to yeah, you know, it's a sickness. It's a mental to Taylor Swift. And with that said, you know, to conclude this, Alan deep dive, we're so excited for the ERAS tour document to come out. Love you guys.

[Lauren]

Love you. Bye Bye. Stream blockbuster hits like 21 Jump Street Ted, the Expendables and so much more on Pluto TV. Stream now pay Never this thing on. I'm Kaitlyn Bristow, host of off the Vine Podcast where I get real, maybe a little too real sometimes with my friends and celeb guests from Bachelor franchise and beyond. I'm talking guests like Jonathan Van Ethan. Na na na na na na na.

[Chandler]

Na na na na na na na.

[Lauren]

Nikki Glaser, Wells Adams, Elise Meyers. Just like in this like business jacket. Like I would love some tacos. Heidi d', Amelio, Big Brother's Taylor Hale. I have to bring it up because it happened and we're going to get through it. What I do and so many more. So come hang out with us, hear ridiculous confessions and get a little vulnerable because you know what? We're all just just floating on this weird little planet together. Follow rate and review off the Vine Podcast wherever you listen to your podcast.

[Chandler]

Okay, so I just got done with such a sweet Thanksgiving with Kagan and the family and it was such a wonderful time. But right now it is a moment where I am just in my resting era before true holiday madness sets in. And as I cozy up up, I want to be as comfortable as possible, which is where Macy's cashmere comes into play. I am just loving their everyday cashmere. They're so luxurious. These pieces are soft, they're warm, they're effortless, and they have so many silhouettes and they come in over 40 colors. I think you can incorporate cashmere in such an elegant way into so many holiday outfits. A beautiful cashmere sweater with a midi silk skirt is such a classic, pretty polished look. I also love a cashmere sweater and jeans for a little bit more of an effortless vibe. Macy's friends and family event is also going on right now through December 11th with 30 to 50 off fine jewelry. So I'm gonna buy some new pieces to add an extra layer of lux and sparkle to all my cashmere looks. And with 15 off beauty, I might even treat myself to a new fragrance. I love entering the new year with a fresh signature scent.