Chicks in the Office: Chelsea Handler Talks Roasting Leonardo DiCaprio & Critics Choice BTS, Her Favorite Drugs + More!

Date: January 7, 2026
Hosts: Rhea (Ria) & Fran (Barstool Sports)
Special Guest: Chelsea Handler

Episode Overview

In this vibrant episode, Rhea and Fran kick off the new year with pop culture chatter and a dive into their personal routines before welcoming comedian, author, and Critics Choice Awards host Chelsea Handler. The conversation ranges from Chelsea’s approach to roasting Hollywood royalty, behind-the-scenes awards show stories, and her signature candid takes on drugs, family, and life. The hosts also dissect the Ashley Tisdale “toxic mom group” controversy and dish on the latest Housewives drama, pop culture hot takes, and more.

Key Discussion Points & Insights

1. Surviving the Post-Holiday January Blues

[01:16–12:00]

Fran and Rhea share their struggle with the monotony of January in NYC: "January is the Sunday of the week." – Fran [03:02]
They discuss what days of the week each month “feels” like, and how routines and little joys (like using a fancy espresso machine) can lift the mood.
Espresso-making hijinks: Fran recounts her journey with her new Breville Barista Touch machine, the struggle to get coffee just right, and the newfound respect for baristas.
- "A really good espresso shot will change your morning. A really bad one, you want to puke over the second." – Fran [10:23]
Rhea details her new Dyson vacuum and shared dog-hair woes: “It’s just the little things. You’re like, wow, this thing really fucking works.” [17:54]

2. New Year's Epcot Revelations

[19:33–22:54]

Viral TikTok videos show New Year’s Eve at Disney’s Epcot as "an absolute time," with unique DJ parties in every country pavilion.
Hosts share their mixed feelings: the event looks wild, but the size of the crowds seems “like my nightmare.” – Fran [21:27]
Noah wonders if they celebrate midnight in every country’s local time: “That’d be kind of fun, though.” – Noah [21:00]

3. Pop Culture News Corner

Ashley Tisdale’s ‘Toxic Mom’ Clan Drama

[25:44–38:47]

Deep dive into Ashley Tisdale’s essay about leaving a “toxic mom group,” and the internet’s subsequent sleuthing and leaps to conclusions.
Speculation, rumors, and the dangers of assumptions on social media dissected:
- “Now I gotta know the details – whether it’s about them or not... I want the gossip.” – Fran [31:09]
- The reality of adult friendships and how group dynamics shift: “You think when you move on from high school… that the toxic friend groups disappear. When actually older women can be the most nasty at times.” – Fran [33:49]
Ultimately, her rep clarifies that the public speculation was incorrect, and the drama spirals further.

Real Housewives & Reality TV Updates

[43:13–47:01]

Salt Lake City reunion trailer teases drama so chaotic that Andy Cohen “walks off” set.
- “It’s almost like the teacher in school when they just had enough and walked out… whoa, we went too far.” – Fran [44:20]
Quick notes on the TLC documentary about Mary Cosby and shifting opinions on her as a housewife.

Book & Film Gossip: The Housemaid Sequel & Sydney Sweeney

[49:10–55:05]

“The Housemaid” is getting a movie sequel; hosts discuss mixed reactions to the first film and critiques of Sydney Sweeney’s acting.
Conversation veers into favorite book genres, polarizing book opinions, and how adaptations stack up to source material.

4. Popcorner Hot Takes (Listener Calls & Culture Debates)

TV Spoiler Frustrations & Bachelorette Speculation

[56:44–59:37]

Listeners lament the challenge of avoiding spoilers for the upcoming “Bachelorette” with Taylor Frankie Paul, given her public profile.

YouTube, Billboard, & the Future of Music Videos

[59:37–68:18]

A caller asks how the removal of YouTube streams from Billboard charts will affect music and music videos:
- “I always thought it was just like listening, streaming, radio. I didn’t even think of YouTube.” – Fran [60:56]
- Hosts conclude music videos probably aren’t going anywhere (“I always love a music video…” – Noah [64:28]) but discuss the shifting landscape and convoluted music licensing issues for creators and businesses.

Awards Show Hot Take: Should Repeat Acting Wins Be Allowed?

[68:21–72:10]

Caller suggests actors should only win once per role. The group disagrees, arguing new seasons bring new challenges, but appreciate the idea as a debate-starter:
- “Different storylines, your character can go through so many different things.” – Fran [69:29]
- “Almost like participation awards – I’m not down with that.” – Fran [71:01]

Shakespeare, ‘Hamnet’, and Taylor Swift Connections

[73:08–87:59]

Caller Kayla wonders if Taylor Swift (notorious Shakespeare fan) will watch “Hamnet” starring her ex, Joe Alwyn. Fran and Rhea doubt it given the long relationship, but find the question fun – leading to a winding, hilarious discussion of Shakespeare’s real life, pop culture legacy, and the problem of factual gaps in historical biopics.
- “Sometimes you forget Shakespeare’s a real person!” – Fran [80:44]
The hosts admit to feeling exposed about their Shakespeare knowledge, but embrace it: “He’s a star-studded name, and we don’t know much about him.” – Fran [83:07]

FEATURE INTERVIEW: CHELSEA HANDLER

[89:29–128:32]

Critics Choice Awards BTS & Roasting the Stars

Handler describes prepping to host for the fourth time. She loves setting the tone and isn’t afraid to “go in on” big names.
- “I feel very competent at that skill set… that’s my jam.” – Chelsea Handler [91:41]
Most memorable roast: Leonardo DiCaprio, who she knows socially. She also notes that Jeff Bezos “deserves to be shamed.”
- “Leo had the best reaction.” – Chelsea Handler [93:39]
Awards show chaos: Timothée Chalamet reportedly “blowing up the bathroom,” presenting logistical challenges.
On celebrities’ performances: “I love that she [Taylor Swift] just gives her money away to so many different people. How can you say anything negative about a person who does that?” – Chelsea Handler [90:44]

Chelsea’s Whistler Lifestyle & Drug Stories

Handler shares her dual life—workaholic in LA, “homeless” ski bum in Whistler with a house full of kids (not hers).
- “Kids like me because I’m not interested. … I want kids to have a person like me in their life to show them what’s possible.” – Chelsea Handler [100:51]
She reflects on learning to ski after an embarrassing double-black-diamond date with a Kennedy-adjacent ex (“I ignored the red flag for two years…”), and taking lessons with both male and female instructors.
Travel, “psychedelic conference” in Antarctica, and her distaste for ketamine.
Ayahuasca experience changed her relationship with her sister:
- “…This voice is talking to me… telling me I had to be nicer to my sister. … It was like an iPod shuffle of memories.” – Chelsea Handler [106:46]

High & Mighty Tour & Advice Podcast

Chelsea’s “High and Mighty Tour” begins in February, focusing on travel, drugs, family stories, and self-improvement.
Praises the liberating power of “editing” family for boundaries and happiness.
Her advice podcast “Dear Chelsea” (soon on Netflix) is about helping people take leaps and “get out of bad relationships,” with a favorite anecdote about quitting pot alongside a caller.

Notable Quotes

“People need to know you can cut people out of your family. Who gives a shit? You don’t have to say it’s forever.” – Chelsea Handler [109:51]
“I like to take drugs around the world and give them to people. … I feel like I’m healing people.” – Chelsea Handler [108:37]
On being direct: “You don’t have to be a cunt about it – you can just say something that’s hard to hear in a nice way.” – Chelsea Handler [118:35]
On Hollywood romance: “I use these award shows in the same way I use my TV: to hit on men I’m attracted to.” – Chelsea Handler on her attempts to pursue Ralph Fiennes [124:28]

Notable & Memorable Moments

Espresso tutorials and TikTok rabbit holes. [08:32–14:23]
Fran, Rhea, and Noah’s confusion over Billboard chart rules and music licensing. [59:37–68:18]
The Ashley Tisdale friend drama spiral showing the unpredictability of social media mob mentality. [25:44–38:47]
Chelsea’s anecdote about legitimately changing her life after ayahuasca (“iPod shuffle of memories”). [106:46]
Jane Fonda once sat Chelsea down to call out bad behavior—leading to a true friendship and personal growth. [118:44–120:37]

Interview Timestamps

[89:29] Chelsea joins the show: pop culture, Taylor Swift, and Critics Choice Awards
[91:41] Roasting celebrities; awards show nerves and tactics
[93:39] Best reactions, BTS logistics (Timothée Chalamet’s bathroom breaks)
[94:59] Oprah, mending impressions, and forgiveness
[99:44] Whistler, the “youth hostel” holiday house, and how Chelsea parents other people’s kids
[101:45] The skiing origin story, conquering black diamonds, and ex-flings as ski instructors
[104:09] Antarctica psychedelic boat trip, ketamine, ayahuasca, and “healing” with drugs
[108:34] High & Mighty Tour and advice for “editing” family
[112:35] Dear Chelsea podcast, call-in follow-ups, and advice philosophy
[119:44] Jane Fonda calls her out: the power of honest female friendship
[124:28] “Using” the Critics Choice Awards to hit on Ralph Fiennes
[125:51] On her past with 50 Cent, gambling in Vegas, and post-show rituals

Final Thoughts & Takeaways

January blues are universal—espresso and Dyson vacuums can help.
Adult friendship politics are as messy as high school; Ashley Tisdale’s story shows the internet is quick to judge.
Chelsea Handler is unabashedly herself, whether roasting A-listers or teaching listeners to set boundaries—her approach is equal parts vulnerable, irreverent, and empowering.
The pop culture world remains unpredictable and captivating, from music charts to award shows to the perennial mysteries of Shakespeare and literary adaptations.
If you need a good laugh, a sharp perspective, or candid life advice, Chelsea’s new tour and Netflix podcast are not to be missed.

Resources / Further Listening

Chelsea Handler’s High & Mighty Tour: ChelseaHandler.com
Dear Chelsea podcast (soon on Netflix)
Chicks in the Office YouTube, Spotify, Apple Podcasts

End of Summary
“January is the Sunday of the week. Some might think it’s the Monday, but in my brain, January is the Sunday…” – Fran [03:02]

Chicks in the Office: Chelsea Handler Talks Roasting Leonardo DiCaprio & Critics Choice BTS, Her Favorite Drugs + More!

Date: January 7, 2026
Hosts: Rhea (Ria) & Fran (Barstool Sports)
Special Guest: Chelsea Handler

Episode Overview

Key Discussion Points & Insights

1. Surviving the Post-Holiday January Blues

[01:16–12:00]

Fran and Rhea share their struggle with the monotony of January in NYC: "January is the Sunday of the week." – Fran [03:02]
They discuss what days of the week each month “feels” like, and how routines and little joys (like using a fancy espresso machine) can lift the mood.
Espresso-making hijinks: Fran recounts her journey with her new Breville Barista Touch machine, the struggle to get coffee just right, and the newfound respect for baristas.
- "A really good espresso shot will change your morning. A really bad one, you want to puke over the second." – Fran [10:23]
Rhea details her new Dyson vacuum and shared dog-hair woes: “It’s just the little things. You’re like, wow, this thing really fucking works.” [17:54]

2. New Year's Epcot Revelations

[19:33–22:54]

Viral TikTok videos show New Year’s Eve at Disney’s Epcot as "an absolute time," with unique DJ parties in every country pavilion.
Hosts share their mixed feelings: the event looks wild, but the size of the crowds seems “like my nightmare.” – Fran [21:27]
Noah wonders if they celebrate midnight in every country’s local time: “That’d be kind of fun, though.” – Noah [21:00]

3. Pop Culture News Corner

Ashley Tisdale’s ‘Toxic Mom’ Clan Drama

[25:44–38:47]

Deep dive into Ashley Tisdale’s essay about leaving a “toxic mom group,” and the internet’s subsequent sleuthing and leaps to conclusions.
Speculation, rumors, and the dangers of assumptions on social media dissected:
- “Now I gotta know the details – whether it’s about them or not... I want the gossip.” – Fran [31:09]
- The reality of adult friendships and how group dynamics shift: “You think when you move on from high school… that the toxic friend groups disappear. When actually older women can be the most nasty at times.” – Fran [33:49]
Ultimately, her rep clarifies that the public speculation was incorrect, and the drama spirals further.

Real Housewives & Reality TV Updates

[43:13–47:01]

Salt Lake City reunion trailer teases drama so chaotic that Andy Cohen “walks off” set.
- “It’s almost like the teacher in school when they just had enough and walked out… whoa, we went too far.” – Fran [44:20]
Quick notes on the TLC documentary about Mary Cosby and shifting opinions on her as a housewife.

Book & Film Gossip: The Housemaid Sequel & Sydney Sweeney

[49:10–55:05]

“The Housemaid” is getting a movie sequel; hosts discuss mixed reactions to the first film and critiques of Sydney Sweeney’s acting.
Conversation veers into favorite book genres, polarizing book opinions, and how adaptations stack up to source material.

4. Popcorner Hot Takes (Listener Calls & Culture Debates)

TV Spoiler Frustrations & Bachelorette Speculation

[56:44–59:37]

Listeners lament the challenge of avoiding spoilers for the upcoming “Bachelorette” with Taylor Frankie Paul, given her public profile.

YouTube, Billboard, & the Future of Music Videos

[59:37–68:18]

A caller asks how the removal of YouTube streams from Billboard charts will affect music and music videos:
- “I always thought it was just like listening, streaming, radio. I didn’t even think of YouTube.” – Fran [60:56]
- Hosts conclude music videos probably aren’t going anywhere (“I always love a music video…” – Noah [64:28]) but discuss the shifting landscape and convoluted music licensing issues for creators and businesses.

Awards Show Hot Take: Should Repeat Acting Wins Be Allowed?

[68:21–72:10]

Caller suggests actors should only win once per role. The group disagrees, arguing new seasons bring new challenges, but appreciate the idea as a debate-starter:
- “Different storylines, your character can go through so many different things.” – Fran [69:29]
- “Almost like participation awards – I’m not down with that.” – Fran [71:01]

Shakespeare, ‘Hamnet’, and Taylor Swift Connections

[73:08–87:59]

Caller Kayla wonders if Taylor Swift (notorious Shakespeare fan) will watch “Hamnet” starring her ex, Joe Alwyn. Fran and Rhea doubt it given the long relationship, but find the question fun – leading to a winding, hilarious discussion of Shakespeare’s real life, pop culture legacy, and the problem of factual gaps in historical biopics.
- “Sometimes you forget Shakespeare’s a real person!” – Fran [80:44]
The hosts admit to feeling exposed about their Shakespeare knowledge, but embrace it: “He’s a star-studded name, and we don’t know much about him.” – Fran [83:07]

FEATURE INTERVIEW: CHELSEA HANDLER

[89:29–128:32]

Critics Choice Awards BTS & Roasting the Stars

Handler describes prepping to host for the fourth time. She loves setting the tone and isn’t afraid to “go in on” big names.
- “I feel very competent at that skill set… that’s my jam.” – Chelsea Handler [91:41]
Most memorable roast: Leonardo DiCaprio, who she knows socially. She also notes that Jeff Bezos “deserves to be shamed.”
- “Leo had the best reaction.” – Chelsea Handler [93:39]
Awards show chaos: Timothée Chalamet reportedly “blowing up the bathroom,” presenting logistical challenges.
On celebrities’ performances: “I love that she [Taylor Swift] just gives her money away to so many different people. How can you say anything negative about a person who does that?” – Chelsea Handler [90:44]

Chelsea’s Whistler Lifestyle & Drug Stories

Handler shares her dual life—workaholic in LA, “homeless” ski bum in Whistler with a house full of kids (not hers).
- “Kids like me because I’m not interested. … I want kids to have a person like me in their life to show them what’s possible.” – Chelsea Handler [100:51]
She reflects on learning to ski after an embarrassing double-black-diamond date with a Kennedy-adjacent ex (“I ignored the red flag for two years…”), and taking lessons with both male and female instructors.
Travel, “psychedelic conference” in Antarctica, and her distaste for ketamine.
Ayahuasca experience changed her relationship with her sister:
- “…This voice is talking to me… telling me I had to be nicer to my sister. … It was like an iPod shuffle of memories.” – Chelsea Handler [106:46]

High & Mighty Tour & Advice Podcast

Chelsea’s “High and Mighty Tour” begins in February, focusing on travel, drugs, family stories, and self-improvement.
Praises the liberating power of “editing” family for boundaries and happiness.
Her advice podcast “Dear Chelsea” (soon on Netflix) is about helping people take leaps and “get out of bad relationships,” with a favorite anecdote about quitting pot alongside a caller.

Notable Quotes

“People need to know you can cut people out of your family. Who gives a shit? You don’t have to say it’s forever.” – Chelsea Handler [109:51]
“I like to take drugs around the world and give them to people. … I feel like I’m healing people.” – Chelsea Handler [108:37]
On being direct: “You don’t have to be a cunt about it – you can just say something that’s hard to hear in a nice way.” – Chelsea Handler [118:35]
On Hollywood romance: “I use these award shows in the same way I use my TV: to hit on men I’m attracted to.” – Chelsea Handler on her attempts to pursue Ralph Fiennes [124:28]

Notable & Memorable Moments

Espresso tutorials and TikTok rabbit holes. [08:32–14:23]
Fran, Rhea, and Noah’s confusion over Billboard chart rules and music licensing. [59:37–68:18]
The Ashley Tisdale friend drama spiral showing the unpredictability of social media mob mentality. [25:44–38:47]
Chelsea’s anecdote about legitimately changing her life after ayahuasca (“iPod shuffle of memories”). [106:46]
Jane Fonda once sat Chelsea down to call out bad behavior—leading to a true friendship and personal growth. [118:44–120:37]

Interview Timestamps

[89:29] Chelsea joins the show: pop culture, Taylor Swift, and Critics Choice Awards
[91:41] Roasting celebrities; awards show nerves and tactics
[93:39] Best reactions, BTS logistics (Timothée Chalamet’s bathroom breaks)
[94:59] Oprah, mending impressions, and forgiveness
[99:44] Whistler, the “youth hostel” holiday house, and how Chelsea parents other people’s kids
[101:45] The skiing origin story, conquering black diamonds, and ex-flings as ski instructors
[104:09] Antarctica psychedelic boat trip, ketamine, ayahuasca, and “healing” with drugs
[108:34] High & Mighty Tour and advice for “editing” family
[112:35] Dear Chelsea podcast, call-in follow-ups, and advice philosophy
[119:44] Jane Fonda calls her out: the power of honest female friendship
[124:28] “Using” the Critics Choice Awards to hit on Ralph Fiennes
[125:51] On her past with 50 Cent, gambling in Vegas, and post-show rituals

Final Thoughts & Takeaways

January blues are universal—espresso and Dyson vacuums can help.
Adult friendship politics are as messy as high school; Ashley Tisdale’s story shows the internet is quick to judge.
Chelsea Handler is unabashedly herself, whether roasting A-listers or teaching listeners to set boundaries—her approach is equal parts vulnerable, irreverent, and empowering.
The pop culture world remains unpredictable and captivating, from music charts to award shows to the perennial mysteries of Shakespeare and literary adaptations.
If you need a good laugh, a sharp perspective, or candid life advice, Chelsea’s new tour and Netflix podcast are not to be missed.

Resources / Further Listening

Chelsea Handler’s High & Mighty Tour: ChelseaHandler.com
Dear Chelsea podcast (soon on Netflix)
Chicks in the Office YouTube, Spotify, Apple Podcasts

End of Summary
“January is the Sunday of the week. Some might think it’s the Monday, but in my brain, January is the Sunday…” – Fran [03:02]

Chelsea Handler Talks Roasting Leonardo DiCaprio & Critics Choice BTS, Her Favorite Drugs + More!

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Summary

Chicks in the Office: Chelsea Handler Talks Roasting Leonardo DiCaprio & Critics Choice BTS, Her Favorite Drugs + More!

Episode Overview

Key Discussion Points & Insights

1. Surviving the Post-Holiday January Blues

2. New Year's Epcot Revelations

3. Pop Culture News Corner

Ashley Tisdale’s ‘Toxic Mom’ Clan Drama

Real Housewives & Reality TV Updates

Book & Film Gossip: The Housemaid Sequel & Sydney Sweeney

4. Popcorner Hot Takes (Listener Calls & Culture Debates)

TV Spoiler Frustrations & Bachelorette Speculation

YouTube, Billboard, & the Future of Music Videos

Awards Show Hot Take: Should Repeat Acting Wins Be Allowed?

Shakespeare, ‘Hamnet’, and Taylor Swift Connections

FEATURE INTERVIEW: CHELSEA HANDLER

Critics Choice Awards BTS & Roasting the Stars

Chelsea’s Whistler Lifestyle & Drug Stories

High & Mighty Tour & Advice Podcast

Notable Quotes

Notable & Memorable Moments

Interview Timestamps

Final Thoughts & Takeaways

Resources / Further Listening

Summary

Chicks in the Office: Chelsea Handler Talks Roasting Leonardo DiCaprio & Critics Choice BTS, Her Favorite Drugs + More!

Episode Overview

Key Discussion Points & Insights

1. Surviving the Post-Holiday January Blues

2. New Year's Epcot Revelations

3. Pop Culture News Corner

Ashley Tisdale’s ‘Toxic Mom’ Clan Drama

Real Housewives & Reality TV Updates

Book & Film Gossip: The Housemaid Sequel & Sydney Sweeney

4. Popcorner Hot Takes (Listener Calls & Culture Debates)

TV Spoiler Frustrations & Bachelorette Speculation

YouTube, Billboard, & the Future of Music Videos

Awards Show Hot Take: Should Repeat Acting Wins Be Allowed?

Shakespeare, ‘Hamnet’, and Taylor Swift Connections

FEATURE INTERVIEW: CHELSEA HANDLER

Critics Choice Awards BTS & Roasting the Stars

Chelsea’s Whistler Lifestyle & Drug Stories

High & Mighty Tour & Advice Podcast

Notable Quotes

Notable & Memorable Moments

Interview Timestamps

Final Thoughts & Takeaways

Resources / Further Listening