The Commercial Break – TCB Infomercial: Natasha Leggero

Episode Date: October 22, 2024
Hosts: Bryan Green & Krissy (Kristen Joy) Hoadley
Special Guest: Natasha Leggero

Overview of Episode

This episode of The Commercial Break’s “Infomercial” series features comedian, actress, and podcaster Natasha Leggero. Bryan and Krissy dive into Natasha’s work on the new show Are You Smarter Than a Celebrity? (Prime Video), her long-running podcast Endless Honeymoon, her unique comedic takes on marriage and motherhood, and the absurdities of modern pop culture parenting. As always, the conversation is peppered with hilarious tangents, playful self-deprecation, and the hosts bonding over their mutual admiration for Natasha’s humor and honesty.

Key Discussion Points & Insights

1. Are You Smarter Than a Celebrity? and Working with Travis Kelce

[20:18 – 29:58]

• Natasha describes her experience as a celebrity participant on the new trivia show hosted by NFL star Travis Kelce, modeled after Are You Smarter Than a Fifth Grader?

  • The show features celebrities (including comedians like Ron Funches, Nicole Byer, Lilly Singh) as “lifelines” for contestants.
  • Natasha admits that “elementary school” questions can be alarmingly difficult, especially in math and science.

  “It was really traumatizing because you start to—some of the math stuff, I’m like, I don’t, I don’t know even where I would begin.” (Natasha, 21:12)

  • She reflects on the pressure of possibly being the reason a contestant loses prize money.

  “Honestly, it’s the worst part about the show…I was on $100,000 Pyramid and my contestant started crying because I did not know any of the answers.” (Natasha, 29:02)

• Travis Kelce’s performance as a host earned unanimous praise:

  “He freaking killed it…he’s good at football, right? He’s like one of the good ones…and then he came in and he was so disarming. He really took the job seriously, but then he was also being fun and funny and not taking himself too seriously.” (Natasha, 26:41)

• Natasha hints at a Taylor Swift set visit but keeps details light due to NDA/spoilers.

  “There actually was a Tay Tay sighting…there was some hubbub that she was there—but I don't want to give too much away.” (Natasha, 28:00)

2. Marriage, Hobbies, and Roasting Your Partner

[14:39 – 19:21]

• Natasha jokes about her husband Moshe Kasher’s excessive hobbies (DJing, surfing, Burning Man), teasing how men pick up hobbies to avoid responsibility.

  “First of all, too many hobbies. Why does he have—why do men have so many hobbies?” (Natasha, 14:59)

• She gleefully roasts his midlife DJ ambitions and her tactical insistence that he wear a “surfing helmet” for safety.

  “I make him wear a helmet. Actually, I told Tony Hawk that…and they were just making fun of my husband so hard.” (Natasha, 17:47)

• The conversation expands to the shift in risk tolerance and “tolerance in marriage” as people age:

  “Estrogen is what makes you tolerant, so all your tolerance is just getting sucked out of you…that’s why the podcast has been so great, because I can just start bringing up all my grievances.” (Natasha, 19:21)

3. Parenting & Technology in the 2020s

[35:03 – 45:42]

• The group discusses the challenges of raising children post-iPhone era, especially around screen time and social media:

  • Natasha restricts her daughter’s access to iPads and emphasizes modeling good phone habits for her child and spouse.

  “It is a weird thing to be like, ‘no iPad, no social media, no technology,’ and then we’re just…completely addicted to our phones.” (Natasha, 37:21)

  • They commiserate over the challenges of getting children to open up after school and the overwhelming influence of YouTube and internet culture on young kids’ aspirations.

  “My daughter came home and she said…the teacher asked all the kids what they wanted to be. And she said every boy in the class said they wanted to be a YouTuber.” (Natasha, 35:38)

• Screen time “rules and lapses”:

  • The hosts share their mixed success enforcing “no screens at dinner,” and acknowledge that sometimes TV is the lesser evil (“we also tend to default to the television…because it gives us a break” [Bryan, 41:00]).

• On the modern politics of parenting advice and the anxiety of Instagram parenting:

  “Every time I would log on to Instagram, it was someone telling me I was doing everything wrong…so I just needed to have a little bit of distance and boundaries with that.” (Natasha, 44:28)

• Notable moment: Natasha’s family uses the “Rose, Bud, Thorn” tradition as a conversation starter at dinner to keep communication open and screens away.

  “You go around the room, say your rose—the best part of your day, bud—something you’re looking forward to, and thorn—the worst part…and that usually gets you through dessert…” (Natasha, 41:56)

4. Comedy Career Highlights

[46:52 – 48:56]

• Bryan and Krissy reminisce about Natasha’s cult favorite show Another Period and her origins on MTV’s bizarre reality spoof That 70s House (which she confirms is legally/illegally on YouTube):

  “If you want a little snapshot of what 2005 was like…It’s kind of ahead of its time, to be honest…these teenagers have to live in this house like it’s the 70s.” (Natasha, 47:38)

5. The Endless Honeymoon Podcast & Relationship Advice

[48:56 – 49:55]

• Natasha explains that Endless Honeymoon started as a podcast before their Netflix special, and how it’s become a space to comedically “give advice” to young couples and share marriage stories—especially during the pandemic.

  “My husband’s been sober for almost, I think, thirty years…and I’ve had, you know, maybe ten serious relationships. So I think together, we’ve been able to—and it’s fun also seeing a lot of young people calling in…” (Natasha, 48:56)

Notable Quotes & Memorable Moments

• On Jeff Bezos/Musk-level wealth and loneliness:

  “Imagine you made $35 million a minute and still no woman wanted to [date] you. That is what we’re dealing with.”
  —Natasha Leggero ([00:00])

• On DJ 'hobbies' for 40-something men:

  “You’re 44. Why is there a beat dropping? It’s noon.”
  —Natasha ([15:19])

• On losing at TV game shows:

  “My contestant started crying because I did not know any of the answers. I felt so bad. It doesn’t feel good, you know.”
  —Natasha ([29:02])

• On parental advice Instagrams:

  “Every time I would log on…it was someone telling me I was doing everything wrong…and I just needed to have a little bit of distance and boundaries with that.”
  —Natasha ([44:28])

Important Timestamps

• 00:00 Natasha on tech billionaires, loneliness, and the gender divide
• 01:36 Announcement of TCB’s charity episodes for the holidays
• 03:02 Natasha’s comedy career—Chelsea Lately, Another Period, That 70s House
• 13:21 Natasha joins the conversation; discussion of her Hermes wallpaper and home podcast setup
• 14:39 – 19:21 Marriage, roasting husbands, men and their “avoidant” hobbies
• 20:18 – 29:58 Are You Smarter Than a Celebrity? tales, working with Travis Kelce, game show pressures
• 35:03 – 45:42 Parenting in the 2020s: phones, screens, kids’ aspirations, and social media anxieties
• 46:52 – 48:56 Natasha’s comedy origins and revisiting That 70s House
• 48:56 – 49:55 Endless Honeymoon: podcasting, marriage advice, pandemic shifts

Episode Tone & Takeaways

• The discussion is fast-paced, irreverent, and self-aware, with the guests and hosts unafraid to mock themselves, modern life, and even the structure of their own show.
• Natasha’s sharp observational wit shines, especially as she riffs on marriage, parenting, and the surreal nature of celebrity game shows.
• Parenting and childhood screen time become central themes, revealing generational differences and the hosts’/guest’s efforts to stay grounded in a world of “forever elsewhere” phone culture.
• Travis Kelce (and by extension, Taylor Swift) are warmly praised, with Natasha calling out Travis’s disarming charm and “positive vibes” as a key factor in the show’s energy.
• The episode closes with hosts reaffirming their admiration for Natasha and highlighting her body of work—including recent and classic projects.

For New Listeners:

You’ll come away from this episode with a sense of Natasha Leggero as an open, introspective, and riotously funny guest, as well as a window into the collaborative, chaotic, and affectionate TCB universe. Whether you’re here for parenting laughs, pop culture, absurd tangents, or behind-the-scenes glimpses of showbiz, this Infomercial delivers.

Listen for:

• Natasha on husband-mocking (“It’s like the opposite of me and my husband, where I make fun of him whenever we’re in public.” [28:21])
• Painful and hilarious reality of being a game show lifeline
• Candid takes on parenting in a hyper-digital age
• Why Travis Kelce has “the it factor” and could be a host for ages
• Drop-in wisdom: “Bribery is a form of parenting.” (Bryan, 44:27)

Natasha Leggero’s Current Projects

• Are You Smarter Than a Celebrity? – streaming now on Amazon Prime
• Endless Honeymoon Podcast – available on Dear Media
• Check out her stand-up special Endless Honeymoon (Netflix)
• Previous work: Another Period (Paramount+), That 70s House (YouTube)

[End of Summary]