The JTrain Podcast: "Dancing with the Stars Hilaria Baldwin Elimination!? with Anna Roisman – CHIT CHAT WEDNESDAY"

Host: Jared Freid
Guest: Anna Roisman
Date: October 15, 2025

Episode Overview

Jared Freid welcomes comedian, friend, and impersonation expert Anna Roisman to a lively "Chit Chat Wednesday." Together, they dive into Anna’s viral celebrity impressions—especially Hilaria Baldwin—discuss the nuances of pop culture fame and internet controversies, reminisce about 90s and early-2000s movie urban legends, and cap things off with playful improv games featuring Anna’s best character work. This episode is candid, comedic, and full of insider stories from the world of comedy and social media stardom.

Key Discussion Points & Insights

Childhood Memories, Movies, and Urban Legends

• Weather Talk, Wizard of Oz, and Conspiracy Theories
  • Jared and Anna banter about their locations—Jared in stormy Delray Beach, Anna in sunny Williamsburg (Brooklyn)—and segue into “The Wizard of Oz.”
  • Anna recalls the urban legend of a supposed body hanging in the background of a scene (“My only memory of The Wizard of Oz is that someone died on set... My brother and I would sit there and we would, like, watch it in slow motion and be like, that's the body. I see the ghost.” – Anna, 03:27).
  • They further reference similar legends from “Three Men and a Baby,” pondering if movies like that could ever be remade today.

Online Identity & 90s Nostalgia

• Remaking "You've Got Mail"
  • Discussion on how online dating and anonymity have changed, with Anna and Jared reflecting on the now-bizarre idea of not knowing who one is talking to online.
  • Anna admits to catfishing in AOL chat rooms as a kid:
    • “Yeah, I loved catfishing in chat rooms. That was like a skill I had as a kid. I'd be like, I'm a 55 year old dad from Delray beach looking for a nice young lady. And I was like, this is awesome.” (08:10)
  • Jared jokes this is how Anna’s impersonation skills really started.

Anna's Celebrity Impersonations & Industry Anecdotes

Hilaria Baldwin: Inspiration, Viral Fame, and Awkward Encounters

• Anna’s impressions of Hilaria Baldwin gained viral traction:
  • “I just was obsessed with the story when that broke out, because I think it was friends of hers from high school, from Boston, who are like, hold on. Like, she, her name was Hillary. Like, we went to high school with her.” (14:41)
• Jared dives into why Hilaria’s story is so memeworthy and exasperating, especially for “uninteresting” suburbanites.
  • “If you live in, like a land of like nuance and context... you go, wait a minute. She's 41 and from Weston, Massachusetts, and her name is Hillary. And this was all like a maniacal plan to get riches...” (12:16)
• Their online relationship was rocky: Anna recounts attempts to collaborate, mixed responses, and how Hilaria’s “team” was hyper-controlling about content:
  • “...I pitched these ideas, which really made her look better. And I look like the... And anyway, I didn't. They were like, we're not going to speak on camera. We don't want to do anything with the accent.” (24:00)
  • After collaborating, Anna says: “Her haters came for me as if... I, like, voted for Trump. Like, it was the weirdest thing ever.” (24:56)

The Dancing with the Stars “Unfair Competition” Anecdote

• Anna shares a memorable moment meeting Hilaria Baldwin, who claimed she was too good for DWTS:
  • Quote: “She looks at me and goes, you know, I am a trained ballroom dancer, so if I went on Dancing with the Stars, it would be an unfair competition.” (25:34)
  • Jared and Anna joke about the outsized confidence and meme-ability of Hilaria (“It just wouldn't be fair.” – Anna imitating Hilaria, 27:40).
  • Hilaria was then quickly eliminated (week three) from the show—delighting the comedians.

Other Notable Impressions:

• Kris Jenner:
  • Anna and Jared analyze her tick (the infectious laugh):
    • “You saw something that was in plain sight that no one saw. That laugh.” (19:15)
    • “If you watch the show, too, which I love... she can laugh about it. And I hope I get to be that rich where no matter what happens, right? Just laugh, because my day is going to be fine...” – Anna, 19:24).
• Bethenny Frankel:
  • Anna recounts meeting Bethenny, who immediately demanded an impression on-camera, “like a stage mom.” She reflects on Bethenny’s relentless TikTok output and her “dating concept” scheme.

Loving & Meeting the People You Impersonate

• Jared and Anna discuss the unexpected dynamics of meeting the source of an impersonation:
  • “I love it... my dream is to meet Kris Jenner.” – Anna, 18:45
  • “The best impressions are when... you have one tick that you repeat over and over again to remind.” – Jared, 19:15

Sex and the City: Meeting "Steve" and Character Analysis

• Anna met "Steve" (David Eigenberg), describing him as “the nicest”—bringing character impressions into the real world.

Memorable Quotes & Moments

On Why Making Fun of Hilaria Baldwin Is Irresistible:

• “Because there's social currency in the year 2025 when you say I have a very interesting background.” – Jared, 12:42

On the Viral Anna/Hilaria Impersonation:

• “I didn't know it blew up until like the LA Times was like, tiktoker Anna Roisman is commenting on Lori Baldwin. I was like, oh my God. LA Times called me a tik tocker.” – Anna, 15:29

On TikTok's Demand for Repetition:

• “If one thing works, there is the temptation to just keep beating that drum. But that's not what we're here for.” – Jared, 16:12

On Hilaria’s DWTS Confidence:

• “...if I went on Dancing with the Stars, it would be an unfair competition.” – Anna as Hilaria, 25:34
• “That's going to be my dreams. And I'm going to think of her going, ‘It just wouldn't be fair. It just wouldn't be fair.’” – Jared, 27:31

On Meeting Bethenny Frankel:

• “And she, like a stage mom, pulled out her phone and goes, go, do me. Go, go.” – Anna, 32:08

Notable Segments & Timestamps

Opening Banter

• [00:00–03:59] – Opening chat, weather talk, NYC/Florida contrast, Wizard of Oz, childhood movie conspiracy memories.

Pop Culture, Impersonations, & Internet Celebrity

• [11:31–14:41] – Anna discusses awkward impersonation moments, especially with Hilaria Baldwin.
• [14:33–16:46] – How Anna’s Hilaria impression started, its viral reception, and details on the impersonation’s impact.
• [18:42–20:22] – Anna’s celebrity social media encounters and the anatomy of a good impression (focus: Kris Jenner’s laugh).
• [22:52–27:40] – Anna details the attempt to collaborate with Hilaria, the Dancing with the Stars anecdote, internet hate, and fan backlash.
• [29:09–31:38] – Reflections on meeting real TV characters (Steve from Sex and the City), Hollywood’s oddities, and performer survival in the modern landscape.

Impressions Games & Skits

• [33:23–39:37] – Improv games featuring Anna’s impressions:
  • Sex and the City’s Miranda & Steve deal with infidelity
  • Kris Jenner pitches Kim Kardashian a (ridiculous) vibrator brand deal
  • Bethenny Frankel tries to return half-eaten chicken salad at a market

Closing Thoughts

• [39:53–41:12] – More Bethenny, TikTok culture, and shout-outs to Anna’s social media.

The JTrain Comedy Vibe: Original Tone

• The episode is playful, sarcastic, sometimes self-deprecating, with plenty of “inside baseball” references to comedy, the internet, and the weirdness of celebrity culture.
• Jared is blunt, gossipy, and both lovingly & exasperatingly fixated on pop culture absurdities.
• Anna matches him in energy, offering both sharp takes and extremely funny impressions throughout.

Takeaways for Listeners

• Anna’s celebrity impersonations are both a creative outlet and a minefield, frequently crossing paths with the real people she parodies—with mixed and often humorous results.
• The internet’s reaction to viral content is unpredictable and can unite both fervent fans and haters.
• The lines between content, performance, and “real life” blur in the age of TikTok and social media fame.
• Celebrity self-seriousness is often the best fuel for parody and internet memes, as seen with Hilaria Baldwin’s self-mythologizing and overconfidence.

Follow & See More

• Anna Roisman: @AnnaRoisman on Instagram/TikTok — find her impressions and live shows.
• Jared Freid: For tour info, see JaredFreid.com
• Both will be performing live in Washington, D.C. on October 23, 2025.