Dear Chelsea: "Fanilow to Ambassilow with Michael Urie"

Podcast: Dear Chelsea (iHeartPodcasts)
Host: Chelsea Handler (with co-host Katherine Law)
Guest: Michael Urie
Air Date: August 21, 2025

Episode Overview

This week’s episode sees comedian Chelsea Handler welcome acclaimed actor Michael Urie (of “Shrinking,” “Ugly Betty,” and Broadway’s “Oh, Mary!”) for a lively, candid exploration of fame, fandom, romance, and personal growth. Mixing humor with heartfelt advice, they discuss Michael’s love for Barry Manilow, the realities of acting on stage and screen, career burnout, and personal relationships. As always, Chelsea and Katherine field listener calls, tackling thorny family dynamics, relationship dilemmas, and friendship boundaries, with Michael lending his unique perspective as both a Broadway star and a compassionate guest.

Key Discussion Points & Insights

1. Michael Urie’s Emmy Nomination & Career Journey

• Celebrating the Nomination:
  • Michael shares the excitement and disbelief at his first Emmy nod for “Shrinking.”
    • “This amazing world of Emmys is so new and exciting and crazy, and I still don't really believe it.” (06:33)
• Text Exchanges with Harrison Ford:
  • Michael details getting congratulations from co-star Harrison Ford, highlighting their playful camaraderie.
    • “I just texted him, dude. And he wrote back the same thing, 'dude.'” (07:35)
• On Becoming a Fanilow (Barry Manilow Superfan):
  • Michael talks about how he became not just a “Fanilow,” but an “Ambassilow,” introducing friends to Barry’s music and spirit, reflecting on how Manilow’s music resonated during his personal journey coming out.
    • “I make virgins Fanilows... I was very melancholy because I felt like I belonged in New York... and there was a new light FM station... playing a lot of Barry Manilow... it was really speaking to me that summer.” (09:26)
• Meeting Barry Manilow:
  • Michael describes meeting his idol, keeping his cool, and eventually forming a friendly relationship with Manilow—who’s even attended Michael’s shows. He admires Manilow’s ongoing commitment to performing well into his 80s.

2. Behind the Scenes of Broadway and TV

• Differences Between Theater and TV:
  • Michael relishes live theater’s immediacy and communal energy, compared to the more compartmentalized nature of film and TV.
    • “When you start a play at 7:30 at night for this group of 900 people and you finish it together, it's so special... It's really thrilling because I always get kind of emotional about it when I'm rehearsing a play.” (21:00)
• The Physical and Mental Demands:
  • He explains the need to structure his entire day around performance—even for shorter plays, and especially when doing double shows in a single night.
• Chelsea on Burnout and Returning to Standup:
  • Handler shares her own story of industry burnout, taking a six-year hiatus from standup and coming back with a better sense of purpose and presence.
    • “I liked getting off more than I liked being on stage... That's when I feel like I lost my... I had to recalibrate and come back and actually be so present...” (22:20)

3. Celebrity Perks and Fandom

• Chelsea on the Practical Benefits of Fame:
  • She jokes about using fame to meet heroes and “skip the line” at doctor’s offices.
    • “What else is fame for other than to meet your heroes?” (11:30)
    • “Doctors want celebrity clients... They won’t leave you in the waiting room.” (11:54)

4. Experimenting with Medical Marijuana

• Michael’s Pre-Acting Job as a Medical Marijuana Test Subject:
  • He recounts answering a Village Voice ad for drug trials, being given varying strengths of marijuana or placebo before doing cognitive tests in a hospital setting.
    • “I would go into a hospital and I would sit in a hospital room... One time I got just high as fuck.” (28:28)
  • Chelsea expresses envy and fascination with the setup, joking about her own love of hospitals and being waited on.
    • “I love hospitals. I love being taken care of. I love when people are tending to me in a medical way.” (29:35)
• Cognition and Cannabis:
  • Michael discusses how being high may have actually helped him memorize lines for shows.
    • “I will do it high. I will learn it high... then, like, when I go back to it later sober, it's there.” (31:57)

Listener Advice Segment

1. Maid of Honor Dilemma: Estranged Family Ties

• Email from Mandy: Torn about being maid of honor at her sister’s wedding due to long-standing family estrangement.
• Chelsea’s Advice:
  • “I think you have to go to your sister's wedding... You can fly in the night before if you want... follow through is kind of like 90% of life.” (39:01)
• Michael’s Advice:
  • “Lying is so dangerous because the truth is always easier to remember.” (41:03)
  • Both stress follow-through, honesty, and keeping commitments—even if it means careful boundary-setting for self-preservation.

2. Cheating in a Sexless Marriage

• Call from Mitchell: Married for five years, together ten, never had sex with his husband, started cheating to meet unmet needs, now seeking separation and feeling immense guilt.
• Chelsea:
  • “Stop self immolating... Your actions are circumstantial. You have to flip the script... To be in a nonsexual marriage for as many years as you were—that's not fun for you, and I'm sure it's not fun for your partner.” (44:36)
  • Suggests he pursue therapy with his husband to honestly and gently end the relationship and focus on co-parenting their niece and nephews.
• Michael:
  • “You're not a bad person.”
  • “We don't have to subscribe to heteronormative ways of monogamy...” (45:45)
  • Encourages honest and direct communication, and forgiving oneself. Recognizes the confusion/pain people in non-sexual relationships experience and the complex interplay of sexuality, identity, and expectation.
• Katherine:
  • “You don't need forgiveness from him, you just need to forgive yourself.” (52:01)

3. Friend’s Toxic Partner and Truth-Telling

• Call from Emily: Dislikes her husband’s best friend’s girlfriend, who’s lied about having cancer and displays attention-seeking behavior, even as her boyfriend now faces leukemia.
• Chelsea’s Guidance:
  • “It’s almost more important that her boyfriend know about her instead of her. She’s not gonna change because she’s got some problems, obviously.” (58:12)
  • Encourages Emily to talk directly to the friend (the boyfriend), possibly using examples of the girlfriend’s behavior to help him see the truth.
• Michael:
  • Supports honest, compassionate intervention.
• Katherine:
  • Raises issue of how to set boundaries with problematic friends’ partners.

Notable Quotes & Memorable Moments

• On meeting Barry Manilow:
  • Michael: “I played it cool. I have to say, I did play it pretty cool.... He couldn't have been cooler. He was so chill and so nice, and I don't know, he didn't really know who I was then. But I've been about, you know, like, 20 times since then. So now he does.” (12:33)
• Chelsea on performer longevity:
  • “There must be stuff you can take that just keeps you young. I mean, I know there is because I'm fucking taking it.” (13:28)
• On honesty vs. confrontation:
  • Michael: “Honesty doesn't have to be a confrontation. It can be like, you know, I have to tell you something... that's a friend. That's not a confrontation.” (68:26)
• Chelsea on self-care and boundaries:
  • “Always get a car.” (42:25)
• Chelsea, closing words:
  • “The world’s gonna end, like, any minute, so you better get out there and have a fucking good time. Enjoy your life. Please, everyone, listen. Enjoy your life.” (55:28)

Timestamps for Key Segments

• Chelsea’s Life Update & Guest Intros: 02:37–05:00
• Michael Urie joins/Emmy talk: 05:00–09:26
• Barry Manilow fandom, coming out, meeting heroes: 09:26–14:34
• On Broadway and performing live vs. TV: 19:44–22:20
• Chelsea discusses standup burnout and return: 22:20–24:10
• Medical marijuana trial stories: 27:25–32:29
• Listener Email: Maid of Honor & Family Estrangement: 37:36–42:27
• Caller Mitchell: Sexless Marriage & Separation: 42:36–55:56
• Caller Emily: Friend’s Toxic Girlfriend: 58:03–63:41
• Wrap up with Michael Urie: 68:00–69:39

Tone & Flow

Candid, comedic, sometimes irreverent but always supportive, the episode flows with quick-witted banter, vulnerable revelations, and direct, actionable advice. Chelsea’s signature mix of tough love and empathy blends perfectly with Michael’s earnestness and humor, making this episode both heartwarming and genuinely insightful.

Summary

This episode of Dear Chelsea perfectly showcases the show’s unique blend of celebrity chat and sharp life advice. Michael Urie’s presence brings both high-wattage charm and honesty as he reflects on his career, personal growth, and the power of fandom. The advice segments are deeply empathetic, especially regarding relationship difficulties and setting personal boundaries, with Chelsea and Michael offering both validation and practical steps forward for listeners in tricky spots. The entire episode is an engaging mix of laughter, truth-telling, and encouragement to choose honesty and self-worth.