EPISODE · Apr 8, 2025 · 55 MIN
Tommy Brennan: Say His Therapist's Name (It's Cheryl)
from Xanyland: Comedians on the Couch · host Alicia Racine Fink
Tommy Brennan has been in therapy for six years. He preps for each session like a podcast, journals throughout the week, and once bombed so badly in front of 30 Brooklyn comedians that it was, somehow, exactly what he needed. In this episode, Alicia and Tommy get into the mechanics of actually doing therapy right — the prep, the trust, the willingness to follow where it leads. They also cover: the LinkedIn-to-comedy pipeline, why big families produce performers, and what it means to put a room on a pedestal for years. Plus: Alicia confesses to developing real feelings for a professor who turned out to be her own therapist's husband.For comedians, creatives, and anyone who's been recommending therapy for years without actually going.
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What this episode covers
In this episode of Xanyland, comic Tommy Brennan brings the laughs and the feels as he opens up about therapy, bombing, and building a name in comedy without losing his mind—or his stylistic integrity. From the raw chaos of bombing a set to the existential dread of “How do I look on stage?”—Tommy and Alicia go deep on what it means to find your voice when you're one of eight siblings and the only one doing stand-up. They unpack why choir is basically crack for young boys, why a “dream job” at LinkedIn can be a creative death sentence, and why therapy only works if you actually do it right. Alicia confesses to falling in love with her therapist’s husband (without knowing it), and Tommy gives a loud and proud thank-you to his therapist, Cheryl—who maybe shouldn’t come to his shows. Whether you’re a comic, a creative, or just curious about how therapy and self-presentation collide, this episode is for you. Listen now on Spotify, YouTube, or wherever you get your T.
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Tommy Brennan: Say His Therapist's Name (It's Cheryl)
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