Tommy Montgomery
COMEDIAN
Hi, I’m Tommy Montgomery! I’m an NYC-based actor, comedian, and writer. Off-Broadway: Jim/Andy in The Office! A Musical Parody. In 2025, I wrote and acted for sketch teams with BoogieManja and Peoples Sketch Revues (house team at The PIT). NYC sketch comedy: UCB, Characters Welcome, BoogieManja, Peoples Sketch Revues, NYC SketchFest, Second City NYC, The PIT, Magnet Theater, BCC, Whiskey Stories, Caveat, The Rat. Training: BFA Acting from Syracuse University, Shakespeare’s Globe, Upright Citizens Brigade NY (character and sketch). I host and produce the character show Mickey Mouse Traphouse in which comedians parody your favorite childhood characters, and my solo sketch show played The PIT’s mainstage three times in 2025. I am a skilled impressionist and multi-instrumentalist, and I gravitate toward writing musical comedy and characters with distinct voices and physicalities. I play saxophone and guitar, am allergic to peanuts and gluten, and am afraid of heights.
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Follow me on Instagram at @tommy_montgo (10K) for more sketch content!
"His attempts at singing go awry over and over, interrupted by his groans, wheezes, moans, and nervous laughter."
- Upworthy
In my solo sketch hour in July 2025 at The Peoples Improv Theater, I attempted to sing while wearing a period simulator operated live onstage by my fiancée, Talia. The video has surpassed 19 million views on Instagram, and Talia and I were interviewed by Upworthy magazine about how the experiment can help men be more empathetic to the experiences of women and people with uteruses. Watch the video and read the article below.