Tommy Montgomery is an NYC-based Actor, Comedian, and Musician, best known for his year-long Off-Broadway run as Jim/Andy in The Office! A Musical Parody. He is a current member of sketch teams Electric Panini (BoogieManja) and Peoples Sketch Revues (PIT), and has performed in various comedy shows around the city such as Main Character Energy (Second City Blackbox) and The Character Annex (PIT). His solo sketch show “Dogs In Strollers, Babies on Leashes" debuts at The PIT’s SOLOCOM Fest in April. Tommy was the mascot for the 2024 Cricket World Cup, and has extensive children’s theatre credits with Only Make Believe, Syracuse Stage, and Shadow Box Theatre. He plays guitar for Shadow Box Theatre’s musical puppet shows, and has played saxophone and guitar for bands at Arlene’s Grocery and Brooklyn Music Kitchen. BFA Acting: Syracuse University. IG: @tommy_montgo
Outside his creative endeavors, Tommy is a Kayak Guide and Instructor at Manhattan Kayak Company. With 6 years of guiding experience and an instructor certification from the American Canoe Association, he leads tours along the Hudson River and teaches classes to beginners and advanced paddlers alike. Hometown: The Chicago suburb of Skokie, Illinois Career Inspirations: Jack Black, The Lonely Island, Rachel Bloom, Ed Helms, Donald Glover, Jason Sudeikis Favorite TV: Ted Lasso, New Girl, Crazy Ex-Girlfriend, Michael Schur sitcoms (The Office, Parks & Rec, The Good Place), I Think You Should Leave Interests: Dialects, Musical Comedy, Satire
UPDATES
Solo Show 4/11
PIT SOLOCOMNYC'25
On April 11th, Tommy performs his solo show "Dogs in Strollers, Babies on Leashes" as a part of SOLOCOM Fest at The PIT. He brings cartoon characters to life in this "children's show for drunk adults". For tickets, click here.
Characters Welcome
Livestream 3/26
On March 26th, Tommy performed character comedy on the Characters Welcome Livestream hosted by Eric Feurer and Justin Tyler.
Main Character Energy
Second City NYC
In February 2025, Tommy returned to the Second City Blackbox in Main Character Energy, performing original character work.
Chicago Marathon
Finisher
In October 2024, Tommy ran The Bank of America Chicago Marathon! He finished 26.2 miles in 3:28:29 at an average pace of 7:55 per mile! This was his first marathon and he ran it in his hometown of Chicago.
Brooklyn Music Kitchen
Saint Street Band
In July 2024, Tommy played saxophone and guitar for Saint Street Band during their featured half-hour set at Brooklyn Music Kitchen hosted by Mike Geffner's Inspired Word. Click here to watch him play lead guitar on a cover of "Misery Business".
FoolHarmonic 4/4
PSR Musical @ The PIT
On April 4th, Tommy performs in his debut show with "FoolHarmonic", the PIT's Musical team as a part of the house team series Peoples Sketch Revues. For tickets, click here.
BoogieManja Sketch
New Team
In February 2025, Tommy joined the BoogieManja Sketch Comedy Collective's house team "Electric Paninil" as an actor. He'll be performing in a monthly sketch comedy show at The PIT. For tickets, click here.
Arlene's Grocery
Rita Castagna's Band
In February 2025, Tommy played saxophone and guitar for Rita Castagna's band at a packed-house Arlene's Grocery in Manhattan.
The Floor Season 2
Contestant
Tommy competed on Season 2 of the trivia game show THE FLOOR, hosted by Rob Lowe on FOX. Watch S2E5 "High Risk, High Reward?" to see his nail-biter of a battle naming ocean animals.
T20 Cricket World Cup
Mascot
In June 2024, Tommy performed as the Mascot "Blaze" for the ICC Men's T20 Cricket World Cup matches hosted in New York. Crowds travelled from across the globe to watch cricket and take selfies with Blaze. Click here for a video.
Electric Panini 3/19
BoogieManja @ The PIT
On March 19th, Tommy performed in his debut show with "Electric Panini", a sketch team with BoogieManja Sketch Comedy Collective. Pictured is Tommy as Byra Tanks, host of "America's Next Top Bear".
PSR Musical House Team
Peoples Improv Theater
In January 2025, Tommy joined the Peoples Sketch Revue house team at The PIT as a writer and performer. He'll be producing musical sketch comedy in a monthly show. For tickets, click here.
Haus of Characters
Brooklyn Art Haus
In January 2025, Tommy performed original character work at Haus of Characters, a night of character comedy at Brooklyn Art Haus.
Main Character Energy
Second City NYC
In August 2024, Tommy made his Second City NYC debut in Main Character Energy, performing original character work.
Electric Panini 4/16
BoogieManja @ The PIT
On April 16th, Tommy performs in his second show with "Electric Panini", a sketch team with BoogieManja Sketch Comedy Collective. Electric Panini has monthly performances at the PIT. For tickets, click here.
Only Make Believe
2025 Acting Company
In December 2024, Tommy joined the NYC Acting Company at Only Make Believe, a non-profit arts organization that creates and performs interactive theatre for children in hospitals, care facilities, and special education programs.
Shadow Box Theatre
Actor-Musician
Tommy completed his third year playing guitar for children's musical puppet shows with The Shadow Box Theatre. He tours NYC boroughs for ages 3-8 with the shows Tobias Turkey, Lumpy Bumpy Pumpkin, Big Annie, and Little is Big.
The Character Annex
Peoples Improv Theater
In July 2024, Tommy performed his original musical character "G Freezy", a rapper with a lot of food allergies, in The Character Annex at The PIT. Click here to watch "Let's Get This Bread".
