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Tommy Montgomery is an NYC-based Actor, Comedian, and Musician. Off-Broadway: Jim/Andy in The Office! A Musical Parody (The Theater Center). Comedy: Characters Welcome (UCB); Dogs in Strollers, Babies on Leashes (The PIT); Electric Panini (BoogieManja); Foolharmonic (Peoples' Sketch Revues); Main Character Energy (Second City NYC); Ninjas Assemble (UCB); The Character Annex (The PIT); Bootleggers 'N Gangsters (Whiskey Stories), and more. His solo sketch show Dogs In Strollers, Babies on Leashes has played The PIT Mainstage twice and returns for a third time in October 2025. Tommy is an experienced children's entertainer and musician. He acts in interactive plays for children with disabilities (Only Make Believe NYC), he acts and plays guitar in musical puppet shows (Shadow Box Theatre NYC), he plays guitar for music therapy sessions for kids (Creative Speech Therapy NYC), he performed as the mascot "Blaze" for the 2024 ICC T20 Cricket World Cup. He grew up in the Chicago area and has his BFA in Acting from Syracuse University. IG: @tommy_montgo

COMEDY VIDEOS

Mario Has To Do Whatever You Tell Him
05:40
MICKEY MOUSE TRAPHOUSE (SOLOCOM)
03:42
DAVE MATTHEWS BAND PARODY (PSR)
04:45
Jim/Andy in The Office! A Musical Parody
01:51
A Rapper With A Lot of Food Allergies
04:48
"Ain't Nobody Here But Us Chickens"
03:37
Biden Press Conference
04:38
The Electoral College
05:08

UPDATES

Updates

Solo Comedy Show

PIT SOLOCOMNYC'25

On April 11th, Tommy debuted his solo show "Dogs in Strollers, Babies on Leashes" as a part of SOLOCOM Fest at The PIT. Through impressions, he brought cartoon characters to life in this "children's show for drunk adults".

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FoolHarmonic 4/4

PSR Musical @ The PIT

On April 4th, Tommy performed in his debut show with "FoolHarmonic", the PIT's Musical team as a part of the house team series Peoples Sketch Revues. Watch his Dave Matthews Band Parody sketch here.

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Mascot Handler

New York Mets

Beginning in March, Tommy joined the New York Mets mascot team as a handler for Mr. and Mrs. Met.

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Main Character Energy

Second City NYC

In February 2025, Tommy returned to the Second City Blackbox in Main Character Energy, performing original character work.

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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.

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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".

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Electric Panini 5/14

BoogieManja @ The PIT

On May 14th, Tommy performs in his third show with "Electric Panini", a sketch team with BoogieManja Sketch Comedy Collective. Electric Panini has monthly performances at the PIT. For tickets, click here.

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Musician

Creative Speech Therapy

In March, Tommy began playing guitar for pediatric music therapy sessions for kids with Creative Speech Therapy.

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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.

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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.

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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.

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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.

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FoolHarmonic 5/9

PSR Musical @ The PIT

On May 9th, Tommy performs in his second show with "FoolHarmonic", the PIT's Musical team as a part of the house team series Peoples Sketch Revues. For tickets, click here.

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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".

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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.

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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.

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Main Character Energy

Second City NYC

In August 2024, Tommy made his Second City NYC debut in Main Character Energy, performing original character work.

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Electric Panini 4/16

BoogieManja @ The PIT

On April 16th, Tommy performed in his second show with "Electric Panini", a sketch team with BoogieManja Sketch Comedy Collective. Pictured is Tommy in "Vasectomy Disco".

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Characters Welcome

Livestream 3/26

On March 26th, Tommy performed character comedy on the Characters Welcome Livestream hosted by Eric Feurer and Justin Tyler.

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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.

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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. 

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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".

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Tommy as Jim/Andy in The Office! A Musical Parody Off-Broadway

Tommy is Jim!
Masking Tape 2
Masking Tape 2

Tommy played Jim/Andy in the Off-Broadway cast of The Office! A Musical Parody. He played his 250th and final performance on April 30th, 2023. Watch his work in the video above.

 

After being cast in February 2022 as a swing, Tommy made his Off-Broadway debut on March 24th and was promoted to the role of Jim/Andy in June 2022.

On May 19th, 2022, Jenna Fischer and Angela Kinsey (Pam and Angela in the original sitcom) surprised the cast and saw the show while Tommy was swinging on for Toby/Creed. Read the People Magazine article about Jenna and Angela's surprise visit.

Tommy celebrated his 100th show with The Office! in October 2022, and both his 200th show and 1-year anniversary in February 2023.

Tommy's Final Bow
4/30/2023

Jim and Pam

The Office
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