Jackie Flynn

August 1, 2026

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Jackie Flynn is an actor and comedian with prominent standup

appearances, as well as extensive film credits to his name. Jackie

has emerged as one of the funniest and most talked about

comedians to come out of Boston, joining the ranks of Steven

Wright, Denis Leary, Lenny Clarke and Jay Leno, and gracing

the stages of the IMPROV, COMEDY STORE, FLAPPERS,

LAUGH FACTORY, and other noteworthy venues. He has

parlayed his success as a stand-up to firmly establish himself in

the film and television arena, featuring in several episodes of the

hit series “The King of Queens,” and recent guest appearances

on “Veep” on HBO and the Disney Channel’s “Bizaardvark.”

Jackie is currently seen in the series regular role of “Tony” in

“Loudermilk” (3 seasons on Netflix), which is Peter Farrelly’s

directing foray into television.“

He is also one of the proud winners of the prestigious San

Francisco Comedy Competition, as well as a featured performer

at the Montreal Just For Laughs Festival gala. He was chosen to

perform at the U.S. Comedy Arts Festival in Aspen, Colorado

produced by HBO.

Early on in his career, Jackie was discovered on stage in Boston

by the Farrelly brothers, who have since cast him in back to

back roles in “King Pin”, “There’s Something About Mary”,

“Me, Myself And Irene” “Shallow Hal” and “Stuck On You.”

Jackie has had prominent roles in “The Three Stooges”, playing

opposite Kevin James in “Here Comes The Boom,” as well as

the movie “Mall Cop”

Jackie recently shot “The Worlds Greatest Beer Run” in

Thailand , starring along side Russell Crowe, Bill Murray and

Zac Ephron, and recently “Ricky Stanicky” with John Cena and

William H. Macy.

Jackie’s golf background, popularity from a national Phil

Mickelson commercial, and relationships on the PGA and

celebrity golf circuit, make him an often requested headlining

comedian for affiliated and corporate event entertainment

including Bay Hill in Orlando FL, Bel-Air Country Club in Los

Angeles CA, The Hideaway Golf Club in Palm Springs, CA,

Trump Doral in Miami FL. Morgan Stanley, Hertz, IBM, Intel

and Yahoo to name a few.

Jackie is truly a “comic’s comic” whose refreshingly unique

brand of sarcastic observational humor puts him in a class all his

own, apart from the many derivative cookie cutter comics plying

the airways today. Audiences young and old appreciate his wit

and rapid-fire “take no prisoners” delivery.

ERIC TAYLOR

In addition to years of public service as Boston City Councilor and his current role as Vice President of City and Community affairs for Northeastern University, the name John Tobin is synonymous with Boston comedy. With over 30 years of experience in live comedy, John has cultivated a deep understanding of what it takes to consistently produce a memorable comedic production. Armed with a true gift of gab, John has a natural ability to develop and maintain relationships which has proven beneficial in both politics and entertainment.

A consistently packed calendar of top national headliners has opened the door for John to expand with clubs in new markets for a growing audience. John Tobin Presents will continue to seek areas for growth while maintaining the quality of excellence that New Englanders have come to expect from a John Tobin production.

TIM CROWLEY

Tim Crowley is a seasoned marketing professional with over 13 years working in the live entertainment industry. Prior to his role with John Tobin Presents, Crowley ran marketing for Worcester’s DCU Center, establishing a marketing approach that led to an increase in ticket sales revenue across all arena events including the 2018 NCAA Division 1 Men’s Ice Hockey Northeast Regional.

While at Live Nation’s NYCB Theatre at Westbury, Tim developed an integrated marketing strategy for over 100 events annually that contributed to a 44% increase in overall ticket revenue while decreasing our average advertising spent per paid ticket by 40%. In addition to these roles, Tim has held manager-level marketing positions with Barclays Center, Sesame Street Live, and the Lowell Auditorium promoting a variety of events such as Broadway shows, comedy, concerts, professional boxing, and college basketball, all of which contributed to a diverse mix of marketing awareness.

As VP of Marketing, Tim enjoys the privilege of developing marketing strategy for John Tobin Presents, Improv Asylum, and all related entities including but not limited to the following venues:
-Laugh Boston
-Laugh Louisville
-Improv Asylum
-Asylum NYC
-Nick’s Comedy Stop
-Off Cabot Comedy Club
-Detroit House of Comedy
-Roar Comedy Club at MGM Springfield
-The Comedy Scene at Patriot Place

RYAN COTT

Ryan Cott is the Managing Partner and oversees programming for all John Tobin Presents venues including Laugh Boston, Laugh Louisville, Nick’s Comedy Stop, ROAR Comedy Club, The Comedy Scene, Off Cabot Comedy & Events, The Detroit House of Comedy and all third party venues.

As Manager and Talent Buyer for the Comedy Connection in Boston’s Faneuil Hall Ryan developed a truly well rounded understanding of producing stand up comedy. Over the years Ryan has developed a keen eye for spotting promising comedic talent and a thorough understanding of how to shift with industry trends to please a diverse audience.

JOHN TOBIN

In addition to years of public service as Boston City Councilor and his current role as Vice President of City and Community affairs for Northeastern University, the name John Tobin is synonymous with Boston comedy. With over 30 years of experience in live comedy, John has cultivated a deep understanding of what it takes to consistently produce a memorable comedic production. Armed with a true gift of gab, John has a natural ability to develop and maintain relationships which has proven beneficial in both politics and entertainment.

A consistently packed calendar of top national headliners has opened the door for John to expand with clubs in new markets for a growing audience. John Tobin Presents will continue to seek areas for growth while maintaining the quality of excellence that New Englanders have come to expect from a John Tobin production.

Patrick Arnold

Patrick manages Social Media, Video Production, Box Office Operations, Booking Administration, and customer service for John Tobin Presents. In his time with JTP, Patrick has shot videos and pictures for Bill Burr, Jessica Kirson, Nate Jackson, Joe List, Lil Sasquatch, and many more local comedians. He currently produces Mike Binder’s Stand-Up World Podcast, he produced and edited Will Noonan’s “50 TikTok’s At Once” comedy special, and his edited works have received over 5 million views online. He has helped grow the John Tobin Presents social media accounts by over 15k followers in under 2 years.

Patrick started his professional career in the news industry as a storyteller and quickly shifted his media and production skills to the entertainment industry in Boston. He graduated Cum Laude from Northeastern University in 2023 with a degree in Communication Studies and a minor in Music Industry.