Reserved Seating: $25 - $30 Advance | $35 - $40 Door
Doors 7pm | Show 8pm
New York vs. Boston Comedy Series comes to Vinegar Hill on September 6th!
The rivalry between New York and Boston has long been a battle of wit and grit, extending beyond sports, politics, and even bootlegging. Enter the New York vs. Boston Comedy Series—a hilarious showdown where comedians from both cities take the stage in a side-splitting face-off. Originating in Nantucket, the series later moved to Bridge Street Live before finding its home at Vinegar Hill. Since its debut in 2010, this annual event has delighted audiences with its unique blend of humor and hometown pride. Featuring top comedic talent from both cities, this playful clash of styles continues to captivate, proving that laughter truly is the best rivalry.
Host: Mark Riccadonna
Mark Riccadonna is a comedian, actor, and storyteller known for his engaging humor. With a theater background and global performances, including for US and UN troops, Mark brings relatable comedy to life. His latest Dry Bar Comedy Special, Domestic Nomad, highlights his signature storytelling style.
Team New York: Kevin Flynn
Kevin Flynn is an award winning actor, writer, producer, host, and comedian.
Starting out as a professional soccer player, Kevin made the transition to standup comedian by winning the prestigious Boston Comedy Riot. Since that time, Kevin has gone on to make numerous television and film appearances as a comedian and actor.
Kevin can be seen as The Wedding Coordinator in The Heartbreak Kid with Ben Stiller; in Me, Myself and Irene with Jim Carrey; in Osmosis Jones with Bill Murray; and as Charlotte’s Boyfriend in HBO’s Sex and the City. His character, Bram Walker, was voted one of the most popular boyfriends in the series. Kevin recently completed a role in the movie The Worlds Greatest Beer Run with Russell Crowe and Zac Efron.
While constantly acting and performing standup around the country, Kevin also works as a host and entertainer in the sports world. Flynn has covered World Cup Soccer for Fox Sports, ESPN, and ABC. Flynn’s show, SportsFigures on ESPN, received the POLK Award for excellence in children’s programming. He also created a weekly sports podcast for the ESPN Network called Over the Ball. The show combines the worlds of soccer, comedy, and entertainment. The show has been named MLS Talk Show of the Year.
In 1996, Kevin was the host of The Discovery Channel’s Go For It, an extreme outdoor adventure show where he swam with sharks, jumped out of airplanes, and scaled dangerous peaks. The show led Kevin to create his first one-man show, The Go For It Guy, which won the Best of Fest at the Boston Comedy Festival and HBO’s U.S. Comedy Arts Festival in Aspen.
Kevin is currently touring nationally with his latest one-man show, Fear of Heights—A Very Funny Phobia.
Along with continually performing his stand-up, Kevin is also the Founder and Executive Director of the Nantucket Comedy Festival. Each summer, the festival brings top comedic talent to Nantucket Island as the major fundraiser for Stand Up & Learn™, an island-based, year-round comedy education program serving Nantucket’s children. He is in the process of launching the Stand Up & Learn program nationally.
Team Boston: Jackie Flynn
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.” He is also recognized from his role along side the likes of Burt Reynolds, NFL Coach Jimmy Johnson and Jerome Bettis as one of the "Men Of The Square Table" in the hugely popular Miller Lite "Man Law" commercials. Jackie is currently seen in the series regular role of “Tony” in “Loudermilk” (DirectTV Audience Channel), 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.” Recently, Jackie has had prominent roles in “The Three Stooges,” playing opposite Kevin James in “Here Comes The Boom,” and 2017's film “Special Unit.”
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.
Vinegar Hill Music Theatre is an independently-owned event space located at 53 Old Post Road in Arundel, ME. Our charming, historic barn and outdoor garden provide an ideal backdrop for an unforgettable, intimate evening! Learn more here.
