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.

Due to overwhelming response, Bluebird Improv has added a second LATE NIGHT show on July 22nd.

Note: The 7pm show runs until 8:30, so there will be a quick turnaround between shows. Expect a bit of lively energy as one crowd leaves and the next arrives – part of the fun of an improv double feature!

Get ready for a night of spontaneous comedy with Bluebird Improv. Over the past several years, Bluebird Improv has built a reputation you can trust – if you go to one of their shows, you know you’ll see high-caliber comedians and experience something hilarious, unpredictable, and completely original. Past performances have included Rachel Dratch (SNL) and Matt Walsh (Veep), and this year’s lineup promises to be just as exciting.

Each show begins with a quick chat with the audience, sparking entirely improvised scenes that you’ll only see that night.

Scheduled performers include:

(Cast is subject to change)

Marc Evan Jackson is best known for his roles as Kevin on Brooklyn: Nine-Nine; Shawn on The Good Place, attorney Trevor Nelsson on Parks & Recreation, and Mary Anne’s dad Richard Spier on The Baby Sitters Club. Marc is an alum of The Second City Detroit and his also one of the partners in the schooner Grace Bailey in Rockland, Maine.

Matt Walsh is a two-time Emmy-nominated actor from HBO’s award-winning comedy series Veep, and cast member of Apple TV’s acclaimed limited series Manhunt. He is also a founding member of the Upright Citizens Brigade Theater. Walsh will next be seen in Paramount Pictures Novocaine starring Jack Quaid, Maybe We Should starring Heather Graham, Little Lorraine starring Stephen Amell, and Utopia’s Not An Artist where he co-stars opposite Rza from the Wu Tang Clan. Recently, he appeared in Hulu’s Unplugging, which he co-wrote, and starred alongside Eva Longoria. He can also be seen in The Good Half starring Nick Jonas. Walsh has appeared in memorable roles in several popular comedy films including Life of the Party, Old School, Starsky and Hutch, Ted, and Keeping Up With The Joneses. Other credits include the CBS series Ghosts, Fox Searchlight’s Flamin’ Hot, and the recent Father of the Bride film. Walsh currently does a podcast Second in Command with his Veep co-star Timothy Simons. In addition to his film and TV work, Walsh is also a charitable founder of Open Book with his wife Morgan. The charity donates LGBTQ affirming books to public elementary schools around the country. Matt currently resides in Los Angeles with his wife Morgan Walsh and their three children.

 

Stephnie Weir is an actress, writer, comedian best known for her work on MadTv. She has a long list of acting credits – Crazy Ex-Girlfriend, Happy Together, The Comedians, Castle, Key&Peele, Veep, The Goldbergs, Modern Family, A Million Little Things, Night Court, Mighty Ducks – to name a few. She’s written on numerous television shows including Raising Hope and The Millers. She is a mainstage alumni of The Second City and I.O. Theaters in Chicago. She and her husband, Bob Dassie, have a long-running two-person improv show called “WeirDass.”

Tim Meadows is an actor, writer comedian who was one of the longest-running cast members on Saturday Night Live, where he appeared for ten seasons. Tim played John Glascot on the ABC sitcom The Goldbergs throughout its ten seasons and starred as the same character in Schooled for its two-season run. Meadows also played the school principal in the hit comedy Mean Girls and co-starred with Adam Sandler and Chris Rock in the blockbuster comedies Grown Ups and Grown Ups 2. Additionally, Tim co-starred with Andy Samberg in Popstar: Never Stop Never Stopping for Universal Pictures and co-starred with John C Reilly in Walk Hard: The Dewey Cox Story for Sony Pictures. He was seen multiple times in Brooklyn Nine-Nine, The Office, Miracle Workers, and the lead in CBS/Paramount’s No Activity. Tim has also voiced one of the main characters on Bob’s Burgers for Fox and starred in hybrid live-action/animated comedy, Son of Zorn, from Chris Miller and Phil Lord alongside fellow SNL alum Jason Sudeikis. Most recently, Tim starred in the Peacock series Poker Face, Disney+’s The Mandalorian, and Comedy Central’s animated series Digman!

Brad Morris is a veteran tv and film writer, producer, actor, director and improviser. An alum of four of Chicago’s Second City’s Mainstage revues, the iO Theatre and The Annoyance, Brad is a member of the renowned long form improvisational groups, The Reckoning and Uncle’s Brother with Tim Meadows. Brad has improvised around the world with the Second City National Touring company and Matt Walsh and Friends for the USO. As a TV writer, Brad spent three seasons as a producer on the TBS comedy, Cougar Town, was a producer on the Showtime series, Dice, and was co-ep and head writer for seasons 1 and 2 of the critically acclaimed series for Paramount and Seeso, Bajillion Dollar Properties. Brad has sold original scripts and development to ABC, TBS, Sony and Warner Brothers. On the film side, Brad co-wrote and produced the independent film, Unplugging, starring Matt Walsh and Eva Longoria. He is also producing the independent film, Stoners and Saints, starring Dylan Gelula and Matt Berry. Brad also recently co-wrote Family Squares, and a movie  for Paramount, Rear Naked Choke, produced by Margot Robbie. As an actor, Brad has starred as a series regular in several network and cable pilots, and has appeared on Curb Your Enthusiasm, Veep, Modern Family, The Office, The League, Key and Peele, Great News, Playing House, Dice, F is For Family, Friends From College and The Good Place. He has appeared in films, Search Party, Sing, A Futile and Stupid Gesture, and Jay Roach’s, Bombshell. Brad can also be heard on his new improvisational podcast, Business Trips that he co-hosts with Mike O’Brien.

Joe Canale has been improvising around the world for the past 30 years, including stints at Boom Chicago in Amsterdam and The Second City Mainstage in Chicago amongst many others. While he’s not made appearances in film and television his greatest pleasure is derived from performing live improv for an audience. He hopes you enjoy watching this show as much as he enjoys performing it.

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.