New York vs. Boston Comedy Series

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 Boston: Kevin Flynn

Former pro soccer player turned comedian, Kevin Flynn has excelled in comedy, acting, and hosting. Founder of the Nantucket Comedy Festival, he blends entertainment with a passion for youth education.

Team New York: Don Jamieson

Emmy Award-winning comedian Don Jamieson is best known for co-hosting VH1 Classic’s That Metal Show. With sharp humor and a love for rock music, Don delivers acerbic takes on pop culture and life’s absurdities.