Boston’s best comedians continue to come to Dreamland Ballroom

Jackie Flynn. — Photo courtesy of Dustin Dumas

Comedian Jackie Flynn headlines A Night of Comedy at the Dreamland Ballroom in Oak Bluffs on Sunday, July 29. Nick’s Comedy Stop, Boston’s longest-running comedy club, will send three of Boston’s finest comedians down to the Island for a night of quality comedy.

Along with being a fixture in Boston comedy clubs, Mr. Flynn has had many roles on the silver screen. Found in Boston comedy clubs by the Farrelly brothers, he has played parts in a number of their movies, including “There’s Something About Mary,” “Me, Myself & Irene,” and “Stuck On You.” In television, he has had repeated cameos on “The King of Queens.”

In a commercial where he plays a befuddled golfer who gets a lesson in integrity from Phil Mickelson, Mr. Flynn says as much with his facial expression and active eyebrows as anything. He is also one of the “men of the square table” in Miller’s “Man Law” commercials, in which he got Burt Reynolds to change his position on how long one must wait to date a friend’s ex-girlfriend by appealing, “What if she’s drop-dead gorgeous?”

Mr. Flynn’s stand-up is filled with salty observational humor, with self-deprecating anecdotes interspersed throughout an act. In one veteran bit he told a two-part joke where the first part of the joke is intentionally deadpanned, and it was his ensuing remarks that drew heavy laughter. He led with, “My back’s really messed up, I had to go to a chiropractor, that’s how bad it was. He couldn’t fix it, had to send me to a paleontologist.” There was a laughless pause, which Mr. Flynn broke by saying, “Which is the guy who works with dinosaur bones, if you didn’t get that. If you know the words the jokes are funnier.”

Young Boston comedians Will Noonan and Graig Murphy will join Mr. Flynn onstage. Along with his comedy, Mr. Murphy appears on WEEI sports radio. Mr. Noonan has a live show CD out, and has performed at clubs, colleges, and casinos across New York and New England.

The show is $20. Tickets ($20) are available at