Before comedian Jimmy Tingle could start his newest gig, he had to make a visit to the roundabout.

Mr. Tingle takes up the gavel for the Art Buchwald Possible Dreams auction this weekend, and he visited the Vineyard last week to meet with event organizers and the staff of Martha’s Vineyard Community Services. The auction is the principal annual benefit for Community Services and takes place Sunday, July 28 at the Winnetu in Edgartown. The day and date are changed this year from the traditional first Monday in August.

The auction features one-of-a-kind unbuyable items and experiences — including the old blinker light from the former four-way stop.

Hence Mr. Tingle’s trip to the roundabout.

“It was pretty funny,” he said. “I guess that’s Island life—a roundabout can take on a whole new meaning.”

No stranger to Vineyard shores, Mr. Tingle has been performing comedy shows here since the days of the Hot Tin Roof and the Wintertide Coffeehouse. In October he screened his latest film at the Martha’s Vineyard Film Center. “The audiences are always great. You have the Massachusetts population but also people from all over the country and all over the world,” he said. Possible Dreams chairman Sandy Pimentel contacted Mr. Tingle earlier this year about helming the event. Interest piqued, he sent off an audition tape — his latest one-man comedy special Jimmy Tingle for President: The Funniest Campaign in History, in which he campaigns on the Humor for Humanity ticket.

He got the job.

“I’m just thrilled, really excited,” he said in an interview last week. “I really want to make it as successful as possible.”

Born in Cambridge, Mr. Tingle began performing stand-up in Boston in the 1980s. He holds the record for the longest-running one-person show at the Hasty Pudding Theatre, he has worked as a contributor for CBS and MSNBC, and has made guest appearances on The Tonight Show and Late Night with Conan O’Brien. In 2001 he won a Best of Boston award for stand-up comedy. Mr. Tingle has also turned in the occasional acting role — look for him in Head of State and Boondock Saints. He gave the 2010 Commencement Address at Harvard University.

Though stand-up comedy is his main profession, while performing fundraising shows, he would occasionally be asked to help out with an auction at the same event. Informal requests to help out evolved into a more formal role as comedian-emcee-auctioneer, he said. The roles certainly have their similarities — working the crowd, improvising, holding an audience’s interest, and of course, entertaining.

“You learn on the job,” he said. “You write out your material, think about what you want to say . . . but it’s trial and error.”

Laughter has long been associated with the Possible Dreams auction. The late humorist Art Buchwald chaired the auction for decades, and this year the event was named in his honor.

“It’s great to be included with something that Art Buchwald was so involved with and so passionate about,” Mr. Tingle said. “This is something that we can do right here in our own backyard, for friends and neighbors.”

Last year’s auction raised more than $400,000.

Martha’s Vineyard Community Services, the Vineyard’s oldest social services umbrella organization, serves more than 6,000 people annually, through its early childhood programs, disability services, mental health counseling, domestic violence prevention and the Chicken Alley thrift store.

“It’s incredible to see how many volunteers are working on this so diligently, and how committed everybody is,” Mr. Tingle said. “It’s pretty inspiring.”