The Possible Dreams auction and fundraiser raised $795,000 for Martha’s Vineyard Community Services, the near-record amount adding over $100,000 from last year’s total.

The live auction held Sunday at the Winnetu Oceanside Resort and an ongoing silent online auction make up the organization’s largest fundraiser of the year.

“In spite of the heat, people were so generous,” said Barbara Bellissimo, a consultant and Possible Dreams committee member. Last year, the auction raised $670,950, and in 2021 it raised $480,000.

Beth Folcarelli, CEO of Community Services. — Jeanna Shepard

The 45th Possible Dreams event was hosted once again by Seth Meyers and professional auctioneer Sherry Truhlar, who teamed up to auction off eight ‘dreams.

The first item, A Dream Fit for a Foodie, kicked off the bidding, setting the auction’s tone with two results. One winner who bid $26,000 received the full package, which included a cooking class for up to 10 guests from Vineyard Golf Club’s chef Anthony Rabeni, dinner for six and one growler each at Offshore Ale Co, an afternoon of margarita lessons from Dos Mas/Taco MV, a half-day cooking lesson with Bombay Indian Cuisine and a variety of gift cards to local restaurants.

Then Chef Rabeni threw in an additional item: one winner who bid $20,000 also received the private cooking class.

A day on the set of hit television show Yellowstone went for $20,000 and attending a taping of Finding Your Roots with Henry Louis (Skip) Gates JR. sold for $9,000.

Seth Meyers (right) with chef Anthony Rabeni. — Jeanna Shepard

In the highest single bid of the afternoon, dinner and a movie with actor Jake Gyllenhaal and director Doug Liman went for $55,000. Up to eight guests will see the rough cut of Mr. Gyllenhaal’s latest film, Roadhouse, while eating pizzas cooked by Mr. Liman using the sourdough crust Mr. Gyllenhaal perfected during Covid.

Ms. Truhlar and Mr. Meyers joked with the audience throught the event, encouraging bidders to increase their generosity.

“Folks, I will tell you this, they print money everyday in DC,” Ms. Truhlar said. “It’s only money — these are experiences. If you want to drain the 401K, now’s the time to do it. You don’t want the kids to have it. It’s bad for them.”

One experience featured dinner at Mr. Meyer’s home in Chilmark with his in-laws, and actors Tony Shalhoub and Brooke Adams. As the bidding increased, Mr. Meyers sweetened the deal, adding comedian Amy Schumer and actor Kristen Wiig to the guest list and promising karaoke and a game of celebrity, which he said is particularly fun to play with celebrities.

Professional auctioneer Sherry Truhlar. — Jeanna Shepard

The winning bidder paid $51,000 for their seat at the table, which Mr. Meyers said was a small price to pay.

“If I didn’t know my in-laws, I would want to have dinner with my in-laws,” Mr. Meyers said in an interview with the Gazette after the auction. “I think that whoever has dinner with that group of people will walk away thinking that Tom and Joanne [Ashe] were the most interesting people, even though everyone else there was so much more famous.”

Taking a cue from Mr. Meyers, donors made more amendments to their items, adding a second private party for 40 at The Ritz in Oak Bluffs for $25,000, and two additional winners to see Late Night with Seth Meyers. The three winners each paid $37,000 to attend Mr. Meyers’ show once the writers and SAG-AFTRA strikes end, contributing a collective $111,000.

“When we are back in business, we are going to be so happy to do our show again. We miss it so very much,” Mr. Meyers said.

Wiet Bacheller with Tamara Buchwald. — Jeanna Shepard

The audience on Sunday was also filled with grateful recipients of Community Services services. Matt Moore, general manager of the Winnetu, said through tears that the organization’s counseling services saved his daughter’s life.

After the auction, Community Services presented its inaugural Art Buchwald Award for Outstanding Community Service to former MVCS board member and educator Wiet Bacheller. Recognizing Ms. Bacheller, the organization also acknowledged the community-wide effort imperative to the organization’s success.

“The board of directors is grateful for the outpouring of generosity we saw today from the island community,” Community Services board president Michael Goldsmith wrote in an email to the Gazette the next day. “We can’t say enough in praise of the artisans, business owners and other folks who chose to donate their time and energy to make the dreams a reality.”