Island Entertainment has rented its last movie, but remains a cultural touchstone for generations of Islanders who browsed and worked at the beloved video store over its more than 30 years in business.

Saturday night at the Katharine Cornell Theatre, three generations of the Vineyard’s music and theatre community saluted the store with That’s Island Entertainment, an evening of songs from movies both illustrious and obscure.

Produced and emceed by actress and singer Shelagh Hackett, one of many people in the house who had worked at the video store, the concert featured more than a dozen singers and musicians—from middle schoolers to show business veterans—performing nearly 30 numbers made famous in films.

Among those joining her were Boaz Kirschenbaum on keyboards and vocals; multi-instrumentalist Brian Weiland and his son Aiden on violin; singer, actress and former Island Entertainment employee Chelsea McCarthy and her mother Taffy McCarthy, an actress, singer and director who also plays guitar.

The songs ranged from sentimental ballads like Dream a Little Dream of Me, featured in films including French Kiss and sung by Oak Bluffs School student Ava McGee, to rocking rave-ups like a medley of songs from 1975’s Rocky Horror Picture Show performed by guitarist and singer John O’Toole, Mr. Kirschenbaum and drummer Rob Soltz as audience members danced in the aisles.

The set list had plenty of Oscar winners, including The Morning After from The Poseidon Adventure, Moon River from Breakfast at Tiffany’s and this year’s Shallow from A Star Is Born.

There were also overlooked gems like Pure Imagination from Willy Wonka and the Chocolate Factory, and two songs made famous by Harry Nilsson—Everybody’s Talkin’ from Midnight Cowboy and Me and My Arrow from The Point!

Anne Evasick, who owned Island Entertainment for all but four years of its existence, and her longtime manager Jamie Alley were the guests of honor. Decked ceremonially with shoulder sashes and paper crowns, they presided as from a royal box in the balcony for the first half of the show, and descended to audience level after intermission.

Ms. Evasick, wearing a sash that read The Smartest Person in the World, beamed throughout the performance and chatted with fans during the break. Mr. Alley, whose sash read Cinematic Savant, took the stage himself, opening the second half of the concert with The Shadow of Your Smile, the Oscar-winning song from The Sandpiper. Guitarist Eric Johnson accompanied Mr. Alley, who introduced the song as his mother’s favorite.

Among the evening’s many highlights were several performances by former Vineyard resident Elizabeth Wojtusik, who delivered a showstopping, defiant Cry Me A River from The Girl Can’t Help It, accompanied by Mr. Johnson. She also duetted with Ms. Hackett on Over the Rainbow, the two singers improvising and harmonizing with Mr. Weiland.

Taffy McCarthy also sizzled on guitar and voice, especially with Mr. Weiland on bass in Ode to Billy Joe. Ms. McCarthy and Mr. Weiland are longtime teaching comrades at the Oak Bluffs School, where they have produced student musicals for many years. Their next production of The Point! opens May 30. Saturday’s audience got a preview from Aiden Weiland, Ms. McGee and Emma Burt singing Me and My Shadow.

A former Oak Bluffs School musical star, Duncan Pickard also joined the program, reprising his seventh-grade performance as Harold Hill in The Music Man with Ya Got Trouble. In the front row, Taffy and Chelsea McCarthy and Ms. Hackett jumped up and chorused as the Mothers of River City.

“When you’re a kid growing up on Martha’s Vineyard in the 1990s, there’s no cooler place to hang out than Island Entertainment,” Mr. Pickard, now an attorney in New York city, told the audience.

Donning a series of increasingly glamorous gowns, Chelsea McCarthy assisted Ms. Hackett as concert emcee and also joined her friend on the theme from Valley of the Dolls, with Mr. Johnson accompanying.

“This was an absolute store favorite. We watched this movie all the time,” Ms. Hackett said.

Along with more than two dozen vocal selections, the concert included a pair of instrumental fiddle tunes performed by Aiden and Brian Weiland: Concerning Hobbits from The Lord of the Rings and Hedwig’s Theme from the Harry Potter series.

Another generational duet featured pianist Charlie Esposito backing up his son Adagio, who delved into the dark and questioning character of Pumpkin King Jack Skellington in Jack’s Lament from A Nightmare Before Christmas.

But the evening truly belonged to Ms. Hackett, who not only produced the concert but sang gorgeously throughout, though from time to time she had to pause for a few tears.

“This is for Jamie and Anne and for the video store,” she said, before singing Dolly Parton’s I Will Always Love You from The Best Little Whorehouse in Texas with Brian Weiland on guitar.

Mr. O’Toole and Mr. Kirschenbaum then returned to the stage with a highly dramatic, two-man rendition of Queen’s Bohemian Rhapsody. Like Ode to Billie Joe, this wasn’t originally a movie song, but as a beloved element of the 1992 comedy Wayne’s World, it ended the evening on a high note.