The Wicked Good Musical Revue celebrated its 10th anniversary last weekend with a series of sold-out performances at the Martha’s Vineyard Playhouse that took audiences on a whirlwind tour of musical theatre highlights from the past 90 years.

The engagement’s generous program — 28 songs in all — was also a retrospective of the Wicked Good troupe’s own history of off-season revues, with singers reprising their favorite numbers from past years.

The anniversary troupe was extra-large as well, with original members Shelagh Hackett and Paul Munafo rejoining Wicked Good co-founders Molly Conole and Ken Romero and more-recent members Jenny Friedman, David Behnke, Katherine Reid and Rachel Cooke.

Katherine Reid and Jenny Friedman. — Mark Alan Lovewell

Gleaming in evening wear, the eight singer-actors entered two by two as they sang Old Friends, from Stephen Sondheim’s 1981 show Merrily We Roll Along.

The entire cast later gathered in harmony for Sondheim’s Side By Side (Company, 1970) and the title song from 1997’s Ragtime, by Stephen Flaherty and Lynn Irons. They both sang and danced to Fats Waller’s The Joint is Jumping (a 1937 number rearranged for the 1978 musical Ain’t Misbehavin’) and provided a kick line for the hilarious A Musical, from the 2015 show Something Rotten by Karey Kirkpatrick and Wayne Kirkpatrick.

Longtime collaborators Mr. Munafo and Ms. Hackett paired up for two very different duets, displaying the versatility of both performers.

In the quizzical Do You Love Me, from Jerry Bock and Sheldon Harnick’s 1964 hit Fiddler on the Roof, a husband and wife explore their feelings 25 years after they met on their wedding day. Sondheim’s A Little Priest, from Sweeney Todd: The Demon Barber of Fleet Street (1979), sees the bloodthirsty Todd and Mrs. Lovett the baker cook up a monstrous menu of man-pies.

Ken Romero and David Behnke. — Mark Alan Lovewell

Mr. Munafo further displayed his comic-acting chops as a chef in Les Poissons, from John Musker and Rob Clements’s The Little Mermaid (2007), and — alongside Ms. Conole and Ms. Hackett — as a scheming villain in the trio Easy Street, from Charles Strouse and Martin Charnin’s 1977 Annie.

Ms. Hackett also transformed into Ado Annie, from Richard Rodgers and Oscar Hammerstein’s Oklahoma! (1943), with the durable comic lament I’m Just a Girl Who Can’t Say No.

Ms. Friedman stepped into the spotlight for To Keep My Love Alive, written by Richard Rodgers and Lorenz Hart for their 1943 revival of A Connecticut Yankee in King Arthur’s Court.

As Queen Morgan le Fay, reminiscing in brisk rhymes about the various husbands she’s bumped off in order to avoid adultery, Ms. Friedman’s deadpan performance had audience members chuckling out loud.

Choreographer Ken Romero puts on his tap shoes. — Mark Alan Lovewell

Mr. Romero, a Vineyard native who returned to the Island after his international show-business career was derailed by the pandemic, broke out his tap-dancing shoes for a crowd-pleasing solo in A Musical. His duets with Mr. Behnke included the heartbroken Lily’s Eyes, from Lucy Simon and Marsha Norman’s The Secret Garden (1991) and a gender-flipped, laugh-out-loud rendition of Bosom Buddies, originated by Angela Lansbury and Bea Arthur in Jerry Herman’s 1966 show Mame, for which both women won Tony awards.

Other highlights from the anniversary show include It Couldn’t Please Me More (A Pineapple) from John Kander and Fred Ebb’s 1966 show Cabaret, with Ms. Conole in the role originated by Lotte Lenye and Mr. Behnke as a boarder courting her with fruit.

The troupe’s youngest members, Ms. Cook and Ms. Reid, both shined in emotional solos from 21st-century musicals. Ms. Cook’s stirring performance of She Used to Be Mine, a pivotal aria from Sara Bareilles’s 2015 show Waitress, left Friday night’s audience so stunned that it took a long moment before applause and cheers erupted from the seats.

Singing No One Else, from David Molloy’s 2016 musical Natasha, Pierre and the Great Comet of 1812, Ms. Reid radiated the joyful spirit of a young woman recalling the first time she met the man she loves.

Mr. Behnke was musical director for the anniversary revue, taking over from Ms. Conole, who first came up with the Wicked Good Musical Revue idea 10 years ago.

Mr. Romero choreographed the show, while pianists Molly Sturges and Peter Boak — also longtime members of the troupe — took turns accompanying the singers and turning the pages of each other’s sheet music.

Friday’s show ended as Wicked Good Musical Revues always do: with a standing ovation, lots of cheers and a chance to meet troupe members in the lobby.