Criticism comes from some unexpected places when you’re a playwright attempting to star in your own play. That much is true for New York playwright Sam Forman, whose play The Rise and Fall of Annie Hall opened in preview last night at the Vineyard Playhouse (official opening night is Saturday). He’s seen the central role of Henry played by others in the three years since the play was written, and he has heard the actors lodge lighthearted complaints about the challenges posed by the dialogue. But before now, he’s never experienced it firsthand.

“I’m finding that they’re right,” said Mr. Forman this week, of the play’s former Henrys. “I might even be annoyed with this writer, if I weren’t him,” he confessed with a smile.

All joking aside, New York based director Johanna McKeon described the play as a smart and proper comedy, and one that’s sure to delight Vineyard audiences eager to bring belly-laughter back to the playhouse.

The play focuses on a young New York playwright on the brink of his 30th birthday. Dissatisfied with the level of success he’s seen so far in his career, Henry embarks on a lofty quest to transform the Woody Allen cinema classic, Annie Hall, into a stage musical fit for Broadway. And he doesn’t hesitate to step on former allies along the way. While it’s not autobiographical, Mr. Forman said that the play definitely draws from his own experiences in the theatre world.

“I live in New York city,” said Mr. Forman. “The play is sort of inspired by that world of very ambitious young theatre people, who are all trying to make it on Broadway, and the kinds of things that people do in that effort to succeed.”

It’s been years since the playhouse has staged a full-out comedy, Ms. McKeon said. She lobbied hard for The Rise and Fall of Annie Hall when she was brainstorming plans for a summer production with playhouse artistic director M.J. Bruder Munafo. The play, she said, was fresher than the rest. “This was by far the funniest of the plays that I suggested,” she said in the joint interview with Mr. Forman, as they took a break Wednesday morning from this week’s laborious rehearsal schedule. “This is a new play, and typically when people do comedies they’re sort of reviving the old standards.”

The actor and director pair seem well-suited for a comedy, and laughter is clearly an abounding element in the relationship, which long precedes their collaboration on the Vineyard. They’ve crossed paths on the New York theatre circuit for years, and last summer worked together on a musical production written by Mr. Forman at the Williamstown Theater Festival.

So a certain level of trust already had been established when Ms. McKeon approached Mr. Forman several months ago about starring in his play. Just like Woody Allen had, in so many of his films, Ms. McKeon felt that the writer behind this work also belonged in the starring role.

“That was my idea. I sort of floated it in a very theatre-y bar in midtown [Manhattan] a few months ago. Sam met me after work for a drink, and it was like midnight, and we’re sitting in this bar, Angus, that’s actually referred to in the play. And I just said ‘Sam, if we’re going to do it, I really think you should play the lead. It only makes sense.’”

It wasn’t a tough sell for Mr. Forman, especially considering the location. With family living on Nantucket, he’s been a frequent visitor to the Vineyard in years past, and he thought it would be a nice change of pace from the bustle of the big city. So far, it has been.

“We go to the beach every day after rehearsal, as opposed to going to like 17 scheduled meetings after rehearsal, which is what happens when you’re in New York,” said Ms. McKeon. The cast is comprised of a handful of friends from the city, so the production has had a home-like feel in a decidedly laid-back setting.

“We’re still fighting hard to put on a two-act comedy,” said Mr. Forman “It’s a tight rehearsal process and it’s intense in there, but when you come out the door, you’re in a beautiful place, instead of coming out into midtown Manhattan.”

The play itself focuses on the struggle of an aspiring playwright, but does Mr. Forman feel as if he’s already surpassed that stage in his career? “You’re always trying. Playwrighting itself is not a very secure profession. You can always do better. I don’t think there are any playwrights that feel like they have totally arrived. You’re only as successful as your last one and you kind of have to keep making things that people want to see.”

Ironically, he’s given his lead character in The Rise and Fall of Annie Hall a project that probably wouldn’t be very well-received in the theatre world. “Part of the big joke of the whole thing is this guy’s on this mission that might not even be a very good idea,” said Mr. Forman. “While it’s my favorite movie in the world, and I think it’s a lot of people’s favorite movie that I know, it probably wouldn’t make a very good musical.”

The play itself is not a musical, but there are two musical numbers included. For the sake of comedy, and no doubt to satisfy the audience’s curiosity as to how one might go about setting Annie Hall to music, one of the songs is from the imagined Broadway hopeful. “For people that like Annie Hall, it’s a pretty cute song,” said Mr. Forman. “It kind of hits on all the big scenes in Annie Hall...It makes a lot of funny allusions to the movie.”

Ms. McKeon described the film as a “serious backstage insider comedy,” but Mr. Forman said you don’t have to actually be an insider to identify with Henry’s plight. “You don’t have to be obsessed with theatre to enjoy it. You can understand that everyone’s obsessed with something, particularly in somewhere like New York city, that’s a hub of all these obsessive, ambitious people,” he said.

The play opened with a preview last night, but the opening night reception will be held after the 8 p.m. performance tomorrow at the playhouse. It won’t be Mr. Forman’s first attempt at acting. In fact, he had acted and written plays through most of his life. But starring in The Rise and Fall of Annie Hall has exposed the writer to new elements of his own piece.

“I’m sort of the eyes of the audience. I talk directly to the audience and nobody else does. I’m in basically every second of the play, so it’s huge. It’s a big part, actually, for anyone,” he said.

“The two guys that had done it before were definitely telling me along the way that it was a challenging role. Now I see that they were correct.”