Actor Tommy Simon has an unmistakable Woody Allen–esque quality. Distinctive voice, nervous streak a mile wide, little skinny guy with glasses...he can naturally turn on what the legendary playwright and filmmaker has made into a calling card. And here, with Magenta Giraffe Theatre and director Frannie Shepherd-Bates, Simon takes a stab at the classic Allen protagonist in the legend's own Play it Again, Sam. Casting a Woody Allen type for an Allen play seems like a slam dunk, but it carries considerable risk: the actor's innate similarities to the iconic original cannot help but invite comparison, which may leave the viewer wondering whether this is merely mimicry. Having seen Simon's work before, I was able to discern and appreciate the actor's own fresh (if often reminiscent) take on the character of Allan Felix. Many of the choices worked in their own right, adding a flurry of activity and energy to Allen's usual subdued pacing and hand-wringing, yet I couldn't help thinking that a few moments might have gone better were they done Allen's way.

Certain themes and scenarios loom large in the playwright's body of work, and this one is no exception, despite dating back to 1969: here's a real loser of a man, with equally high and low opinions of himself, obsessed with sex, in a New York setting. Recently divorced but longtime head case Allan is adrift in the first act, enlisting the help of best friend Dick (Stephen Blackwell) and Dick's wife, Linda (Jaclyn Strez), to provide emotional support and, even better, an attractive woman to fill the void in his life. The man is an utter mess, in no shape to meet anyone, which is proven in an overblown slapstick scene in which Simon's trying too hard tries too hard. Dick's officious inattention to anything but work makes him live up to his name, and sets the stage for Allan to loosen up and be himself in Linda's company. The story blossoms along with the affection between Allan and Linda, which goes exactly as one would expect, given the source. Surprises are few, but the real draw of this production is the skewed self-damning perspective and sharply awkward dialogue for which the writer is known.

Throughout the play, Allan's recall and tendency to hypothesize take physical form, with support from Kira Frabotta and Kennikki Jones in multiple roles. Interestingly, as the real-time actions of the play find a calmer ground, the imagined scenarios grow increasingly cinematic and stylized, to the great benefit of both. On the small stage of 1515 Broadway, Gwen Lindsay's detail-laden set and Shepherd-Bates's staging don't always give these asides the space they deserve, but once the fantasy sequences graduate to their own lighting effects (Neil Koivu) and soundtracks (Shepherd-Bates), they're simply hilarious. A professional film buff, Allan is also visited by the specter of the ultimate celluloid man, Bogey; Brian Papandrea's portrayal of another classic film face is a collection of affectations, and the device can feel like an extraneous added layer, but the character's effusive cigarette waving and misogynistic threats are so far outdated as to invite plenty of wry laughter.

In the non-imagined world of the play, Simon's journey from a swaggering embarrassment taking his cues from old movies to a harmless sweetie comfortable without the safety of artifice doesn't quite stand on its own as a through line. Rather, his best work is opposite the sensitive and lovely Strez, whose Linda is fully realized and rewarding to watch, even when she's in the background. Together, the two have charming chemistry and push just the right buttons for the audience to root for each decision they make. Blackwell is just awful enough without becoming odious, as brash and tone deaf as his outrageous costumes (by Katie Casebolt).

This production of Play it Again, Sam feels much longer than its ninety-odd minutes, but this is certainly the result of the baffling three-act structure, with two intermissions when none would have sufficed. The show bravely and convincingly tackles one of the most distinctive auteurs of the late twentieth century, with the end product a familiar interpretation, but certainly not a mere imitation. A fun throwback to his silly early flavor of comedy, the production should have particular draw for Allen fans, but the cutting humor and lovable treatment of its main characters also holds a broader romantic-comedy appeal.