SpeakEasy Stage Company tops off its 20th-anniversary season with a delightful production of a Tony-winning, comic valentine to the musical.

The Drowsy Chaperone. Music and lyrics by Lisa Lambert and Greg Morrison. Book by Bob Martin and Don McKellar. Directed by David Connolly. Presented by SpeakEasy Stage Company at Roberts Studio Theatre, Boston Center for the Arts. Extended through June 19.

By Evelyn Rosenthal

Will McGarrahan (Man in Chair) and Karen MacDonald (Drowsy Chaperone).Photo: Stratton McCrady.

The Drowsy Chaperone has it all: singing, dancing, and every trick in the musical comedy book. Which is, in fact, the point. The play, which won 2006 Tony Awards for score and book, started life as a bachelor party entertainment for the wedding of coauthor Bob Martin and fellow comic Janet Van De Graaff. The couple’s friends—like them, members of the remarkable Toronto comedy scene that includes Second City and spawned the acclaimed TV series about a struggling Canadian Shakespeare festival company, Slings & Arrows—whipped up a parody of the backstage Broadway musical (and its movie imitators) that turned into a real—and very funny—Broadway musical stocked with plenty of the usual suspects.

In the SpeakEasy Stage Company’s excellent production, the opening set is a dingy apartment with a worn easy chair beside a retro “entertainment center”—an orange crate full of records, a tuner and turntable, a couple of small speakers. Musical theater memorabilia covers the wall: sheet music showing Bing Crosby in mid-croon and Judy Garland selling “The Trolley Song”; photos of Funny-Girl-era Barbra Streisand and a bowler-topped Liza Minelli in Cabaret. The lights go down—and stay down. A voice in the darkness asks if we know that feeling of sitting in a darkened theater in delicious anticipation just before the lights come up and the dazzling world of a Broadway musical unfolds.

The voice belongs to the character known only as Man in Chair, who is eager to share his theater likes and dislikes (he doesn’t like the breaking of the fourth wall, he says, while doing just that). When the lights come up, he invites us to listen in while he plays his prized possession, a recording of his favorite musical, The Drowsy Chaperone. Spinning the LP is his cure for “feeling blue,” taking him—and the audience—back to the early days of musicals, when what are now clichéd plots and characters were young and fresh and entertaining. The set morphs into a brightly lit, colorfully painted mansion, and the musical begins.

McCaela Donovan (Janet Van De Graaff) and company members in The Drowsy Chaperone. Photo: Stratton McCrady.

A glamorous leading lady (named Janet Van De Graaff) is about to marry a rich man (Robert Martin, of course) and leave her acting days behind; her producer (Feldzeig—get it?) wants her to stay, and his chorine girlfriend (Kitty) wouldn’t mind replacing her; the producer deploys a Latin lothario (Aldolpho) to seduce the bride away from her groom; a spacy dowager (Mrs. Tottendale) hosts the wedding, aided by her put-upon butler (Underling); two gangsters masquerading as pastry chefs are sent by their investor boss to warn the producer not to lose the star; a female aviator (Trix) shows up just in time to save the wedding day when plans are botched by the best man (George); and the leading lady’s confidante/caretaker (The Drowsy Chaperone) tipples away and dispenses alcohol-addled advice. Mistaken identity and misunderstandings make their usual mischief.

If you feel like you’ve seen these characters and plot twists before, that’s because you have—in Marx Brothers and Fred Astaire vehicles and, especially, in Kiss Me Kate. Here, though, familiarity breeds hilarity, as the device of the spinning record, with its starts, stops, and even skips, takes the comedy up more than a few notches.

As Underling, Robert Saoud channels his inner Eric Blore—the seriously droll, perennial butler/valet in countless film comedies—and perhaps his inner Jacques Cousteau as well, in a series of spit-takes played perfectly with Kerry Dowling’s Margaret-Dumont-inspired Mrs. Tottendale. You can see the set-up coming from miles away: in a nod to Prohibition, Mrs. T. declares the code word for “vodka” will be “ice water,” and then asks for ice water, expecting the real thing. But that’s part of the fun—knowing what’s coming, and then being surprised by the play’s take on it.

Thomas Derrah (Aldolpho) in mid-seduction.Photo: Stratton McCrady.

Man in Chair is played by Will McGarrahan with just the right mix of glee (the joy he takes in the musical) and prickliness (anger whenever the world, in the form of a ringing telephone, intrudes). In a challenging directorial move that’s smoothly executed, the musical’s action stops whenever Man in Chair answers the phone, uses the bathroom, or most often, comments on the show within the show and the fictional actors playing its characters. He gives us the dish on the demise of the actor who played the egotistical Aldolpho—half-eaten by his own poodles—and on Beatrice Stockwell/Drowsy Chaperone’s penchant for “rousing anthems.” The preening, caped lover ends up seducing the wrong bride, and it’s a joy to watch Thomas Derrah wring all the comic juice out of the role, especially in his scenes with the impeccable Karen MacDonald, who also gives a hilarious double reading to “As We Stumble Along” as both the chaperone and the scene-stealing, anthem-loving Beatrice Stockwell. The chance to see these two expert Boston-area actors together is the icing on the (wedding) cake.

In other highlights, David Christensen as Robert and Brian Swasey as George turn in an admirable tap dance to “Cold Feets”; Sarah Drake manages to make the squeaky-voiced, airhead Kitty adorably appealing, and McCaela Donovan is a lively, saucy Janet, especially in her big number, “Show Off”—where she unconvincingly kisses off the theater life she’s about to ditch for marriage. That and the surreal “Bride’s Lament” are two of the funniest songs in the witty score, which captures both the cheese and the charm of the 1920s musical while playing to a 21st-century sense of satire. And mention must be made of the SpeakEasy show’s costumes—the finale offers designer Seth Bodie the chance to dazzle us with not one but four different gorgeous bridal outfits.

As the musical reaches its happy ending and he’s back to “real life,” Man in Chair wonders sadly why it can’t be more like the theater. The Drowsy Chaperone entertainingly makes the same point Preston Sturges made in his great 1941 movie about movies, Sullivan’s Travels: we need entertainment—comedy, music—to get us through life, as we stumble along.

Evelyn Rosenthal is a singer specializing in jazz and Brazilian music, a freelance editor, and the former editor in chief and head of publications at the Harvard Art Museums. She writes about musical theater and music for the Arts Fuse.