Deep Dive: THE DROWSY CHAPERONE
The Show That Started as a Joke
(Photo by Sara Krulwich)
The Drowsy Chaperone wasn’t supposed to be a Broadway musical. It was meant to be a party trick. Literally. Canadian writer/comedian Bob Martin didn’t want strippers at his bachelor party, so his friends wrote him a 30-minute pastiche of a fake 1920s musical. Martin loved it and joined on as a second librettist and that goofy little parody became a Fringe hit, then a Mirvish hit, then an Ahmanson hit—and suddenly Broadway had The Drowsy Chaperone, starring Bob himself as the fussy, cardigan-wrapped “Man in Chair.”
A nearly two-year run, 5 Tony Awards, a national tour, and countless productions all over the world later…Drowsy’s origin story that proves sometimes “a stupid little inside joke with your friends” really can change your life.
The Sutton Foster Era
One person whose life was forever changed by The Drowsy Chaperone was its leading lady Sutton Foster. Now, let’s be clear: Sutton Foster became a star in Thoroughly Modern Millie. Her breakout, Tony-winning performance made her the girl to watch, but only for audiences. Critics were less enthused by her, especially Ben Brantley at the New York Times, who found her “grating” in Millie and dismissed her follow-up, Little Women, entirely. The narrative was, “Sure, she’s talented, but is she really a Broadway leading lady?”
Enter The Drowsy Chaperone. As Janet Van de Graaff, Sutton had the best of both worlds: a role big enough to show off her triple-threat chops, but inside a genuine ensemble comedy where she wasn’t carrying the whole thing on her back. And suddenly, every critic including Brantley bent. That shift mattered.
Drowsy was the moment the critical establishment stopped treating Foster like a lucky understudy who stumbled into stardom, and started recognizing her as a bona fide Broadway leading lady with staying power. From here on out, Sutton Foster wasn’t going anywhere. She was no longer the “Millie girl”—she was the real deal, and critics finally had to admit it.
A Musical in Footnotes
The genius of Drowsy isn’t the fictional musical-within-the-musical (which is intentionally dumb and cocaine-fueled in its 1920s pastiche way). It’s the Man in Chair. An ordinary man who, while Drowsy Chaperone plays out before us, guides us through it all by providing us with fun facts about the performers, the time period, as well as his opinions about the wit of the songs and the ridiculousness of plot points. And he does it all with love. He’s not just a fan of The Drowsy Chaperone, he’s its translator. An obsessive who can’t help footnoting every line. Without him, Drowsy is just a spoof with some catchy tunes. With him, it becomes a show about what it means to love theater so much you defend it past the point of reason.
And honestly? I get it. Because the Man in Chair is us.
Nostalgia, Earnestness, and Why It Still Matters
I always come back to this: musicals are inherently earnest. Even the most cynical ones can’t help but show their heart. That’s why the Heathers musical will never hit like the Heathers movie. You can’t sing through pure cynicism. You break eventually.
Drowsy knows this. The show within the show is dumb as hell. But the frame—the Man in Chair defending it to us, trying to convince us of its worth even as he admits its flaws—that is heartbreakingly human. Because loving musicals is messy. They’re outdated, problematic, ridiculous. And we still love them. We love them because they comfort us, because they remind us of our parents, our high school obsessions, our first cast albums. Because even when they’re bad, they’re ours.
And sometimes, like Man in Chair, we put on the record again and again, hoping this time it will give us an answer it can’t possibly provide.
For this Deep Dive episode, I got to sit down with Eli Rallo—author of the new book Does Anyone Else Feel This Way—and pull apart the lore, the history, the guts of a show that shaped theater forever. This is just a taste. If you want the full ride, listen to the full episode of Broadway Breakdown HERE
And hey, subscribe to the Substack, follow me on socials ( @mattkoplik), and join the congregation. Together, we can all stumble along!