The Cast Photo by Brett Beiner Photography

My point is that Theo has more fun with its space than any other theatre company in town, and with a gloriously silly play like The Drowsy Chaperone, a 2006 musical-within-a-play satire of 1920s musicals with a score by Lisa Lambert and Greg Morrison and book by Bob Martin and Don McKellar, it has found new ways of inviting us in. Director L. Walter Stearns and his brilliant cast start with the premise that this entire musical is happening in the mind of McDonagh's musical-obsessed main character and that we are in his home as guests. As he explores with us his favorite old show, it explodes into life all around him and us, the actors tap dancing right up to us (at several points collapsing onto a settee inches from my face), entering the frame next to those seated at the bar, and generally having a great time and taking us along for the ride.

The plot of The Drowsy Chaperone (the play within the play) involves a universally loved Broadway star, Janet Van de Graff (Kelsey MacDonald), who has announced her retirement from the stage in order to marry. Her manager, Feldzieg (the always wonderful, perpetually harried Reginald Hemphill), about to lose his meal ticket and threatened by gangsters posing as pastry chefs if he does so (it's that kind of show), plots to undermine her plans and stop the marriage. Meanwhile, all around her, wedding guests fall randomly in love with each other. (It's that kind of show too.)

MacDonald is a ditzy delight as Janet, who has an early "I want" parody in which it's perfectly clear that she is fooling herself about this retirement–though she proclaims that she doesn't want to "Show Off" anymore, she utterly revels in doing so. (She also has an Act Two ballad, simply called "Bride's Lament," with lyrics so knowingly silly that Man in Chair tells us to ignore them, and she is somehow equally poignant and absurd.)

Her intended husband is Robert Martin (Trey Plutnicki), the kind of perfect man/empty shell that would make a great Disney prince. He is, in his own words, an "Accident Waiting to Happen" as he and Janet stumble toward a marriage based on one fine conversation. Think Anna and Hans in Frozen. Unlike that icy couple, though, Robert and Janet actually do love each other in their own ridiculous ways, though his relationship with his best man, George (Kevin Chlapecka, here constantly on edge because he is also the wedding planner), is closer, and their tap dance scene is a showstopper.

Other main characters (all introduced in a whirlwind number called "Fancy Dress") include the titular Drowsy Chaperone (Collette Todd, both drowsy and tipsy, despite Prohibition, and having more fun than anyone, especially with her own ballad "As We Stumble Along"); the doddering socialite Mrs. Tottendale (Jenny Rudnick), who cannot ever remember why she is wearing her fancy dress (a wonderfully ridiculous concoction by Nick Cochran, whose costumes are impeccable as well as imaginative); her put-upon servant, whom she calls Underling (played with stoic humor by Peter Ruger); the buffoonish love machine Aldolpho (Darian Goulding, having perhaps as much fun as Todd); the aforementioned gangster/pastry chefs (Jimmy Hogan and Chase Wheaton-Werle); Kitty (Luiza Vitucci), the self-absorbed and self-deceived talentless hopeful heir to Janet's film fame; and (one of my favorite names of all time) Trix the Aviatrix (Lena Simone).

As silly as the musical's antics are (pretty much every character is a parody of the kinds of stereotypes that once were typical in such shows), this show is really about Man in Chair. He is a lonely man who shuts himself up in his record-filled apartment, living through his musicals, about which he knows everything including the kind of details that only a totally obsessed fan knows. When he is listening to this one along with the audience, he comes alive, wandering through the choreography, singing along at times, emotionally entranced with every moment. When something happens that he judges to be wrong for the character or scene, his criticism is harsh but his love for the show never wavers, and introducing it to a new audience is clearly the main pleasure of his life. McDonagh infuses him with such joy and pathos that it's impossible not to love him, and we feel the importance of the moment with him when he finally walks out the door at the end to connect to the real world, though we know he's probably singing his cast recordings quietly as he does so.

Stearns (along with his gifted choreographer Jenna Shoppe) makes both of the worlds of this play shine. Man in Chair may be a shut-in, but he's a likable one, and his inner world is magically alive in his joy and enthusiasm as well as his imagination. Stearns blends the "real" world, the "musical" world, and the audience's world so well that sometimes it's hard to know where one begins and the others end, and we're all better off for it. Bob Knuth's set design provides a space for everything and allows us to understand this man even before the show starts. Ellie Fey's lighting and Anna Jackson's sound could not be more perfect. And Eugene Dizon and his small band simulate the sound of a much bigger orchestra.

This play is simply a joy and Theo is always an unforgettable experience. No one who love musicals should miss it.

The Drowsy Chaperone runs through April 19, 2026, at Theo Ubique, 721 Howard Street, Chicago IL. For tickets and information, please visit theo-u.com.