Jason Alexander is no stranger to the stage. He made his Broadway acting debut in 1981 at the tender age of 22 in Stephen Sondheim and George Furth’s famous (or infamous, depending on who you ask) Merrily We Roll Along. More than four decades later, the musical is poised to make a Broadway return this fall, in a new revival led by Daniel Radcliffe, Jonathan Groff, and Lindsay Mendez at the Hudson Theatre beginning September 19.

On the other side of Broadway, at the Hayes, Alexander is already making his debut as a Broadway director with the Main Stem's newest farce, The Cottage. With that production set to continue through October 29, Alexander's latest career achievement will be running alongside the first Broadway revival of his first Broadway show for a little over a month. It's an unlikely full-circle coincidence for Alexander—but between mastering Sondheim's rhythms and expertly landing punchlines for nine seasons of Seinfeld, his career has always been built on good timing.

“I think we’re all excited about it, if for no other reason because we always loved the show,” says Alexander about Merrily's upcoming revival. “We thought the show got kicked around more than it deserved.”

The musical famously capped a decade-long string of groundbreaking, genre-defining musicals with scores by Sondheim and direction by Hal Prince. From Company to Follies, A Little Night Music, Pacific Overtures, and Sweeney Todd—the pair singlehandedly created the post-Rodgers and Hammerstein era on Broadway, challenging what musicals could be and how they could tell their stories.

But Merrily ended that streak of Tony-winning artistic successes. With a cast of teenagers and 20-somethings playing characters from high school graduation through to bitter mid-life crises (in a story of friendship told in reverse), many found the original production to be a jumbled mess. It would only run for 52 previews and 16 performances. Sondheim and Prince wouldn’t collaborate again until more than two decades later on Bounce, a project that was also a critical and commercial failure.

“We realized then that we were asking the audience to understand a lot,” explains Alexander of that original production. “Kids playing adults, the thing going backwards, the hero not being a hero at all when you first meet him. And then trying to find a way to embrace him to that you can feel the loss of his potential by the end of the play. That was a lot to ask an audience.”

But back to that good timing. Forty-two years later, Alexander says everything is different for Merrily. “The audience now knows what they're in for. And not only do they know it, they're waiting for it. It's like finally seeing [Sondheim and Prince] get some of the due they should have had all those years ago. It's a bittersweet thing for us.” 

But it’s not just different for the audience. Himself 42 years older, Alexander says he understands the piece differently now. “I understand more of what Hal, Steve, and George were going for,” he says. “When I was a kid, I didn’t quite feel their exploration of the loss of potential, the loss of opportunity. The tragedy of the show was not quite knowable to me when I was 22. I get it more now.”

That change didn’t happen by accident. Alexander has seen a lot in the intervening years—a period that saw him win a Tony Award for his work in 1989’s Jerome Robbins' Broadway, and shooting to international stardom the same year on TV’s Seinfeld, in which Alexander played George Costanza for nine seasons and earned seven Primetime Emmy Award nominations. With the financial freedom that comes with starring on a megahit sitcom, Alexander has never strayed too far away from the stage, appearing on Broadway in Accomplice and Fish in the Dark, overseeing several productions with LA Reprise! (the West Coast equivalent of New York City Center Encores!), and acting in the national tour of The Producers. He’s also starred in several stage-adjacent screen projects, like TV movies of Bye Bye Birdie, Cinderella, and A Christmas Carol; and a feature film adaptation of Lucky Stiff, among other projects.

Alexander says the stage has always been his first love, his first dream—and Seinfeld actually fell right into that. “That show felt like a theatre piece,” he says. “Every week, we were just playing to our live audience. We trusted and believed that the cameras and the director were getting the performance that we were giving to the audience.”

The experience also let Alexander spend nine years honing and fine-tuning his comedic muscles. After 171 episodes, the actor knows a thing or two about how to land a joke. Perhaps unsurprisingly, the musical theatre alum thinks of it as a kind of music. “What I have found in good comedic writing from many different writers is they tend to have a music in their head with they’re writing,” he explains. “Neil Simon had his own sense of music, John Shanley has his own sense of music, Larry David has his own sense of music. And when you latch into the music in the author’s head, it becomes easy.”

Alexander has spoken not infrequently about his process finding the music of Seinfeld. When he first began the show, he saw George Costanza as a Woody Allen type. Once he figured out Costanza was more or less a stand-in for series co-creator and head writer Larry David, he was able to unlock the character’s full comedic potential.

And now Alexander is bringing that sense of comedy back to Broadway, this time in the director’s chair. He's been working with Clue playwright Sandy Rustin on The Cottage for few years now through a series of workshops and readings that culminated with an opening night on Broadway July 24. With all that comedy “music” in the air, Alexander thinks of the show like a “non-musical musical.” 

Rustin has channeled the upper-crust British humor of Noël Coward, finding laughs placing sexual impropriety hand-in-hand with the proper manners of 1920s British society types. The story is set off by a woman who reveals her extramarital affair to both her husband and her lover’s wife, both of whom arrive in short order at the scene of their partners’ latest tryst. You could be excused for thinking this was an episode description from The Jerry Springer Show. But in The Cottage, the events play out with less chairs being thrown than there is tea poured. “The Brits have this very refined demeanor while doing very unrefined things,” Alexander says. “And that juxtaposition sometimes can be very, very funny.”

When Alexander spoke with Playbill, he was still in the middle of technical rehearsals for The Cottage. Alexander has been spending much of the rehearsal process focused on finding the rhythm of the play, whether it’s the characters’ exhaustive penchant for repeated use of the word “darling” or even seemingly simple staging decisions. “We work to find the rhythm of somebody’s entrance, when a door slams. Is it step, step, step, slam? Or is it step, step, step, step, slam? You have to have an innate sensibility about which one is going to be funnier.”

Luckily, The Cottage has got comedy chops on all sides of the curtain. Alexander has assembled an all-star cast of comedy experts, including TV stars Eric McCormack (Will & Grace) and Alex Moffat (SNL), Legally Blonde star Laura Bell Bundy in a triumphant return to Broadway, Tony nominee Lilli Cooper, Nehal Joshi, and Dana Steingold. “When it’s a matter of timing, good comedic actors know. They know in a big laugh when is the perfect moment to start the next line so that you don’t lose the momentum. It is just this unknown, unspoken, unteachable thing.”

According to Alexander, this cast has it in spades. “As Dennis Miller says, it’s called a sense of humor, not a science. You either have that, which allows you to hear the possibilities of these rhythms and this musicality, or you don’t.”

This unteachable understanding of comedy makes it vitally important that performers are synchronized with the music of the writing, which also means that neither can necessarily fly on their own. “Take a famous piece of comedic material, like the ‘Who’s on First’ routine,” explains Alexander. “Look at it printed out on a page. There’s nothing there. There’s no funny. The minute you hear [Abbott and Costello] start to put the rhythm and the melody on it, it becomes hysterical. There’s a magic in it.”

He says the same was true of even Seinfeld scripts. “When they were writing for, say, Jerry Stiller, they wrote the line, ‘Are you telling me there’s not one condo available in all of Del Boca Vista?’ That’s not a joke. But when Jerry says it apoplectically, it becomes radically funny. Writer and performer knew they were singing the same songs.”

The project is Alexander’s first time directing on Broadway, though not his first time directing. Over the run of Seinfeld, he directed three episodes. Since then, he’s directed episodes of Campus Ladies, Everybody Hates Chris, Criminal Minds, ‘Til Death, Franklin & Bash, Mike & Molly, and Young Sheldon. For the stage, he’s directed productions of Sunday in the Park With George, Damn Yankees, and The Fantasticks. “I've always loved looking at the big picture of things I was working on, and seeing how the pieces came together,” says Alexander. “You're engaged in many, many more capacities than when I'm just the actor.”

He also says The Cottage is fulfilling a lifelong dream, which has been a theme throughout his career. According to Alexander, all his Broadway aspirations felt like a fantasy that he might achieve by his 40s or 50s if he was lucky—until he ended up making his Broadway debut at 22 and winning a Tony Award at 29. Directing The Cottage is itself the result of some fortunate happenstance—Rustin and Alexander once shared a talent agency, which happened to connect them on the project.

“For whatever reason, this disproportionately blessed career that I’ve had keeps giving me the thing I dream about next. I honestly don’t know what to dream of next," says Alexander, pausing briefly before adding with—what else?—impeccable timing: "but I'll think of something."

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