How Documentary Now! captured John Mulaney’s cheerfully whacked vision of Broadway

Of the teeming glut of anthology shows currently dominating television, few are as ambitious in their nuts-and-bolts details as Documentary Now! Sure, Black Mirror swaps in a new cast every episode, and each season American Horror Story finds a fresh way to traumatize its fans with the specter of a gleeful, murderous Kathy Bates. But the producers, directors, writers, and staff on IFC’s comedic homage to documentary filmmaking don’t just have to swap genres from week to week; they’ve got to do it while also mimicking the look and styles of some of the most beloved nonfiction films in history. So, hey, why not take that delicate tightrope act and throw in the creation of an original, six-song faux-Broadway musical while they’re at it?

As the second episode of Documentary Now!’s third season, “Original Cast Album: Co-op” has big shoes to fill from pretty much every direction. It follows up on a two-part premiere that featured A-list stars like Owen Wilson and Michael Keaton, and in the footsteps of the show’s previous big musical swings like “Final Transmission” and “Gentle & Soft.” On the episode’s set last fall, though—in a small performance-arts space at an Oregon community college, filled with much of the same crew that cut their teeth on IFC’s Portlandia—there was no sense of that pressure from the star-studded cast. They mostly just looked like they were having a hell of a lot of fun, delighting in the absurdist Sondheim sound-alikes penned by Late Night and Documentary Now! co-creator Seth Meyers and the episode’s architect, comedian (and unabashed theater nerd) John Mulaney.

Mulaney wasn’t on set for the day of the A.V. Club’s visit (and was unavailable to be interviewed for this article), but his love of Sondheim, and of the episode’s primary inspiration, D.A. Pennebaker’s 1970 Original Cast Album: Company, was in clear evidence. You could hear it in a conversation with the episode’s standout performers, A.P. Bio’s Paula Pell and Broadway/TV star Richard Kind, which drifted rapidly from Kind’s past experiences with the real Sondheim—of whom Mulaney’s Simon Sawyer is an affectionate, tongue-in-cheek impression—to praise for the writer and comedian’s elaborate attention to detail. Kind was exactly as garrulous as you might expect from his roles on shows like Mad About You or Spin City, with no evidence of the shortness of breath that provides the central joke of his big breakout number, the fast-paced patter song “Christmas Tips.”

“What’s crazy is, I know about 40 percent of the people in that movie,” Kind said, referring to the original documentary, while praising both Mulaney’s kindness and his fixation on the film’s small details. “I saw the original Company, I saw [Elaine] Stritch do it, I remember those sets. It’s crazy how good this is. It’s unbelievable.”

Meanwhile, co-star Alex Brightman, best known for the Broadway adaptation of School Of Rock, is no less quick to heap praise on Kind, who’s been performing “Christmas Tips” on the late-night circuit ahead of the episode’s debut. “We just watched him crank out his song, five times, back to back to back,” Brightman said with admiration. “We got to sit back because of how it’s being shot, but he’s basically singing it a cappella. There should have been a fourth camera shooting just the silent room with him screaming in it.” Kind’s response: “Oh, that must have been a horror.”

Talk shifted to the original doc, a favorite among this particular set. “[‘Co-op’] actually has a little more narrative,” Brightman noted, comparing Pennebaker’s fly-on-the-wall film and Doc Now!’s stylistic recreation. “And I only really say that because the original has zero narrative.”

In fact, Meyers made it clear that he and Mulaney found Pennebaker’s original movie so light on story that they had to crib one from another Sondheim doc in order to flesh things outs: 2016’s Best Worst Thing That Ever Could Have Happened, about the troubled production of 1981’s Merrily We Roll Along. That infamous flop at least made it to 16 performances; the fictional Co-op closes after a single night, forcing the cast to record their album in the wake of the dismal news. “That’s where the show’s sketch-writing roots come in,” Meyers later added, by phone. “In finding that turn, so that you’re not just presenting an exact copy of what’s come before.”

In fact, he and Mulaney wrote a ton of additional material that didn’t make it into the episode, which, like every episode of Documentary Now!, has to wrestle with its mandate to adapt and parody much longer works into a 22-minute format. (At a scant 52 minutes, Company is one of their shortest pieces of source material.) “There was quite a bit more narrative that Mulaney wrote that was very funny,” director Alex Buono said. “Mulaney being Mulaney, he just wrote a really funny, specific, and narratively driven set of songs, plus a narrative beyond it that we were really not expecting.” (On set, one could see hints of at least one plotline, about preferential treatment for Brightman’s young up-and-comer, that didn’t make it into the episode itself.) Instead, the directors had to drill into the series’ mission statement: “Let’s create, using the Company format, a musical that’s just total nonsense,” which nevertheless also worked as an enjoyable series of songs and a recognizable riff on Company itself.

For that, Mulaney—who wrote most of the episode’s lyrics—worked with someone well-acquainted with TV parodies of popular stage musicals: occasional Sesame Street composer Eli Bolin, whose past credits include adapting Les Misérables for the singular talents of Cookie Monster.

Bolin broke down the writing process for an intentionally failed musical: “The pitch was to make the songs themselves as strong as possible, but the ideas for them are kind of awkward. Our goal is to make the best version of that bad idea.” The word that Bolin—who wrote the music remotely with Mulaney, sending lyrics and tracks back and forth digitally while Mulaney was on a stand-up tour—keeps returning to is “Sondheim-y.” Some of the songs in “Co-op” are designed to directly mimic tracks from Company—Pell’s big number, the scheduling-conflict-heavy “I Gotta Go,” is a direct riff on Stritch’s struggles with her big final number, “The Ladies Who Lunch”—but many of them are built around capturing a particular Sondheim-adjacent sound. He also admits to letting some later influences slip in; the episode’s big closing number, “Going Up”—about an asshole kid who pushes all the buttons in an elevator, forcing the residents of the titular building to ride up to the roof in a glorious metaphor for something—also cribs from composers like Alan Menken. It’s an upsettingly effective earworm, too. Nothing this intentionally goofy should be so hard to get out of your head.

In its third season, Documentary Now! is in a period of rapid evolution, one that allows individual voices to take the lead in guiding which eclectic topics it opts to cover. “Co-op” is Mulaney to the max, to the point that, even in his absence, it is clear that it was his particular obsessions driving the show. The episode creates a window into the weird little alternative version of ’70s Broadway that lives in his head, from the set design, camera lenses, and costumes, to tiny touches like Sondheim’s fiddly fixation with particular pronunciations. (“Say ‘goodie.’ Say ‘bubbie.’”) All that, and it also has to feel simultaneously like a spot-on recreation of a failed musical and be eminently listenable for the audience at home. It’s a tall order, but that’s the particular Documentary Now! alchemy. Meyers is more modest when asked what they were trying to achieve: “Our goal was just that Sondheim would hear it and like it.”