The third season of Netflix’s I Think You Should Leave includes a sketch where two men wear the same shirt to a fourth-grade choir concert. The men, played by series co-creator Tim Robinson and scene-stealing guest star Biff Wiff, laugh off the minor awkwardness when Wiff calls Robinson his “shirt brother.” In typical ITYSL fashion, things go off the rails from there. Wiff stares at Robinson with a demented grin during the recital, then disappears. When he returns, it’s to ask his shirt brother for help: “I’m in deep fuckin’ trouble here,” he says, the desperation written in the creases on his forehead. The trouble is he’s trashed a classroom while in a kind of pop-punk-induced trance. “I’ve been listening to this new song by this band I’d never heard before, and they’re saying there’s no rules,” Wiff explains. “Do you think that’s true?”
The song that causes Wiff to question all authority is “Listening,” by a band called the Everything-You-Knows — now revealed to be the Baltimore melodic hardcore mainstays Turnstile. “Everything you know/ It’s all just for show/ I don’t wanna go on listening,” goes the song’s apparently mind-unshackling chorus. Wiff is in his 60s, but the sentiment hits his character like he’s still 13. He sends Robinson back into the recital so he can catch his daughter’s solo. “It’s too late for me,” he says, staying behind in the destroyed classroom. “I’m awake now.”
Wiff’s “shirt brother” is part of a rich tapestry of ITYSL characters who are obsessed with society’s rules, and who go to ridiculous ends to either uphold or undermine them. But he also belongs to a second subcategory of ITYSL character, one that hasn’t been analyzed nearly as much. He’s a music guy. A magical, eye-opening song comes on, and he starts runnin’ around, goin’ nuts, movin’ his head all around. Across three seasons and 85 sketches, Robinson and co-creator Zach Kanin have loosed dozens of music guys (and yes, they’re all guys) into their chaotic universe. They’re a diverse cohort, ranging from skilled musicians to wide-eyed superfans to hangers-on at the industry’s darkest fringes. Herbie Hancock (not played by Herbie Hancock) even makes an appearance. The specifics of all these guys’ stories suggest that Robinson and Kanin, too, are music guys.
Tim Robinson is famously media-shy, rarely giving interviews and remaining deliberately impenetrable whenever he does, so it shouldn’t come as a shock that he’s never really talked publicly about music. (We do know for a fact that he’s a Turnstile fan.) But the way he and his writers subtly lampoon music culture feels like a secret handshake. Even including a song by Turnstile — by no means a cult band anymore, but not world-dominating superstars either — plays like an offering to, well, the kinds of people who read this website. Christian Lee Hutson wrote the song “Is This It” for Season 3’s Sitcom Taping sketch. In Season 2’s sketch about a guy who used to be a piece of shit, an Auto-Tuned but still unmistakable Ezra Koenig sings a ridiculous song called “Dangerous Knife (The Night Is A Knife).” The song is half-audible, playing behind a montage of men with slicked-back hair dumping water on steaks. It could have been anybody. Robinson wanted Koenig.
It’s through the characters themselves that ITYSL‘s music-guy sensibility is most thoroughly felt. A few only exist offscreen but still feel fully realized: the shredder Slish Valdez, credited with something called “ramp guitar” on a dating-show montage; Jeff Chris from Indiana, a professional mixer who’s gonna fly down and get this thing really popping off; jazz legends Marcus “The Worm” Hicks, Roy Donk, and Paul Bufano. I can picture every single one of these guys in my head, and I suspect Robinson and Kanin can, too.
The next level of ITYSL music guy lives at the borderlands of the music world and is itching to get inside. There’s the Driving Crooner, a Robinson-portrayed motorist with decals on his car windows that make it look he’s wearing a top hat and smoking a cigar. The Driving Crooner “wants to make money from it so bad,” but he hasn’t figured out how — a streaming-era refrain that should resonate deeply with anyone in a band. Another struggling character is Don Bon Darley, the onetime King Of The Dirty Songs. There’s not much demand these days for his vulgar drinking songs, and he can’t remember the words to them, anyway. He’s stuck on the outside looking in, performing at a 40th birthday party that’s clearly his first engagement in a long time. In one of the show’s most famous sketches, a country group recreates the Sun Records scene from Walk The Line. Gospel ain’t sellin’, so they try out an original: the stark, gothic “The Day Robert Palins Murdered Me.” Robinson’s bass player — who isn’t named Billy — has trouble following frontman Billy’s lead, taking bizarre detours into a song about how bones are the skeletons’ money. He’s still confident the band will get signed; I’m not so sure.
Another Robinson character is signed, to Robbie Starr’s Superstar Tracks Records. Unfortunately, even though he thought his song was going to be a hit, it turns out it fucking sucks. Starr (Conner O’Malley) runs a predatory, pay-for-play operation that targets “old guys at the mall” and persuades them to come record at his dingy studio. What we hear of Robinson (and another old guy named Johnny) suggests that their songs were never going to be hits, in the ITYSL universe or any other. But Starr convinces his proteges that with a few more dollars, he can totally help them break through. The sketch is funny, but at its core is a heart-wrenching truth. There are way too many Robbie Starrs in the music industry, at all levels. The rot runs deep, and Robinson leans into that darkness like someone who has seen it up close. (It’s worth mentioning that this all unfolds in the context of a commercial parody about a minimally invasive spinal surgery. Sometimes I forget that ITYSL is not a normal show.)
A level up from these guys are the musicians who actually show a little talent but deploy it in hilariously inappropriate situations — namely, funerals. In a sketch that mostly consists of Robinson being stalked by an unhinged Conner O’Malley character who sees his “Honk If You’re Horny” bumper sticker, he winds up singing an a cappella pop ballad at his mom’s interment. (Sing it with me: “Friday night/ I’m thinking that we just might/ Fly away to someplace they don’t know who we are.”) “Friday Night” is way too good to be a throwaway joke, and Rolling Stone’s Rob Sheffield may have had the final word on it when he unironically included it in his list of the best songs of 2019: “It’s not even a parody — it’s too delicate for that. It makes me feel something; it makes me feel like an idiot for feeling something; it plays in my head when I’m trying to concentrate on something more important. Isn’t that what pop music is all about?”
New Joe, a fill-in church organist portrayed by the late Fred Willard, is the “Friday Night” guy’s even more chaotic counterpart. He deeply, earnestly believes that he’s playing a somber, funeral-appropriate hymn when he fires up “He Layeth On High.” (He does concede that it’s about a big baby duck that gets its head caught in a stewed tomato.) He bows his head, offers his condolences, and proceeds to play a honking, whirring tune on an enormous American Fotoplayer, smashing plates for percussion. Maybe he could have had a vaudeville duo act back in the day with Don Bon Darley, but like most ITYSL protagonists, he can’t function in our world. Yet every antique musical instrument collector’s convention has a few New Joes, who can totally rip on the Fotoplayer and would love to prove it at a funeral.
The most recognizable – and therefore the most excruciating – ITYSL music guys are the fans. They’re typified by two men who take their enthusiasm for their favorite musicians to self-destructive (but fundamentally opposite) levels. The first is a starstruck Robinson character who tries to avoid embarrassment in front of Caleb Went, a musician and fashion designer whose work he loves. He ends up nearly choking to death. The other is Howie, a ponytailed Tim Heidecker creation who serves as the final boss of ITYSL music guys. Howie is unbearable. He imposes on his hosts, farts in mixed company, and terrorizes his doting girlfriend. But worse than any of that, Howie is a jazz guy.
The setup of the “Game Night” sketch is a group of friends getting together for a round of 20 Questions. The first two celebrity names go off without a hitch — George Clooney and Julia Roberts, both easily guessed. Then Howie’s names start showing up. Amid a reign of social terror that swallows up everyone at the party, he introduces us to jazz greats like Thaddeus Finks, Mookie Kramer, Jack Marshall, Tiny Boop Squig Shorterly, and Paul Julian. Some of those names are real; some are inventions. Howie grows increasingly exasperated when the philistines in the room don’t know any of them. If you’ve never met a jazz guy like Howie, pray you never do. Robinson, Kanin, and Heidecker clearly have.
Music is a major part of basically every sketch show ever made. It predates sketch shows, in fact, stretching back to the variety shows of the early television era and to vaudeville before them. But no sketch show (apart from maybe Portlandia) has ever made me, a person who moves in musical circles, feel more seen than ITYSL. Some of the music guys of ITYSL are malevolent and some are well-meaning, but they’re all very slight amplifications of very real people — people who, if you love music and engage with its subcultures, you probably know. But don’t worry about the music guys. They’re awake now.