Grapetooth Are the Last Fun Band Standing

The Chicago duo has been selling out venues for the last year. We caught up with them on the cusp of their debut LP.

There is a new look that is ready to sweep the nation. It is called the “Hat Nine,” and Grapetooth is here to make you a believer.

"It came about when I walked out onto the porch one day earlier this year, and found Clay giving himself a haircut with clippers in a mirror with tiger print on it,” explains Chris Bailoni, one of the band’s two members. “That night, when we came home from Rainbo Club, [we] did the first Hat Nines to each other. It’s basically just a bowl cut, but it has to be done with the official hat and clippers with the ‘nine’ setting on. So far there are seven of us, I believe, so only a couple more can be done to be an O.G. member."


The Hat Nine is modeled with some dishevelment by both halves of Grapetooth, Bailoni and Clay Frankel, who share duties singing and toying with synths and drum machines.“We gave out two or three Hat Nines at our last show.” The venue staff was less than hyped, he says, but that’s rock and roll for ya.

Longtime pals and current roommates, the two also happen to be in the most fun band in Chicago. Exhibit A: “Trouble,” a song with a wheezing, drunken synth line that teeters on the brink of chaos and makes me feel like John Lennon in that goofy street-dancing photo. In the video for the track, Frankel and Bailoni terrorize Chicago by moped and with loose-limbed, hand-clappy dance moves, viewed through skate-vid fish-eye and accompanied by scrawled sketches of anthropomorphic wine glasses smoking cigs. If you aren’t smiling by the time the sing-shouted chorus hits— “I don’t mind livin’! I don’t mind givin’ it up!”—there’s a decent chance you suck.

Exhibit B: the footage from the duo’s first-ever NYC show, which they’re gearing up for during our interview in late September, and which sold out almost immediately despite the band having released a grand total of three songs at the time. Frankel and Bailoni are joined onstage by what looks like half the audience, shouting along to every word as a bottle of wine gets passed around. Everyone looks totally ecstatic.

Watch the video premiere for Grapetooth's "Blood."


We’re sitting in a cozy booth in the aforementioned Rainbo Club, the notorious Ukrainian Village dive frequented, over the last 80 or so years, by Nelson Algren, Liz Phair, and almost a century’s worth of of local delinquents, present company included. When I ask him how Grapetooth became beloved by so many so fast, Frankel’s answer is simple. “Have you seen this guy dance?” he says, gesturing with a grin towards his bandmate over a PBR tallboy. “That’s worth the price of admission right there!”

If you’ve been paying the slightest attention to the Chicago scene in the 2010s, you already know Frankel from Twin Peaks, the homegrown garage-rock heroes known for their rowdy live shows. And perhaps you know Bailoni as Home-sick, the producer behind dreamy bedroom jams like last year’s “Your Body,” featuring high school homie and singer-producer Knox Fortune. But Grapetooth’s music sounds very little like either of the above; nor do they sound like anything else coming out of the city right now. In other words, this ain’t your average @ChicagoBandBoy (even if that highly accurate parody account’s bio reads, “i saw twin peaks at a house show in 2011”).


Instead, Grapetooth sounds like a scuzzed-up version of the bands they first bonded over when they met in 2012: New Order, Arthur Russell, the Japanese psych-pop group Fishmans. Most of all, they obsessed over Yellow Magic Orchestra and the Tokyo electronic group’s solo offshoots—especially Yukihiro Takahashi, who’s become something of a hero to the duo. In 2015, years before they decided to release anything or play live, that shared sense of discovery inspired the pair to start working on songs in Bailoni’s synth-filled bedroom studio. It wasn’t until Knox Fortune talked them into opening his record release show last winter that they figured they might as well make the collaboration official.


“My buddy called me ‘grapetooth’ one time when my teeth were all red from drinking wine. It immediately fit the vibe of the music Chris and I were making.” —Clay Frankel

And thus, Grapetooth was born, introducing the world to an immediately crucial term for a wino. “My buddy called me ‘grapetooth’ one time when my teeth were all red from drinking wine,” explains Frankel. “It immediately fit the vibe of the music Chris and I were making.” The name definitely tracks: Grapetooth’s music is the perfect soundtrack for splitting a jug of Carlo Rossi, dancing til 5AM, and waking up on your friend’s couch clutching a half-eaten burrito and cursing whichever deity invented sunlight. (Your mileage may vary.) It’s that element of joy that, more than anything, ties Grapetooth to Yellow Magic Orchestra—a group that showed the world that music made with synthesizers and drum machines could be brimming with humanity, presenting electronics as free-spirited and a little manic, rather than dystopian and dark.

But Grapetooth’s spirit of reckless abandon lends itself to some seriously gorgeous melodies: “Red Wine,” a ballad narrated by a lovable fuck-up, sees the duo’s voices drowning in layers of dreamy synths, and on “Violent,” they channel New Order at that band’s most anthemic. The clip for the latter draws inspiration from Terrence Malick’s Badlands, reimagining the film’s South Dakota killing spree as a Logan Square dirtbag heist set at their old apartment, where, they say, their former landlord has suggested they were responsible for thousands of dollars worth of damage. “Imagined damage,” Bailoni stresses. “I love that band,” Frankel quips.


Badlands aside, the band has a strict anti-narrative policy: “Nothing linear, nothing should make sense,” says Bailoni, who edits all of Grapetooth’s videos himself, in addition to hand-drawing their insanely sick single artwork. “We try to avoid any sort of beginning, middle, or end.” (For what it’s worth, Arthur Russell shared almost this exact sentiment in defense of disco in an 87 interview.)

That aversion to all things linear extends to their self-titled debut album, which is out November 9 and a contender for one of the best Chicago releases of the year. Party anthems sit alongside doomy synth ballads about death—and that’s before you get to “Together,” a Kris Kristofferson-style drinkin’ anthem sung by Frankel and Bailoni in twangy unison and punctuated by wild whoops and yee-haws. And then there’s “Hangover Square,” a jangly New Romantic jam whose lyrics were inspired by a 17th century poem, penned by one Sir John Suckling, that Frankel found in the preface of a book in their apartment by the same title. “The poem completely fit the melody we already had in mind,” says Frankel. “It’s cool—it has words like ‘prithee.’”


None of it should make sense, but somehow, it works. “The way we make music, there wasn’t any overarching scheme or mold,” Frankel explains. “It’s almost like the song you’re writing right then is the first song you’ve ever written.” Bailoni agrees: “We don’t sweat too much if things are a little off-kilter—that’s our style, to be honest,” he says. “I mean, our bread-and-butter keyboard sound is really warbly and kind of silly, and out of tune a little bit, from an old Yamaha synth I found in an alley.”


More than anything, it’s Bailoni and Frankel’s camaraderie that ties together the band’s sprawl of sounds. Having lived with Frankel for three years now, Bailoni’s gotten accustomed to his bandmate wandering into his room in the morning with a half-formed hook ready to go. There’s an obvious mutual admiration between the two: “Chris is completely fearless, musically,” Frankel tells me when Bailoni is out of earshot. “He has a very weird musical brain—completely unorthodox in the way he plays instruments, but very technical-minded as a producer. There would be nothing without that guy.”

And though he’d never played live before Grapetooth’s first show, Bailoni does have a bit of performance experience: for years, he worked at haunted houses all over the Chicago suburbs, eventually creating his own deeply strange character. “I had this oversized straightjacket with these bloody, ripped-up pants, and these big ol’ serial killer boots,” he explains. “Then I made a professional, old Hollywood-style sock mask—this bandaged-up latex thing [where] I ripped up the eyes. The mouth was shut, but it had huge amounts of twine and string wrapped all around it. When I moved my head, it was like this big blob of mess that was very weird to look at. It was very ambiguous, so it was very fun.”


Yes, there are photos, and yes, it’s possible to detect traces of Bailoni’s haunted house days in Grapetooth’s live shows. “My cousin told me that they saw a video of me on stage at Lollapalooza for a song with [Knox Fortune],” he says a bit sheepishly. “I had this strange, jerky motion that I didn’t realize is what I actually look like on the stage. At the haunted house, they wanted very quick, startling movements. So that’s bled over into this… I sound like I’m insane.”

Knowing this strange footnote in Bailoni’s life story, you might expect “Blood”—the latest and, from where I’m standing, best single from the record—to be a bit gory and gothic. Instead, it’s pure new wave bliss, the kind of song that could soundtrack a prom scene in an 80s coming-of-age drama. Pop a bottle of your finest Sutter Home, have your roommate bust out the clippers for a DIY Hat Nine, and get ready to dance your ass off. Meaghan Garvey is a writer based in Chicago. Follow her on Twitter. Brittany Sowacke is a photographer based in Chicago. Follow her on Instagram.