Bob Odenkirk and David Cross in the video for Yo La Tengo's "Sugarcube"

As a teenager in the 1990s, I had two overarching career aspirations: to be a comedian and to play in a rock band. The fact that I suffered from crippling social anxiety and didn’t know a single guitar scale didn’t seem like a hindrance to either. The rising “alt” comics at the time—Janeane Garofalo, David Cross, Sarah Silverman, Patton Oswalt, Todd Barry—projected a sort of ironic aloofness that ran counter to the Evening At The Improv mugging I’d been raised on, suggesting it was possible to be both painfully introverted and famous. And even my clumsy fists could squeeze out a Pavement song. And I was, in my opinion, a better than average drummer.

More notably, these did not feel like mutually exclusive goals. While comics and musicians have shared stages since the days of vaudeville, and every rock star wants to be a comedian and vice versa, in the ’90s they felt inextricably linked. From my limited purview as a (mostly) pre-internet only child in the Texas suburbs, hearing Janeane Garofalo drop Weezer references in her specials or seeing David Cross wear a Superchunk shirt on Mr. Show was akin to witnessing proselytizers for a world of cool I’d only barely glimpsed through Spin and on 120 Minutes. I formulated a fantasy of one, uniform society of funny, sarcastic slackers who flitted between stand-up and indie rock interchangeably. It was a world I very much wanted to join.

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This fantasy reached its apex in April 1997, as the release of Yo La Tengo’s I Can Hear The Heart Beating As One brought with it the video for “Sugarcube,” a clip that distilled the slacker era’s reluctant stardom down to four gloriously deadpan minutes. Starring Cross, Bob Odenkirk, and John Ennis, it’s essentially a Mr. Show skit that just happens to have a Yo La Tengo soundtrack. In it, the band’s Ira Kaplan, Georgia Hubley, and James McNew are chastised by their record label head (Ennis) for turning in a typically diffident, shoegazing performance and are soon shipped off to “rock school.” Under the tutelage of Bob and David’s glammed-up rock instructors, they learn guitar bowing, hotel room trashing, Tolkien-inspired lyric writing, et al., until at last they’re ready to graduate and deliver another video—which turns out exactly the same. Still, Ennis loves it, proudly proclaiming it their first No. 1.

“Sugarcube” is a slight concept as videos go, but it’s filled with great, mostly improvised gags: Odenkirk’s spoken-word performance of Rush’s “Closer To The Heart”; Kaplan holding up a photo of a Jewfro-ed Lou Reed and taking an eraser to the head for it; “The Foghat Principle,” etc. These classic rock riffs may or may not be funny—or even understandable—to an audience 20 years later; they barely were to me back then. But the video felt like a hip, sardonic rejoinder to celebrity posturing and the very idea of making an effort, as was the style at the time. I spent probably half a day downloading the clip as an MPEG, where I watched it over and over again.

“It’s such a cliché from that time: The record label is making you do a video, and the band doesn’t want to do one,” Kaplan tells me. “But like a lot of clichés, I guess there’s some truth it in. So we were just looking for ways to kind of creatively deal with that tension.”

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That reluctance had underscored Yo La Tengo’s approach to videos ever since the clip for 1993’s “From A Motel 6,” where indie film director Hal Hartley, backed by a $50,000 budget from Matador Records’ new corporate benefactors at Atlantic, had helped the band orchestrate a long, dry joke, wherein they were filmed slowly setting up their equipment just in time to mime along to the guitar break, right before taking everything down again. Atlantic hated it. Or, as Kaplan diplomatically puts it, it was “met with some lack of appreciation from some people.”

The group’s next video, for 1995’s “Tom Courtenay,” can almost be seen as a direct response: It opens with the cigar-puffing, sunglasses-wearing booking agent Bobby Romeo (still listed on Matador’s Facebook page, by the way) offering the band a gig opening for the reunited Beatles, leading them on a Hard Day’s Night-inspired montage of trying on outfits, traversing through screaming crowds, hanging backstage with Marshall Crenshaw, and, finally, disappointing thousands of Beatlemaniacs. In its use of narrative and its sarcastic rock ’n’ roll fantasy—and its cameo from comedian and future Best Show host Tom Scharpling—“there’s no question that was a big inspiration on the ‘Sugarcube’ video,” Kaplan says.

Both “Sugarcube” and “Tom Courtenay” were directed by Phil Morrison, a longtime friend—and occasional roadie—who’d been with the band since ’86. Morrison had also helmed the relatively straightforward clip for 1990’s “The Summer” prior to “Tom Courtenay,” and the latter hadn’t exactly convinced him he’d be able to pull off another ambitious conceit. “I wasn’t positive I had enough people I could round up who were ready to work on something for nothing, which all of those videos depended upon,” Morrison says. “But as Yo La Tengo pretty often do, they talked me into it.” He partnered with Upright Citizens Brigade writer Joe Ventura on a treatment, which he then took to L.A. to pitch to Bob and David. Luckily, despite their cult HBO series already entering its third season, Cross and Odenkirk were open to working for nothing, thanks to everyone already being pals—just as I’d always suspected.

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“There are so many mutual friends there that the degree of separation doesn’t really go beyond two people, in that music-comedy world,” Cross says. “It’s a lot of like-minded people with not wholly dissimilar talents and interests.” Much of that scene had coalesced around New York, where Morrison saw his first stand-up show (Jake Johannsen, if you’re curious) with comedy fans Kaplan and Hubley, then became involved with UCB and began hanging around the Luna Lounge, where he first met Cross. Meanwhile, Kaplan and Hubley had met Odenkirk while on vacation in Santa Monica, where he did a performance at a Borders bookstore.We loved him on Larry Sanders, and we were definitely interested in seeing Stevie Grant doing comedy,” Kaplan explains. “We’re not the most outgoing people, but this was so low-key that it seemed possible to approach him afterwards and introduce ourselves, and he expressed some awareness of the band.”

Odenkirk later brought Cross to see the group open for Big Star at New York’s Tramps, about which McNew recalls, “I was completely starstruck and in awe.” A Mr. Show premiere party followed later at L.A.’s El Rey Theatre, where Cross commissioned Superchunk to play while Odenkirk invited Yo La Tengo—as it happens, the same day the band was in town to record its version of The Simpsons theme. (“The line between fantasy and reality got completely obliterated that day. It was like a waking dream,” McNew recalls.) In short, by the time Morrison approached Cross and Odenkirk with “Sugarcube,” everyone was already nice and friendly. Almost too friendly.

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“I remember it made me concerned—but simultaneously alleviated my concern—how confidently casual Bob and David were about it,” Morrison says. “And I realized, oh yeah, they’re going to be able to just come in and make everything they do great automatically.”

Morrison was just left to worry about scrounging up resources, some of which he drew on from a serendipitous commercial gig. The production took place over two days at Santa Monica College, which Morrison, production designer Dave Doernberg, and set dresser Damon Chessé filled with posters and other rock memorabilia, much of it drawn from Chessé’s personal collection. Cross and Odenkirk’s wardrobe—a garish clash of silver lamé jumpsuits, KISS makeup, and BDSM wear—was picked up at random places along Hollywood Boulevard. And the rock school’s student body was a combination of working extras and random volunteers, including the poufy-haired Sammy Hagar look-alike who gets a spotlight moment lip-syncing the song’s chorus, and who just happened to be a former touring member of Poison.

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And again, there were friends, including members of the lo-fi pop band Refrigerator and Bill Ryan, owner of the legendary Hoboken, New Jersey record shop Pier Platters, and Morrison’s frequent muse, having previously appeared in his videos for Sonic Youth and Superchunk. Ryan—who plays “Billy,” the bouncer checking credentials outside the teachers’ lounge—was on tour with Beck at the time, and it was he who provided the “all-access laminate” Cross taunts Kaplan with. It’s a scene that Kaplan calls “my personal highlight of my acting. We did something like four takes, and one of them, [David] laughed before I did, and I thought I was making great strides as a performer.”

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As for where the rest of those riffs originated, time has all but erased their memory.

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“There’s a thing where we’re yelling at them, right?” Cross says. “I think there was a lot of yelling, and as I recall, those guys were doing a lot of breaking up as we were yelling at them, and they were having a lot of difficulty keeping their shit together. But that’s about it.”

Morrison himself is only sort of sure that both “The Foghat Principle” and “Closer To The Heart” originated with Odenkirk (“He wanted a lot of opportunities to have his glasses down there at the tip of his nose,” he says of the latter), though he adds, “I’m proud of ‘Burning Out vs. Fading Away.’ That was mine. That’s my handwriting on the chalkboard.” However, nearly everyone remembers that there was a version that ran nearly twice as long, with the song looped to make it fit. (“It was a little bit annoying,” Kaplan says.) In the extended cut, Morrison recalls deleted scenes featuring an emergency eye wash station for glitter and a sequence where they’re all assigned to make Thanksgiving hand-turkeys, because “we wanted it to also be school, not just rock.” Where that cut ended up, however, no one knows. And no one has seen—or even really thought about—the “Sugarcube” video at all since then.

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Which makes sense. After all, it was just a quick, two-day shoot, barely a blip in Bob’s and David’s rapidly accelerating careers. It wasn’t even the only Phil Morrison short about an indie-rock group being forced to act out rock ’n’ roll clichés that Cross would star in that year. He and Garofalo would also appear as pushy, pretentious directors in Superchunk’s “Watery Hands,” the spiritual twin to “Sugarcube.”

And of course, both would go on to become much, much more famous, with far bigger TV and movie gigs to their credit—and, in Odenkirk’s case, a starring role in a prestige drama that left him, unfortunately, too busy to talk about some 20-year-old music video with some emotionally stunted kid. Meanwhile, Ennis (whom McNew notes has “aged incredibly well into this ruggedly handsome, Sam Elliott-like movie star”) was initially enthusiastic about participating, but ultimately he couldn’t fit it into his schedule of filming a pilot for Ron Howard. In short, everyone has long since moved on from “Sugarcube.” If they remember it at all (Cross barely does), it’s as a fun afternoon, just another cool hang among longtime friends. What they don’t remember is any sense of it being a particularly epochal moment, one that I recall playing across MTV several times a day.

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“Is that true? I don’t think that’s true,” Kaplan says. McNew agrees: “Ira’s right. It might have been shown twice. Which doubled our playtime, which was amazing.”

All right, maybe I’m nostalgically inflating that, too. Nevertheless, surely even that relatively wide exposure—and the coolness conferred upon the group by its Mr. Show association—was noteworthy for the band? Surely it meant something?

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“When we were touring on that record, it was very different than any other tour we had been on—you know, kind of inescapably so. I’m sure the video contributed,” Kaplan modestly allows. And yet, despite its sort of success, “Sugarcube” would prove to be Yo La Tengo’s last video for the next 16 years, as MTV’s slow abandonment of the format and the rise of YouTube made music videos mostly redundant, particularly for an indie band without a lot of money to burn. Still, Morrison and the group say they occasionally entertained the idea of doing a “Sugarcube” sequel.

“I remember having some notion of a video for ‘Little Honda,’ in which we’re trying to get to an awards ceremony because we’d been nominated for our ‘Sugarcube’ video,” Kaplan says. Morrison adds, “For one record of theirs more recently, the notion came up of doing a sequel, if Bob and David were willing. It’d be about Yo La Tengo going back and visiting their old professors, who are not doing well and are old, and never, ever do anything to be funny. Unless someone thought that very fact was funny. That’s fine, that’s their business.”

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“I can’t remember which one I died in,” McNew says. “That might have been my treatment.”

Alas, none of these ideas ever came to fruition, leaving Cross and Odenkirk’s professors forever youngish and McNew alive, still so much rocking to do. In the meantime, Morrison went to work on the Upright Citizens Brigade TV show—at least partially, he says, because “Sugarcube” proved he had comedic chops—where he oversaw sketches like the classic “Ass Penny.” In 2005, he directed the Oscar-nominated film Junebug, and soon after he took charge of Apple’s “Get A Mac” campaign and Allstate’s “Mayhem” commercials—both of which have been seen by millions more people than “Sugarcube” ever was. He’s only done a handful of music videos since, including Yo La Tengo’s return to the form, 2013’s “I’ll Be Around” and Superchunk’s “Me & You & Jackie Mittoo,” coincidentally released the same year once again. Of “Sugarcube” itself, Morrison is proud that it exists, but he doesn’t see it as particularly culturally significant. “What it mostly did was contribute to me not wanting to do anything like it ever again, because I already did it,” he says.

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“I’m not aware of any legacy,” Cross agrees, barely concealing his confusion at why we’re even talking about this. He’s not alone. “Sugarcube” lives on solely in shitty YouTube rips, so blurry you can’t even make out what bands are on some of the posters. There is no call to preserve or canonize “Sugarcube.” Everyone involved is glad that people still like it; everyone was happy to be a part of it. But as a cross-cultural summit, some apotheosis of the indie-rock and alt-comedy nexus, a symbol of the rapidly accelerating convergence that would see L.A.’s Largo become a hotbed for comics swapping sets with musicians; Sub Pop releasing albums by Cross, Silverman, Oswalt, and Eugene Mirman; Tom Scharpling finding his record-geek comedy partner in Superchunk’s Jon Wurster; and indie-rocker-turned-comedian Fred Armisen pairing with Sleater-Kinney’s Carrie Brownstein on Portlandia? No one really sees “Sugarcube” as an important moment within that lineage. To them, it was just part of a natural evolution, an outgrowth of something “that’s been going on since really jazz musicians and ’60s comics,” Cross says.

“This is our youth, so you know, there’s this temptation to think you’re doing something that’s never been done before,” Kaplan says. “It just means you haven’t done it before.” As both Kaplan and McNew are quick to remind, comedians like Steve Martin and Albert Brooks cut their teeth opening for rock bands. To them, it’s not all that different than Todd Barry opening for Yo La Tengo at Maxwell’s.

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Still, no one was ever going to mistake Albert Brooks for a member of Sly And The Family Stone. (“He had very long hair back then. Don’t sell him short,” Kaplan counters.) But to return to Barry, he—like Wurster, like Armisen—is a drummer, and an ideal representative of just how seamlessly ’90s musicians and comedians were commingling, to the point where you couldn’t tell whether a guy approaching the stage was about to deliver a song or a dick joke.

“Quite often—not 100 percent of the time—the drummer is the funniest guy or lady in the band,” Cross explains. “So you see a lot of drummers threaded throughout the golden era of alt-comedy. You see a lot of drummers making appearances in things. Jon Wurster is a great example of that, as funny and talented as a comic voice as he is a drummer and encyclopedia of musical knowledge.” Kaplan adds, “You know, it’s the guy who’s in a band and he’s hilarious, so when the band thing doesn’t work out quite the way you maybe thought it would—or maybe never expected it to—there’s this other side of their personality that comes to the fore.”

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“I think it’s really comedians were the first people of indie-rock generation to become famous,” Morrison says. “Comedy seemed like real, official show business—even what was called ‘alt-comedy,’ because people who were in alt-comedy were also in big movies and stuff. Indie rock, that felt like it had a ceiling on it in terms of popularity. It felt self-selecting. So when the two things mix, I think back then there was still that feeling of, ‘Oh, wow! So-and-so even knows about this band?’ With Bob and David, it really felt like, wow, these famous people are willing to be in the Yo La Tengo video. That seemed really extraordinary.”

This is as close as anyone comes to validating my thesis that “Sugarcube” was more than just a funny video, but also somehow historically important (particularly to a kid with vaguely defined showbiz dreams of his own) in capturing the confluence of indie rock and comedy and the sensibilities that briefly defined a generation—as perfect a time capsule of the era as any.

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On the other hand: “Maybe we just liked talking to each other,” McNew shrugs. That sums it up pretty well, too.