It’s Weird ’90s Week on Stereogum. All week long we’re looking at the strangest musical moments and trends of the decade. Check out more here.

In the 1990s it often felt like television shows were trying to out-hip each other to get a piece of that Alternative Nation demographic, often not exactly knowing what in the hell they were doing. Remember when Cibo Matto appeared on Buffy The Vampire Slayer? Or when Luscious Jackson were on Clueless? Or when Cypress Hill stole the London Philharmonic Orchestra from Peter Frampton on The Simpsons? Or when Friends embarrassingly revolved an entire episode around Hootie And The Blowfish?

It often looked like a total crapshoot, and when it worked, it was glorious. When it flopped, it was ugly. In celebration of a decade weird enough to have Anthrax appear on Married…With Children and Bob Dylan perform on Dharma And Greg, here are 10 of the most incredible, inexplicable, surreal, and wonderful moments when mainstream television did whatever it could to win over the Gen-X demographic in the 1990s.

Dinosaur Jr., The Jenny Jones Show (1997)

J Mascis and crew playing an ear-shattering rendition of “Out There” on a daytime talk show in front of a truly confused audience clapping on the one and three beats: If you’re looking for a perfect example of the gap between generations and musical tastes 20 years ago, this is it. To the band’s credit, they don’t hold back one iota (look at that rig) and pull off one hell of a blistering performance. Those poor mothers in the crowd probably didn’t know what hit them.

The Flaming Lips, Beverly Hills 90210 (1995)

One of the strangest moments of the era was in 1995, when Beverly Hills 90210 featured a cameo by the Flaming Lips, who were blowing up with their surprise hit “She Don’t Use Jelly.” In a perfect example of this confusing generational shift, the Lips’ performance was followed by a line that so desperately tried to sound cool, but failed hilariously: “You know, I’ve never been a big fan of alternative music, but these guys rocked the house.”

The Frogs With Sebastian Bach, Oddville (1997)

A favorite of Billy Corgan’s, Milwaukee band the Frogs enjoyed a bizarre, brief spell of notoriety, opening for the likes of the Pumpkins and Pearl Jam and becoming the most talked-about second-stage band at Lollapalooza 1994. After guitarist Jimmy Flemion joined Sebastian Bach’s touring band in 1997, Bach returned the favor the same year by appearing with the Frogs on the MTV show Oddville. The result is utter chaos as Baz and band roar through a rendition of fan favorite “Lord Grunge” that ends with the band trashing the set and Bach leaping on to a clearly flustered Rich Brown.

KISS, The Arsenio Hall Show (1993)

One of the best things about The Arsenio Hall Show was that it could always be relied upon for great musical performances. The show’s exposure of African-American talent was unparalleled, yet at the same time it welcomed a wide variety musical styles, with artists performing on a big, glitzy set. As a result, aside from Bill Clinton playing saxophone, not a lot of “weird” musical moments happened on the show. However, KISS’ appearance in 1993 is a curious little nugget, a snapshot of a band in desperate search of an identity, not to mention relevance. By then KISS were a decade into their “unmasked” era, their record sales were flagging, and every gimmick would be tossed out over the next two years: a live album, a tribute album, an Unplugged, and eventually the one gimmick that clicked: a full-blown original lineup reunion in 1996. On Arsenio, though, it was a serviceable but rather pointless hair metal run-through of “Detroit Rock City” by a band that looks like it doesn’t know what to do next.

The Lemonheads, Live With Regis And Kathy Lee (1992)

Riding the popularity of their cover of Simon And Garfunkel’s “Mrs. Robinson,” the Lemonheads quickly became indie rock darlings, with leader Evan Dando the scene’s poster boy. Appearing on a morning talk show has to be difficult for any touring musician, let alone something as popular as Regis And Kathy Lee in 1992, but Dando’s appearance on the program, while plenty surreal, is oddly sweet. He handles Regis’ shtick and Kathy Lee’s obnoxiousness with grace and humor, he says hi to his mom in the studio audience, and best of all, he turns in a sweet acoustic cover of “It’s A Shame About Ray.” Dando could have easily played the “apathetic slacker” thing on this most middle-of-the-road talk show, but he’s a total pro, and makes a very good impression.

Pavement, The Tonight Show With Jay Leno (1994)

As Pavement rode the wave of critical acclaim for the classic 1994 album Crooked Rain, Crooked Rain, they found themselves with a minor hit on their hands in the form of “Cut Your Hair.” In turn, that led to one of the most surreal musical moments of the decade, in which the indie faves were booked to appear on the straight-and-narrow The Tonight Show With Jay Leno. The guys played the “slacker” shtick with typical insolence and detachment, much to their detriment as it’s a generally shambolic performance, but Bob Nastanovich at least deserves credit for playing tambourine with as much passion as Will Ferrell on the cowbell.

Primus, The Dennis Miller Show (1992)

Who knows if the producers of The Dennis Miller Show knew what they were getting when they booked Primus to appear in 1992, but then again, Primus remain one of the most baffling (and endearing) success stories of the early 1990s. Something about their fusion of progressive rock, heavy metal, and funk clicked with the kids, and it is a joy to see the band tear through “Jerry Was A Racecar Driver,” Rush’s “YYZ,” and the MTV hit “Tommy The Cat.” The fact that a band as nerdy as Primus could be popular enough to appear on a late-night talk show is a wonderful example of how fun the ’90s were.

R.E.M., Sesame Street (1999)

The lure of nostalgia is irresistible whenever any generation approaches middle age, and by 1999 those who had grown up with Sesame Street in the 1970s were having kids of their own. So what better band to make an appearance than R.E.M., who had soundtracked those parents’ teen years in the 1980s? The band’s dislike of their hyper-ebullient “Shiny Happy People” was renowned, but to see them parody that song in the form of “Furry Happy Monsters” was adorable, and showed what good sports they were.

Stryper, Into The Night With Rick Dees (1990)

By 1990 Christian rockers Stryper were fully aware that their brand of evangelical pop metal had a very short shelf life with mainstream audiences, so in 1990 they released the album Against The Law in an attempt to stay somewhat relevant. Gone were the yellow-and-black spandex outfits and preachy lyrics, replaced by a much more secular-leaning aesthetic. Needless to say, it flopped, but they still wound up appearing on Into The Night With Rick Dees to perform their sleazed-up, weirdly asexual cover of Earth Wind & Fire’s classic “Shining Star.”

Ween, The Jane Pratt Show (1993)

Give Jane Pratt a ton of credit; it was a daring move to book lo-fi geniuses Ween on her Lifetime talk show in 1993, but the Sassy (and ultimately xoJane) founder holds her own interviewing Gene and Dean, and the boys turn in a stunning lo-fi performance of “Freedom Of ’76,” which was still a year away from appearing on record. As Deaner went on to say about this clip, “This was filmed early in the morning and we were very stoned.” Either way, this is pure magic, and hopefully a few Lifetime viewers were made Ween fans. With a song like this, who could resist?