Neil Diamond and Barbra Streisand (1980)

Bill Simmons: Here are four minutes that will make you ask yourself things like, “Why am I enjoying this so much?” … “Are these two just going to start humping on the stage?” … “Is there any definitive way to figure out who had a worse hairdo?” … “If these two had reproduced, would they have given birth to Moses?” … “Am I paying enough attention to my wife? Should I make sure she doesn’t identify with these lyrics a little too much?” … “Could an NBA team wear Streisand’s outfit as warm-ups for a game?” … “Is it wrong that I keep getting the chills during this performance?” … “Was this the greatest Emmys moment of all time?” … “Was this the greatest Jewish musical moment of all time?” … “Was this the greatest Jewish moment of all time?” … “Was this the greatest duet of all time?” … “Did this inadvertently lead to hundreds of horrendous duets to come?” … “Why is this so fucking riveting?” … and most importantly, “Did any female singer ever have a better voice than Barbra Streisand?”

Bob Dylan (1980)

Alex Pappademas: General rule: It’s super corny to act like you’re too hip to be at the Grammys if you’re, y’know, at the Grammys. This applies to everyone except Bob Dylan. Playing squirrelly straight man to Stevie Wonder, paraphrased from a 19th-century German rabbi) out of his hat, sending a sinister riverboat gambler to perform on his behalf, or fell victim to a cryptic act of protest in 1998 — dude was soy-bombing these shows before soy-bombing was cool.

This 1980 take on “Gotta Serve Somebody” — Dylan’s first appearance on the show as a performer — is something else. The song is from 1979’s Slow Train Coming, Dylan’s first Christian album. It won Best Rock Vocal Performance — Male that year, beating out the storied likes of “Is She Really Going Out With Him” and “Bad Case of Loving You,” which is weird because on record, “Gotta Serve Somebody” is glib and sterile and full of groaners, rhyme-wise: “You might be a construction worker, working on a home / You might be living in a mansion, you might live in a dome.” (Theory: Dylan’s discovery of rhyming dictionaries in the mid-‘70s derailed his art way worse than motorcycle accidents or God.) Here, though, Dylan shows up in black tie and bears down on the song like he’s banging nails into stone. On the album it’s an admonishment; this version is a threat. Like he said a month later, during an impromptu onstage sermon at a show in Canada: “When Jesus says love thy enemy as thyself, he doesn’t mean roll over and play dead.”

Linkin Park with Jay-Z and Paul McCartney (2006)

Bill Barnwell: It’s amazing that we got the nadir of two of the most legendary performers of the past 50 years at the same moment and the same time, but that’s exactly what happened here. It’s not even really the performance, but instead the moment where the person who uploaded this video to YouTube actually decided that Linkin Park needed to be the top-billed performer in the title bar and wrote that the song merely featured Jay-Z and Paul McCartney. Wait. This is supposed to be our favorite Grammy performances? Can it be our skin-crawlingest Grammy performances? What about that time Elliott Smith played “Miss Misery”? Oh, that was the Oscars? Shit.

Michael Jackson (1988)

Megan Creydt: Seriously, can you imagine being in the audience for this?

Jamie Foxx with T-Pain and Slash (2010)

Mark Lisanti: Some YouTubers have declared this the “worst Grammys performance ever.” This is almost hilariously incorrect. If for no other reason than Jamie Foxx emerged in a cape, then owned the stage like the pimpest Civil War general ever to write off the razing of a Southern city to moonshine overindulgence, this cannot be the worst. This must be among the best. Like anyone with ears, I can do without T-Pain’s cyborg caterwauling, but hey, there’s Doug E. Fresh! And then Slash shows up and rips through a bizarrely out-of-key version of the “November Rain” solo! This is among the greatest things I’ve ever seen, as a fan of being very confused by my own choices. (I also love this stupid, stupid song. I have no idea who I am.)

Usher and James Brown (2005)

Tess Lynch: I will not watch the Grammys unless I am guaranteed splits smothered in back flips layered with trampolines and garnished with James Brown. Anything else is disgusting and unless these standards are met, the kitten gets it.

Ol’ Dirty Bastard Crashes the Stage (1998)

Amos Barshad: “Wu-Tang is for the children.” You can quibble with the method of delivery here — ODB crashing the stage while Shawn Colvin and John Leventhal collect their Song of the Year award for “Sunny Came Home” — but you can’t argue the sentiment. Dirt was pissed that Puff Daddy and the Family’s No Way Out had beaten out Wu-Tang Forever for Best Rap Album earlier in the night and needed to make it known: “Wu-Tang is for the children.” And from the implicitly educational street stories of “Can It Be All So Simple” or “Little Ghetto Boys,” to the raw inspirational oomph of “A Better Tomorrow” or “It’s Yourz,” he’s always been right on that — “Wu-Tang is for the children.”

Color Me Badd and Boyz II Men (1992)

Dan Silver: Let’s start by pointing out that the person who uploaded this video not only had a VHS tape of the 1992 Grammy Awards, but he/she watched it (or this section) so many times the degeneration of his/her most rewatched or paused moments can actually be seen on screen (that’s what all the static and vertical hold issues are … I think I just revealed myself as a former video store clerk). But enough about my cousin Walter.

No matter what I say about this clip, I’ll only be sitting here thinking, “What would my buddy Rembert say?” (Dude, call me, I must know.) Plus, the awesomeness contained in this mind-numbing barrage of early-’90s tropes practically speaks for itself. So I’m just going to point you to some highlights:

• Comic Relief-shape Whoopi Goldberg referring to Color Me Badd and Boyz II Men as “very fine” (:04)
• The odd separation of the two groups. They’re on opposite sides of the stage on two different podiums. Why? (:28)
• Color Me Badd wardrobe highlights: frosted tips, dreadlocks, porn producer vests, and baggy leather pants (:29)
• Sexxxxxy Spanish talk (:58)
• Hype Man!!! (1:47)
• Boyz II Men wardrobe highlights: Cosby sweaters, fades, sunglasses indoors, sans pimp cane (1:48)
• ”It’s called rap. And we’re proud to be a part of it on the Grammy Awards.” The reveal that these two groups are presenting the award for Best Rap Performance by a Duo or Group, and consider themselves to be part of the rap community. OK, really? (3:13)
• Each nomination putting these two groups to shame (starting at 3:24), Public Enemy, Salt-N-Pepa, Heavy D, Naughty by Nature, DJ Jazzy Jeff and the Fresh Prince (OK … maybe not this one).
• DJ Jazzy Jeff and the Fresh Prince winning, and Will Smith not being in attendance (4:25)

Ah, the early ’90s.

Pearl Jam’s Speech (1996)

Michael Weinreb: Here are several upright gentlemen from a well-known grunge outfit accepting an award from Phoebe Buffay and some dude with a pompadour who once simulated intercourse with a topless model on a beach. I don’t know what this means. I don’t think it means anything. Except that Jeff Ament is the Amish Clyde Frazier.

Radiohead (2009)

Jonah Keri: Being an unapologetic USC fan these days is as tough as being a Radiohead fan is easy. I got my first live taste of both while living in L.A., the Trojans starting in the Paul Hackett Era of Doom and ending in the Palmer/Leinart/Bush glory years, Radiohead at a killer Hollywood Bowl show in 2003 (they even played “Creep,” which despite being their 114th-best song was a pretty cool surprise for noobs and vets alike). Thom Yorke’s crew and the Trojan Marching Band finally got together in ’09, and a great rendition of “15 Step” was the result. Too bad SC band members didn’t dress up like weird Sparty clones again the way they did when backing Outkast in ’04.