20 Weird and Wild Grammy Collaborations

The 2004 album Collision Course commemorated the coming together of rap-rockers Linkin Park and rock-interested rapper Jay Z – both near the height of their powers – as well as the solidification of "mash-up culture" in the music-business firmament. A little over a year after that album came out, the Grammys decided to get in on the action, too; the 2006 ceremony featured cross-genre pairings from all over the map. The biggest pairing, torch-passing wise, was definitely Paul McCartney's blessing of the Jay/LP track "Numb/Encore" with a few lines from the Beatles' much-beloved "Yesterday."

A lengthy tribute to the funk icon. Joss Stone, John Legend and Van Hunt's "Family Affair" started it off with some sparks; Fantasia's duet with Devon Lima (formerly of Abercrombie & Fitch-loving boy band LFO) got slightly manic before ending abruptly; Adam Levine of Maroon 5 supplied a straightforward nod to his band's blue-eyed soul roots, counterbalanced by Ciara's shaky vocal on "Everyday People"; will.i.am took the title of "Dance to the Music" literally with a performance that was more memorable for his footwork than for his freestyle, in which he called himself the "black Fred Astaire"; and Steven Tyler of Aerosmith scatted over the riffs of his usual foil Joe Perry, paired with Robert Randolph's slide guitar. Then – making good on one of the most rumored Grammy performances of the 2000s – Sly himself came out, sporting a huge blonde Mohawk and letting his acolytes take most of the mic duties during a boisterous, if somewhat anticlimactic, performance of "I Want To Take You Higher." The weird chaos definitely seemed analogous to Stone's twisted, lengthy travels along stardom's bumpy road.

Pop vocalist Keely Smith performed at the very first Grammy Awards show, back when it aired as part of the NBC Sunday Showcase in 1959. That year, she and Louis Prima won the inaugural Grammy for Best Performance by a Vocal Group or Chorus for their recording of "That Old Black Magic." To celebrate the 50th anniversary of the awards in 2008, Smith returned, then a spry and lively 75 years old, but Prima couldn't make it, on account of being dead for 30 years. Of the many non-Louis-Prima living male singers available (David Lee Roth would've killed it), somebody decided on Kid Rock, who occasionally sounds like he knows what he's doing. Also, that's Dave Koz hamming around beside them on saxophone.

In retrospect, this might not seem like that odd a team-up, now that Nick is grooving his way to solo fame with steamy R&B-flavored hits and Joe has assembled his own funk-pop band, DNCE. But at the time, the Jonases were just cute teenyboppers sharing the stage with a bona fide legend. Game as ever for whatever the Grammys asked of him, Stevie sounded right at home on the Jonases' "Burnin' Up," electronically modulating his voice for the intro. But the brothers weren't quite ready for Stevie's "Superstition." After the first verse, Nick cockily asks "Mind if I take this, Stevie?" "Come on, Nick," the elder graciously replies. And then the poor kid flubs the lyrics. Talk about bad luck.

A consummate professional, Frank Sinatra wasn't going to let a little thing like being dead for ten years keep him from opening the Grammys' 50th Anniversary show. After a clip (from the 1963 show) of Ol' Blue Eyes explaining how you win a Grammy (it's "not for selling a million records mind you — you get bread for that — this is for contributions to the art of recording"), Alicia Keys took the stage to play piano, dueting with a video image of the Chairman, though her ad libs ("Sing it, Frank") showed her trying a little too hard to generate chemistry.

Not since Fleetwood Mac's Tusk had rockers used a college marching band so effectively – in fact, Radiohead hired the same band that Lindsey Buckingham did. (Not the same band members of course, unless there was some 40-something tuba player who was really in no hurry to graduate.) But all those musicians don't upstage Thom Yorke, who was in fine, magnetically spidery form, leather-jacketed and shaggy-haired and looking like a genetically modified David Spade. Although this was Radiohead's first Grammy performance, it wasn't the Trojans' – they'd backed OutKast during the 2004 Grammys. And two weeks later they'd be back on TV, performing onstage at the Oscars with Beyoncé and Hugh Jackman.

How to deliver middle America "Fuck You," CeeLo Green's gleefully profane lament about a money-minded ex? The Grammys telecast brought the censored version, the Muppets and Gwyneth Paltrow (whose Nashville melodrama Country Strong had its wide release shortly before the ceremony). While Green wasn't backed by the Muppet house band, the Electric Mayhem, the combined visual spectacle of his outlandish getup, his felted backing singers (including one shocked pug), and Paltrow lustily belting out a verse made up for the lack of Animal. 

Aretha Franklin was in ill health in 2011 and the Grammys' version of a get-well bouquet was a show-opening performance of her biggest hits featuring ladies from pop, R&B, country, rock and gospel. The medley felt a bit disjointed – and certain singers' ill-fitting vocal stylings made Franklin's absence from the stage even more deeply felt – but it was, at least in length, a testament to the massive back catalog of the Grammys' most-decorated female pop icon. And one person felt like a little more time could have been carved out of the broadcast – season 3 American Idol winner Fantasia Barrino, who sat out the Grammys because of what she felt was a snub. "At the end of the day, I should have been on that stage," she told The Hollywood Reporter.

Though the 2012 Grammys' celebration of EDM might have seemed a little forced, the Recording Academy didn't broker this strange collaboration: Rat-headed festival DJ Deadmau5 had already remixed the Foos' "Rope" the previous year. As mouse-eared ravers look blissfully on, a straightforward rock performance gradually gives way to buzzsaw electronics and zero-gravity bass drops. After displaying his broad musical tastes, however, Grohl drew some flak for his acceptance speech that night, where he celebrated "the human element of music," saying, "Singing into a microphone and learning to play an instrument and learning to do your craft, that's the most important thing for people to do … it's not about what goes on in a computer."

Metallica have always prized the virtuoso chops, complex compositions, instrumental force and high seriousness of classical music. So this collaboration with the most renowned Chinese concert pianist of his age made some sense – at least in theory. Lang Lang performed a dramatic solo prelude as flames shot up behind him, and then the ominous guitar introduction to "One" upstages him and his playing slips into the ensemble. When he competes with the guitars during the song's solo sections, he can't match their volume and his playing grows harsh and discordant to compensate – certainly a more avant-garde moment than the Grammys usually offer. Lang would be back the following year in a more conventional setting, performing "Happy" with Pharrell and Hans Zimmer.

"I need y'all to recognize that Plan B is to win your hearts right here while we at the Grammys," Kendrick Lamar rapped during this mash-up of his brash good kid, m.A.A.d. city track with Imagine Dragons' stomping "Radioactive." While the lyric was a success-saluting variation on a verse he dropped at the end of 2013, the way he commanded the stage not only got Taylor Swift and Steven Tyler dancing, it turned the line into an instantly fulfilled prophecy.