The Grammys, as the Recording Academy likes to remind us, are “music’s biggest night.” They’re also an unparalleled opportunity for a varied group of artists across genres—from country to soul to rap—to convene under one roof for an evening. With so much distinctive talent in one place, it’s become a tradition for the show’s producers to dream up the most unexpected medleys and mashups.
Sometimes, these collaborations are a thrill to watch. Other times, they leave viewers scratching their heads. In preparation for Sunday night’s ceremony, here’s a roundup of 10 of the most memorable, from Eminem and Elton John’s seminal duet to that time Gwyneth Paltrow joined CeeLo Green onstage, accompanied by a gaggle of Muppets.
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Eminem and Elton John (2001)
The rapper from Detroit and the British music legend were paired up for a duet at 2001’s ceremony. The performance came in the wake of accusations leveled at Eminem over purportedly homophobic lyrics in The Marshall Mathers LP. At the time, GLAAD, which had previously honored John, was protesting the rapper. But their rendition of Dido’s “Thank You” ended up serving as the start of a meaningful friendship for the unlikely duo.
Moby, Jill Scott and Blue Man Group (2001)
2001 also provided an unusual opportunity for soul singer Jill Scott and electronic musician Moby to get backing on a performance of “Natural Blues” from performance artists Blue Man Group. While the combination makes sense in some ways—Scott’s voice is a natural fit for Moby’s remake of the original “Trouble So Hard” gospel song—the Blue Man Group’s zany appearance mostly just feels out of place.
The Black Eyed Peas, Gwen Stefani, Eve, Maroon 5, Los Lonely Boys and Franz Ferdinand, 2005
In a nearly 12-minute performance, everyone from Fergie and Gwen Stefani to Maroon 5 and Los Lonely Boys got together for this massive kickoff to the 2005 event. It began with “Let’s Get It Started,” appropriately enough, before cycling through “Rich Girls,” “How Far Is Heaven,” “This Love,” and “Take Me Out.” And while each of those songs were blockbusters in their own right, choppy transitions hampered the mega-mashup.
Gorillaz, Madonna, and De La Soul (2006)
In this 2006 segment, digital projections of the Gorillaz segued into the real-life appearance of hip-hop trio De La Soul, who then vacated the stage for a holographic version of Madonna to appear alongside the Gorillaz. The true Madonna eventually steps out—in a shiny leotard and little else—to strut her stuff to the disco strains of “Hung Up.” While the Gorillaz track has a low-key vibe, Madonna’s danceable song kicked things up several notches. The performances delivered individually, but they never quite coalesced into a cohesive statement.
Linkin Park, Jay Z and Paul McCartney (2006)
Alt-rock meets hip-hop meets a legend of classic rock in this true hodgepodge of musical styles. The mix of Linkin Park’s “Numb” and Jay-Z’s “Encore” actually makes for a surprisingly seamless mashup, before Sir Paul joins the fun with a rendition of “Yesterday” to end on a nostalgic note. While this may seem like a strange trio at first glance, ultimately, it worked.
CeeLo Green, Gwyneth Paltrow and the Muppets (2011)
CeeLo Green’s peppily profane “F—k You” got a PG makeover with this Muppets-accompanied performance, during which the singer topped even his own outlandish fashion sense with a colorful feathered getup and bejeweled cap. To add to the confusion, Gwyneth Paltrow—yes, that Gwyneth Paltrow—stepped in for a guest verse. (She was promoting the country music movie Country Strong at the time, which explains the detour into music.)
David Guetta, Chris Brown, Lil Wayne, Foo Fighters and deadmau5 (2012)
The ceremony in 2012 brought with it another giant medley, this time an eight-minute blend of dance music, rap, R&B and rock. With David Guetta DJing for the crowd, Chris Brown and Lil Wayne took their best shot at maintaining control over a club beat. Things then switched over to the Foo Fighters, who had won five Grammys that evening, for a major tonal change—before deadmau5 took the reins and dropped the beat. It feels a bit like musical whiplash, but then again, 2012 was a weird time for music.
Metallica and Lang Lang (2014)
In this unexpected mix of soft and hard, the celebrated concert pianist Lang Lang starts off with a solo, but the collaboration quickly gives way to Metallica’s heavy metal sounds. Lang Lang continues to infuse the performance with some delicate piano riffs, although the result feels discordant at times as he’s forced to compete with Metallica’s aggressive guitar reverb.
Kendrick Lamar and Imagine Dragons (2014)
An anthemic radio rock band and one of the year’s most provocative rappers? Sure, why not. The back-and-forth between Imagine Dragons’s melodic stylings and Lamar’s fiery rhymes feels jarring at first. But all parties fully commit to the duet, and in the end, it makes for one of the more intriguing collaborations to come out of the Grammys. As they play off each other’s high energy, Lamar especially finds a hypnotic groove.
