Joe Cocker & Jennifer Warnes, "Up Where We Belong," 1982. The gravel-voiced rock veteran teamed with the crystalline-voiced pop singer on this Oscar-winning song from the movie An Officer and a Gentleman. This won for best pop performance by a duo or group with vocal. It was Warnes' first Grammy and Cocker's only one.
Al Green & Lyle Lovett, "Funny How Time Slips Away," 1994. The track, drawn from the multi-artist concept album Rhythm, Country and Blues, won for best pop vocal collaboration. This was Green's ninth Grammy and his first outside the soul gospel categories; it was Lovett's second Grammy and his only one to date outside the country categories.
Elvis Costello & Burt Bacharach, "I Still Have That Other Girl," 1998. These men of different generations and musical sensibilities joined forces on the collabo album Painted From Memory. This brooding ballad won for best pop collaboration with vocals. This was Bacharach's fifth Grammy and Costello's only one to date.
Santana feat. Everlast, "Put Your Lights On," 1999. The classic Latin/rock band teamed with a former member of the hip-hop group House of Pain for this track. This was one of three Grammy-winning collabos from Santana's 18th studio album, Supernatural. The song won for best rock performance by a duo or group with vocal. This is Everlast's only Grammy to date.
Eve feat. Gwen Stefani, "Let Me Blow Ya Mind," 2001. The rapper and the pop star (then still fronting No Doubt) teamed for this track from Eve's sophomore album, Scorpion. This was the first winner in the Grammys' new best rap/sung collaboration category. This was Stefani's first Grammy and Eve's only one to date.
Sting & Mary J. Blige, "Whenever I Say Your Name," 2003. The cool Englishman teamed with the queen of hip-hop soul on this track from his seventh solo studio album, Sacred Love. This won best pop collaboration with vocals. It was Sting's 16th Grammy and Blige's third (and her only one to date in the pop field).
Loretta Lynn feat. Jack White, "Portland, Oregon," 2004. The country queen teamed with the leader of The White Stripes on this track from her 42nd solo studio album, Van Lear Rose. This track showcases both his alternative nature and her country roots. This won for best country collaboration with vocals. White produced the album, which won best country album.
Gorillaz feat. De La Soul, "Feel Good Inc.," 2005. The British virtual band and the veteran alternative hip-hop trio came together on this smash from Gorillaz's sophomore album, Demon Days. In addition to winning for best pop collaboration with vocals, this was nominated for record of the year. This is the only Grammy to date for both artists.
Linkin Park/Jay-Z, "Numb/Encore," 2005. This mash-up, which won for best rap/sung collaboration, combines tracks from two vastly different 2003 albums. "Numb" was the closing track on Linkin Park's Meteora. "Encore" was from Jay-Z's Grammy-nominated The Black Album. This was the highlight of their collaborative EP Collision Course.
The Chemical Brothers feat. Q-Tip, "Galvanize," 2005. The electronic music duo teamed with the rapper on this track from their fifth studio album, Push the Button. It won best dance recording. The Chemical Brothers also won for best electronic/dance album. This is Q-Tip's only Grammy to date.
Bon Jovi with Jennifer Nettles, "Who Says You Can't Go Home," 2006. The rock band teamed with the country singer, moonlighting from Sugarland, on this hit from their ninth studio album, Have a Nice Day. This reached No. 1 on Hot Country Songs and won best country collaboration with vocals. It was Nettles' first Grammy and Bon Jovi's only one to date.
Robert Plant & Alison Krauss, "Please Read the Letter," 2008. The former lead singer of Led Zeppelin teamed with the bluegrass and country star on the album Raising Sand. Three tracks from the album won Grammys in pop and country performance categories. This one took record of the year. Before their collaboration, Plant had won just one Grammy; Krauss had won 20.
Tony Bennett & Lady Gaga, Cheek to Cheek, 2014. When, at the 2009 awards, Gaga won best dance/electronic album for The Fame and Bennett was nominated for best traditional pop vocal album for A Swingin' Christmas, did anybody seriously think that these two artists would one day team up for a Grammy-winning album? It happened just five years later when this won best traditional pop vocal album.
Taylor Swift feat. Kendrick Lamar, "Bad Blood," 2015. The pop megastar teamed with the most acclaimed rapper of his time for this retooled version of a song from her fifth studio album, 1989. It won for best music video and it was one of three Grammys Swift won that year and one of five for Lamar. Lamar won in the same category two years later on his own with "Humble."
Pentatonix feat. Dolly Parton, "Jolene," 2016. The pop vocal group teamed with the country icon for this acapella remake of her 1973 classic. This won best country duo/group performance. The track, from Pentatonix's EP PTX, Vol. IV—Classics, brought the quintet its only Grammy to date in a performance category. Their other two are for arrangements.