West's Graduation is up for awards including Album of the Year and Rap Album of the Year, while his tracks "Can't Tell Me Nothing" and "Good Life" have both been nominated for Best Rap Song.
Winehouse's Back to Black is also up for the coveted Album of the Year gong, and her hit single "Rehab" is nominated for both Song of the Year and Record of the Year, going up against Rihanna's Umbrella, which is also recognized in the two categories.
Justin Timberlake and Foo Fighters, who both received a total of five nods apiece, are also in the running for Record of the Year with their respective releases "What Goes Around... Comes Around" and "The Patience."
Foo Fighters' Echoes, Silence, Patience & Grace will compete for Album of the Year and Best Rock Album.
Other multiple nominees, announced on Thursday morning, include Jay-Z, who has six nods including Best Rap Album for Kingdom Come, while Bruce Springsteen, Akon, Chris Daughtry and Ne-Yo have each received four nominations.
Elsewhere, Paul McCartney, Bon Jovi and Maroon 5 are all up for Best Pop Vocal Album; Tim McGraw, Brad Paisley and Vince Gill will fight it out for Best Country Album; and Keyshia Cole, Ne-Yo and Akon compete for Best Contemporary R&B Album.
The winners will be revealed at a ceremony in Los Angeles on Feb. 10.
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