In the Grammys' first year, 1958, Sinatra took home just one award -- for art direction. The legendary star, who had two No. 1 albums on the Billboard 200 that year, was not amused. No other recording artists were nominated for art direction for more than 30 years. But this has become more prevalent in the past 30 years, as artists exert more control over their album packages, and because the Recording Academy added a second category in the “package field” in 1995 for more elaborate packages.
At the upcoming 63rd annual Grammy Awards, McCartney is nominated for best boxed or special limited edition package for Flaming Pie (Collector’s Edition), a deluxe reissue of his 1997 album. He worked on the package with Linn Wic Andersen, Simon Earith and James Musgrave.
Tweedy is competing in the same category as one of two art directors on Wilco’s Ode to Joy. Tweedy is nominated alongside Lawrence Azerrad.
Hooper is nominated in a separate category, best recording package, for her work on Grouplove’s Healer. Her co-nominee is Julian Gross.
A previous McCartney reissue, Wings Over America (Deluxe Edition), won a 2013 Grammy for best boxed or special limited edition package, but McCartney didn’t personally win an award. The award went to the art directors, Earith and Musgrave (with whom he collaborated on the new package).
Here are all 14 recording artists who have won Grammys for art direction in either of these two categories in the package field.
Frank Sinatra, 1958. Ol’ Blue Eyes won his first Grammy as art director of his album, Frank Sinatra Sings for Only the Lonely. The album was also nominated for album of the year.
Suzanne Vega, 1990. The singer won her only Grammy to date as one of three art directors on her third studio album, Days of Open Hand. The others were Jeffrey Gold (then a top executive at A&M Records) and Len Peltier. The album was also nominated for best contemporary folk recording.
Joni Mitchell, 1995. The legendary artist and songwriter won two Grammys -- best pop album and best recording package -- for her 15th album, Turbulent Indigo. (She shared the latter award with her co-art director Robbie Cavolina.)
Frank Zappa, 1995. The brilliant innovator won for his work on his double album Civilization Phaze III, which was released posthumously in 1994. He worked on the art direction with his wife, Gail Zappa.
Ray Benson, 1999. The leader of Asleep at the Wheel won two Grammys -- best recording package and best country instrumental performance -- for the band's 21st album, Ride With Bob. He shared the recording package award with Sally Carns and Buddy Jackson. Ride With Bob was also nominated for best country album.
Ani DiFranco, 2003. The singer won her only Grammy to date for recording package for her 12th studio album, Evolve. She shared the award with her co-art director Brian Grunert.
Aimee Mann, 2005. The singer won her first Grammy for best recording package for her fifth studio album, The Forgotten Arm. She shared the award with her co-art director, Gail Marowitz.
Adam Jones, 2006. The Tool guitarist won his third career Grammy for best art direction for the band's fourth studio album, 10,000 Days. A track from the album, "Vicarious," was nominated for best hard rock performance.
Red Hot Chili Peppers, 2006. The band members won four Grammys for their ninth studio album, Stadium Arcadium. The haul also included best rock album and two awards for the smash “Dani California.” The double-disc album was also nominated for album of the year. The band members teamed with Matt Taylor on the art direction.
Neil Young, 2009. Young won his first Grammy in any category (!) as one of the art directors of The Archives Vol. 1 1963-1972. The box set encompassed 10 DVD/Blu-ray discs or eight CDs. His collaborators on the art direction were Gary Burden and Jenice Heo.
Jack White, 2010. White won for his work on The White Stripes’ Under Great White Northern Lights (Limited Edition Box Set). The box set includes the Under Great White Northern Lights documentary, the 16-track live album CD, and the same 16-track live album on 180-gram vinyl. White worked on the package with Rob Jones. White has won twice more in the category for The Rise & Fall of Paramount Records Volume One (1917-27) and Volume Two (1928-32).
Jeff Ament, 2014. The Pearl Jam bassist has won two of his three career Grammys for best recording package. He won for his work on Pearl Jam's 10th studio album, Lightning Bolt, and again five years later for his work on Chris Cornell's posthumous, eponymous album. He shared both awards with Joe Spix. He also shared the award for Lightning Bolt with Don Pendleton and Jerome Turner.
Father John Misty, 2017. The artist, aka Josh Tillman, won his only Grammy to date for best recording package for Pure Comedy, his third studio album. The album was also nominated for best alternative music album. Tillman shared the art award with Sasha Barr and Ed Steed. Tillman had been nominated for best boxed deluxe or special edition package two years previously for I Love You, Honeybear (Limited Edition Deluxe Vinyl).
“Weird” Al Yankovic, 2018. The parody master won his fifth career Grammy for Squeeze Box: The Complete Works of “Weird Al” Yankovic, a 15-album box set. Yankovic worked on the package with Meghan Foley and Annie Stoll.
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