Paul Simon, Frank Sinatra, Stevie Wonder and Taylor Swift are the only four artists to win Album of the Year three times. If Taylor wins today, she will own the record all to herself.
Frank Sinatra was the first artist to win the award in back to back years in 1966 and 1967 beating The Beatles both years. Stevie Wonder won the award three years out of four and Swift is the only female to win three times.
Sinatra won for ‘Come Dance With Me’ in 1960 beat Harry Belafonte ‘Belafonte at Carnegie Hall’, Henry Mancini ‘More Music From Peter Gunn’, Van Cliburn ‘Rachmanioff Piano Concerto No 3’ and Robert Russell Bennett ‘Victory at Sea Vol 1’.
‘September of My Years’ won in 1966 beating ‘Help! By The Beatles, ‘My Name Is Barbra’ by Barbra Streisand, ‘My World’ by Eddy Arnold’ and ‘The Sound of Music’ soundtrack.
In 1967 he won for ‘A Man and His Music’ beating ‘Color Me Barbara’ by Barbra Streisand, ‘Doctor Zhivago’ soundtrack, ‘Revolver’ by The Beatles and ‘What Now My Love’ by Herb Alpert.
Stevie Wonder ‘Innervisions’ won in 1974 beating Charlie Rich ‘Behind Closed Doors’, Bette Midler ‘The Divine Miss M’, Robert Flack ‘Killing Me Softly With His Song’ and Paul Simon ‘There Goes Rhymin’ Simon’.
Stevie won again in 1975 for ‘Fullfillingness’ First Finale’ beating Paul McCartney ‘Band On the Run’, John Denver ‘Back Home Again’, Elton John ‘Caribou’ and Joni Mitchell ‘Court and Spark’.
In 1977 Stevie Wonder won again for ‘Songs In The Key of Life’ beating George Benson ‘Breezin’, ‘Chicago ‘Chicago X’, Peter Frampton ‘Frampton Comes Alive’ and Boz Scaggs ‘Silk Degrees’.
In 1976 Paul Simon ‘Still Crazy After All These Years’ won beat Janis Ian ‘Between The Lines’, Elton John ‘Captain Fantastic and the Dirt Brown Cowboy’, Linda Ronstadt ‘Heart Like a Wheel’ and Eagles ‘One of These Nights’.
In 1987 Paul won again for ‘Graceland’ beating Peter Gabriel ‘So’, ‘Janet Jackson ‘Control’, Barbra Streisand ‘The Broadway Album’ and Steve Winwood ‘Back in the High Life’.
Simon’s other time was actually a win for Simon & Garfunkel so technically he has really won twice, but for the sake of the argument ‘Bridge Over Trouble Water’ won in 1971 beating ‘Chicago’ by Chicago, ‘Close To You’ by The Carpenters, ‘Déjà vu’ by Crosby, Stills, Nash & Young, Elton John ‘Elton John and ‘Sweet Baby James’ by James Taylor.
Swift won for ‘Fearless’ in 2010 beating Dave Matthews Band ‘Big Whiskey & the GrooGrix King’, Black Eyed Peas ‘The E.N.D.’, Lady Gaga ‘The Fame’ and Beyonce ‘I Am … Sasha Fierce’.
In 2016 she won again for ‘1989’ beating ‘The Weeknd ‘Beauty Behind the Madness’, Alabama Shakes ‘Sound & Color’, Kendrik Lamar ‘To Pimp a Butterfly’ and Chris Stapleton ‘Traveller’.
In 2021, Taylor Swift ‘Folklore’ won beating ‘Black Pumas’ by Black Pumas, Jhene Aiko ‘Chiombo’, Jacob Collier ‘Djesse Vol 3’, Coldplay ‘Everyday Life’, Dua Lipa ‘Future Nostalgia’, Post Malone ‘Hollywood’s Bleeding’ and Haim ‘Women in Music Pt. III’.
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