Steve Granitz/Getty Images/Michael Loccisano/Getty Images for NARAS/Jordan Strauss/Invision/AP/ There have been 61 Best Album of the Year winners since the first Grammys ceremony in 1959. Frank Sinatra and Stevie Wonder are tied for the most Best Album of the Year wins with three each. 2017 winner Adele has won twice, as has Taylor Swift, Paul Simon, and U2. Scroll down to see the album awarded the coveted Grammy from every year. Visit Insider's homepage for more stories. 1959: Henry Mancini — 'The Music from Peter Gunn' Harold P.