Ervin Drake’s “It Was A Very Good Year,” was originally recorded by Bob Shane of The Kingston Trio in 1961, but it was Frank Sinatra’s rendition in 1965 that made the song legendary with his GRAMMY Award winning version in D-minor. 

Sinatra’s version of the song, which won Best Vocal Performance, Male, also took home the GRAMMY for Best Instrumental Arrangement Accompanying Vocalist by Gordon Jenkins. The song became Sinatra’s first number one single on The Adult Contemporary chart and reached number 28 on The Billboard Hot 100. “It Was A Very Good Year” appeared on Sinatra’s 1965 album September Of My Years and again on his Sinatra At The Sands live album in 1966. 

“It Was A Very Good Year” has been recorded by many artists such as Don McLean, Richie Havens, Herb Alpert & The Tijuana Brass, Lou Rawls, Eartha Kitt, The Flaming Lips, Robbie Williams and Ray Charles as a duet with Willie Nelson.  Most recently, in 2011, Dee Snider of Twisted Sister recorded a version of the song for the album SIN-atra, a heavy metal cover album of Frank Sinatra songs.  “It Was A Very Good Year” also appeared on the 78th episode of The Muppet Show, was featured in the 1991 Spike Lee film Jungle Fever and was used as the opening song in the second season premiere of HBO’s The Sopranos.

All bios appear as they were submitted in the year of induction or award presentation.