"It Was a Very Good Year" is a song Ervin Drake composed in 1961 for and originally recorded by Bob Shane with The Kingston Trio. It was subsequently made famous by Frank Sinatra's version in D minor, which won the Grammy Award for Best Vocal Performance, Male in 1966. Gordon Jenkins was awarded Grammy Award for Best Instrumental Arrangement Accompanying Vocalist(s) for the Sinatra version. This single peaked at #28 on the U.S. pop chart and became Sinatra's first #1 single on the Easy Listening charts. That version can be found on Sinatra's 1965 album September of My Years, and was featured in The Sopranos season two opener, "Guy Walks into a Psychiatrist's Office...". A live, stripped-down performance is included on his Sinatra at the Sands album.
The song recounts the type of girls the singer had relationships with at various years in his life: when he was 17, "small-town girls on the village green"; at 21, "city girls who lived up the stair"; at 35, "blue-blooded girls of independent means". Each of these years he calls "very good". In the song's final verse, the singer reflects that he is older, and he thinks back on his entire life "as vintage wine". All of these romances were sweet to him, like a wine from a very good (i.e., vintage) year.
Ervin Drake's inspiration to write the song was his then wife-to-be, Edith Vincent Bermaine. She was a showgirl, whom he had dated, and eventually married twenty years after the song was written.
The Kingston Trio introduced the song on their album Goin' Places (1961). This is the recording that influenced Frank Sinatra to want to record his own version.
Lonnie Donegan released it as a 45 rpm single on Pye Records, in 1963.
The Turtles recorded a version on their debut album, It Ain't Me Babe (1965). They also released it as a single in Canada (Quality 1791) in January 1966.
Wes Montgomery included a version of the song in his album Goin' Out Of My Head (1965).
Chad & Jeremy included the song into their Second album (January, 1965). It was the last track on their last UK LP so it seems to correlate with the song title somehow. They also released it as a single in The US (World Artists 1052) & Canada (Capitol 72239) as "A Very Good Year"
Frank Sinatra on his September of My Years album (1965) and a stripped-down performance on his Sinatra at the Sands live album (1966)
Herb Alpert & the Tijuana Brass included a melancholy instrumental version of the song on their album What Now My Love (1966)
Gábor Szabó recorded a version in his album Spellbinder (1966).
Eddie Harris recorded a version in his album Mean Greens (1966).
William Shatner did a spoken-word cover of this song interspersed with lines from Hamlet on his album The Transformed Man (1968).
Lou Rawls covered this song in 1966, produced by David Axelrod and included on his hit album Soulin' as part of a "Memory Lane" medley. Rawls also performed it just before his death on 2006's "An Evening of Stars" telethon, backed by the Rickey Minor Band.
Harry James released a version in 1967 on his album Our Leader! (Dot DLP 3801 and DLP 25801).
Lennie Hibbert included this as the last song on the album "Creation" (Studio One) mislabeled as "Nature Boy. " The brilliant Jackie Mitoo organ instrumental is accompanied only by hand drums.
Boris Karloff performed a moving rendition of the song on The Jonathan Winters Show in 1968, at the age of 80.
Rowan & Martin's Laugh-In did a skit wherein Dan Rowan changes army uniforms from World War II, Korea, and then Vietnam as the song plays in the background.
In 1971, Michael Jackson sang a parody of this song in a skit with Diana Ross during the Diana! TV Special.
Baden Powell recorded an instrumental version of it, titled "It Was A Wonderful Year", on his album Grandezza on Guitar (1971)
Della Reese performed the song at the Playboy Club in Chicago and was later featured on her LP, One More Time!.
In the 78th episode of The Muppet Show, Statler and Waldorf performed the song from their box.
British pop star Robbie Williams recorded a version for his album Swing When You're Winning (2001), in duet with Sinatra's original vocals. The instrumental track was also sampled from Sinatra's original recording.
Frank Sinatra's version of the song was featured in the Spike Lee film Jungle Fever (1991).
In a 1993 episode of The Simpsons ("Duffless"), Homer sings a parody of this song entitled "I Drank Some Very Good Beer", recounting the first beer he ever purchased (with a fake ID; his name was Brian McGee) and he "stayed up listening to Queen."
The Flaming Lips covered this song on the compilation Chairman of the Board (Interpretations of Songs Made Famous by Frank Sinatra) (1993).
The Reverend Horton Heat covered the song in 2000 and released it as a single to promote the album Spend a Night in the Box (2000).
It has been adapted in French, as "C'était une très bonne année", by Robert Charlebois on his album Doux sauvage (2001).
Paul Young included a cover version on his album The Essential Paul Young (2003)
Ray Charles covered the song (as a duet with Willie Nelson) on his album Genius Loves Company (2004).
In 2005, They Might Be Giants parodied this song on their first ever podcast.
An instrumental version appears on the album Big City (2005) by Dave Stryker.
Gordon Goodwin's Big Phat Band recorded a version for the album The Phat Pack (2006).
Irish folk singer/songwriter Ronnie Drew included a coverversion of the song on his album There's life in the old dog yet (2006)
Brett Anderson sang it live as can be heard on the album Live at Queen Elizabeth Hall (2007). At the end of the song Brett jokingly says that he wrote it last night.
Dee Snider of Twisted Sister recorded a version for the album SIN-atra (2011), a heavy metal cover album of Frank Sinatra songs
A recording was included on Alfie Boe's album Alfie (2011).
Alain Resnais used the Sinatra recording over the closing credits of his film You Ain't Seen Nothin' Yet (2012). The song plays no role in the film proper, but in You Ain't Seen Nothin' Yet (French title: Vous n'avez encore rien vu) has similar themes and tone of autumnal reminiscence as the Sinatra recording — a dead stage director invites his actors to a wake and performance of a play they all had acted in for him.
Shirley Bassey recorded it on her album Hello Like Before (2014), produced by Stuart Barr.
Mel Torme hosted a 1971 summer replacement television show named after the song, using it as open and close music
