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 stairs"; 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. The song written by Ervin Drake actually was inspired by his future wife to be Edith Vincent Bermaine. She was a showgirl who he dated, and thirty years later married.
The Turtles recorded a version on their debut album, It Ain't Me Babe. Also released as a single in Canada (Quality 1791) in January 1966.
Wes Montgomery included a version of the song in his 1965 album Goin' Out Of My Head.
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"
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.
Boris Karloff performed a moving rendition of the song on The Jonathan Winters Show in 1968 at the age of 80.
British pop star Robbie Williams recorded a version for his 2001 album Swing When You're Winning, in duet with Sinatra's original vocals. The instrumental track was also sampled from Sinatra's original recording.
The song was featured in the 1991 Spike Lee film Jungle Fever.
In a 1993 episode of The Simpsons, 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 in 1993 on the compilation Chairman of the Board (Interpretations of Songs Made Famous by Frank Sinatra).
Irish folk singer/songwriter Ronnie Drew included a coverversion of the song on his 2006 album "There's life in the old dog yet"
It was used as the opening song in the second season premiere of the HBO drama The Sopranos. The entire Sinatra recording is played while the viewers see how things have gone since the previous season ended. There is no dialog.
In 2007 Brett Anderson sang it live as can be heard on the album Live at Queen Elizabeth Hall. At the end of the song Brett jokingly says that he wrote it last night.
In 2011 Dee Snider of Twisted Sister recorded a version for the album SIN-atra, a heavy metal cover album of Frank Sinatra songs
In 2011 A recording was included on Alfie Boe's album Alfie.
Alain Resnais used the Sinatra recording over the closing credits of his 2012 film You Ain't Seen Nothin' Yet. 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.