Valentine's Day

Album: Never Die Young (1988)
Play Video

Songfacts®:

  • A gentle James Taylor song called "Valentine's Day" seems like a great addition to that mixtape you're putting together for that special someone on the Hallmark holiday, but we'd advise against it. It starts off whimsical, with "fishy love," but then we start hearing about Al Capone, Bugs Moran, gin, and porkpie hats. Indeed, the song is about the Saint Valentine's Day Massacre of 1929, when seven Chicago gangsters were gunned down. Belying the melody, this is a rather dark song about it.

    Taylor told the story behind the song in 1997 on his second episode of VH1 Storytellers.

Comments: 1

  • Brad Broenen from Hopkins, MnAlthough the song mentions the St. Valentine's Day Massacre, it does so metaphorically. If you listen to the WHOLE SONG, it is obviously about a couple arguing and consequently breaking up on Valentine's Day.
see more comments

Editor's Picks

Tommy James

Tommy JamesSongwriter Interviews

"Mony Mony," "Crimson and Clover," "Draggin' The Line"... the hits kept coming for Tommy James, and in a plot line fit for a movie, his record company was controlled by the mafia.

Steely Dan

Steely DanFact or Fiction

Did they really trade their guitarist to The Doobie Brothers? Are they named after something naughty? And what's up with the band name?

David Gray

David GraySongwriter Interviews

David Gray explains the significance of the word "Babylon," and talks about how songs are a form of active imagination, with lyrics that reveal what's inside us.

JJ Burnel of The Stranglers

JJ Burnel of The StranglersSongwriter Interviews

JJ talks about The Stranglers' signature sound - keyboard and bass - which isn't your typical strain of punk rock.

Tim McIlrath of Rise Against

Tim McIlrath of Rise AgainstSongwriter Interviews

Rise Against frontman Tim McIlrath explains the meanings behind some of their biggest songs and names the sci-fi books that have influenced him.

George Clinton

George ClintonSongwriter Interviews

When you free your mind, your ass may follow, but you have to make sure someone else doesn't program it while it's wide open.