Captain Jack

This song is based on a real person who was a drug dealer that lived near Joel in Oyster Bay, New York, but as the singer explained in a 1975 interview with ZigZag, the character "Captain Jack" was a composite of different kinds of people. Said Joel: "I was just sitting around one day looking out of the window wondering what I was going to write about, and kinda wrote about what was going on outside. I mean, Long Island is a suburb and it was about a suburban type of character. There's a lot of frustration living in the suburbs - you don't have an identity as you would if you came from the city or the country, there's city music and there's country music, but there's really no suburban music, you kinda copy the city. You have both influences pulling on you."

Joel considers this an anti-drug song, as he sings about how their users become apathetic and lifeless. Before playing this at concerts, Joel has explained to the audience that the song is about spoiled, lazy, apathetic young college students who don't care about much other than partying and having sex; their family has money and paid for them to receive a good education, but they toss it away and don't care for anything except 'good ol' Captain Jack.'

While many songs contain references to masturbation (check out "She Bop" or "Whip It"), this is one of the few that actually uses the word "masturbate" in the lyrics. This, along with the marijuana references, kept it off the playlists at most radio stations.

In 1973, Joel got a contract with Columbia Records after the Philadelphia radio station WMMR started playing a live version of "Captain Jack" from a show the station sponsored a year earlier. Joel wrote the song about a year before he recorded it on Piano Man.

Joel is a prolific hitmaker, but many of his lesser-known songs became fan favorites even though they were not commercially successful. Many of these songs, including this one, appeared on Joel's 1981 live album Songs In The Attic.

This was played at Hillary Clinton's official announcement for her Senate run in 2000. Her opponent, New York City mayor Rudy Giuliani, claimed that by playing this she was supporting drug use. In a blatant case of political grandstanding, Giuliani called a news conference and read some of the song's more offensive lyrics. Clinton's people didn't mean to play the song: they played "New York State Of Mind" but left Joel's Greatest Hits album on too long.

John Kalodner quoted Joel's explanation of this ballad about the "lost" affluent suburban youth in a review for Concert magazine in 1974. Said Joel: "It's about coming out of the New York suburbs, but in my travels I have seen a lot of the same suburb all over the country. The song is sort of brutal, but sometimes it is good to be brutal and offend people - it keeps them on their toes."