"Gambler" is a song by American singer Madonna from the soundtrack album to the 1985 film Vision Quest. The song was written solely by Madonna, while the production was handled by John "Jellybean" Benitez at her request. It was released as the second single from the film's soundtrack album in September 1985, by Geffen Records. "Gambler" was never released in the United States, at the request of Madonna's own Sire Records. The music video of the song is an excerpt from the film.

Musically, "Gambler" is an upbeat synthpop and disco song, featuring instrumentation from drums, electronic handclaps and percussion, which is accompanied by a bass synth and keyboards. The lyrics talk about Madonna asserting her self-independence. Critics gave a mixed review of the song, but it was commercially successful, reaching the top-ten in the charts of Australia, Belgium, Ireland, Italy, Netherlands, Norway and the United Kingdom. Madonna has performed the song only once, on her 1985 The Virgin Tour, which was documented on the live video release Madonna Live: The Virgin Tour.

After the recording of "Crazy for You", the soundtrack single for the 1985 coming of age drama Vision Quest, Madonna approached John "Jellybean" Benitez to produce another of her self-written songs called "Gambler". Subsequently, the song was added to the soundtrack of the film, as music producer Phil Ramone felt that it would be appropriate for using in the beginning shots of the film. Madonna explained that the track "is really the girl's point of view, because she's, like, an unstoppable person... She doesn't really need this guy". As the song was recorded on the Geffen label, a commercial issue of the single, in the United States was suppressed, at the request of Madonna's Sire Records management. They feared that commercial availability of another Madonna single would have been detrimental to the other singles from the Like a Virgin album, and the already available, Geffen-distributed, "Crazy for You". Hence "Gambler" was never released, or sent for airplay in the United States. The UK 12" single, contained the Extended Dance Mix, Instrumental Remix, and the song "Nature of the Beach" by Black 'n Blue. The 7" single had the original version, and "Nature of the Beach". The video for "Gambler" is similar to "Crazy for You", with Madonna singing the song along with clips culled from Vision Quest. Madonna filmed her performance on November 22, 1983, at the Big Foot Tavern in Spokane, Washington. "Gambler" remained Madonna's last single written entirely by herself for over two decades, until "Hey You" (2007). According to Stylus Magazine, Madonna said that she got too lazy to write songs without help.

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