I'll Remember...1985

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.   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.  To date, "Gambler" remains the last self-written Madonna single.


"Gambler" was released in October 1985 in the United Kingdom, and debuted at position twenty on the UK Singles Chart. After two weeks, it peaked there at four, and was present for 14 weeks. By the end of 1985, Madonna chalked up another record with the song, becoming the first female artist to have eight UK Top 10s in one calendar year. The song was certified silver by the British Phonographic Industry (BPI) for shipment of 200,000 copies of the single. According to The Official Charts Company, the song has sold 295,000 copies there. In Australia, the song debuted on the Kent Music Report chart at 14, and reached a peak of ten. In Germany, the song debuted at 39 on the Media Control Charts, and reached a peak of 25 after five weeks, being present on the chart for 12 weeks.  Across Europe, the song reached the top-ten of the charts in Belgium, Ireland, Italy, Netherlands and Norway. It peaked at 12 in Japan, 23 in Switzerland and 45 in New Zealand.

Madonna has only performed this song live once, on her 1985 The Virgin Tour. It was the first song, of the second act of the show. Madonna wore a black, fringed micro-top and similar skirt, with her belly-button exposed, and a number of crucifixes in different sizes, hanging from different parts of her body. As the guitar intro of the song started, Madonna appeared on the side-stage and started dancing energetically, while flashlights fell on her. While singing the song, she sometimes opened her jacket and sometimes straddled the steel structure present on the stage. The performance ended with Madonna jumping off the side stage, onto the main stage. It was included on the video release, titled Live – The Virgin Tour, which was shot in Detroit.