On December 22 1985, John “Jellybean” Benitez’ Sidewalk Talk (featuring Madonna) debuted at #48 on the Billboard Hot Dance/Disco chart (not to be confused with the Hot Dance Music/Maxi-Single Sales chart). The hit dance single peaked at #1 on the Dance/Disco chart on February 2 1986.
Sidewalk Talk was written by Madonna, arranged by Jellybean and Stephen Bray and mixed by Jellybean.
On October 18 1986, Madonna’s True Blue debuted at #27 on the Billboard Hot 100 Single Sales chart. True Blue spent 10 weeks on the chart, eventually peaking at #4 on November 15.
On October 3 1985, Geffen Records released Gambler as a single in Europe. It was the second Madonna single released from the Vision Quest soundtrack.
Concerned about potential overexposure, Warner Brothers successfully managed to suppress a North American release of the track, although the music video was serviced to MTV. It was issued as a single in most other major markets – including Japan, Australasia & South America.
Gambler was written by Madonna, produced by Jellybean Benitez and arranged by Stephen Bray. Extended and instrumental remixes by Benitez were also issued commercially outside North America.
On September 10 1986, True Blue was released as a single in Canada. Written & produced by Madonna & Stephen Bray, the title-track of her third album was a 1960’s Motown-inspired love letter to her husband, Sean Penn.
After including True Blue on 1987’s Who’s That Girl World Tour set list, the song appeared to have been written out of Madonna’s repertoire following her split from Sean. By 2015’s Rebel Heart Tour, Madonna had made amens with both Sean and True Blue, performing the track as a stripped-down, crowd-pleasing acoustic number.
Shep Pettibone’s remixes of the single marked his first of many collaborations with Madonna.
On July 23 1985, Into The Groove was released as a single in the UK.
Not wanting to draw more attention away from the Like A Virgin album following the release of the soundtrack hit Crazy For You, Sire/Warner notoriously relegated Into The Groove to the b-side of the Angel 12″ single in North America & Australia, although they eventually ceded to issuing it as an A-side in most other international territories.
Into The Groove was written & produced by Madonna & Stephen Bray and was their first released co-production to not be reworked by an outside producer (the pair had already been producing their own demos for years). The original demo version was used over the closing credits of Desperately Seeking Susan (seemingly dubbed from an actual cassette copy of the demo–granted, DAT’s were still a few years away), and although the commercially released mix featured a slightly beefed-up and more polished-sounding musical backing track, it kept Madonna’s original demo vocals intact.
In the UK, and throughout most of Europe, the single was backed by the Madonna-penned ballad Shoo-Bee-Doo, while the original album version of Everybody (another song credited to her alone) rounded out the 12″ single…it would be fair to assume that Madonna likely earned some of the biggest single-generated songwriting royalty cheques of her career thus far with this release. It’s interesting to note that despite being one of Madonna’s most enduring dance floor classics, no remixes were produced for Into The Groove at the time of its release. It wasn’t until 1987’s You Can Dance remix compilation that the song finally received an official extended remix treatment.
On February 15 1985, the Vision Quest original motion picture soundtrack was released on Geffen Records. To promote the release, music videos for Crazy For You and Gambler premiered on MTV on the same day.
Despite Gambler only being released as a single in markets outside North America, its video received moderate rotation from MTV nonetheless – possibly due to the fact that there were no competing videos produced for the final two singles from Like A Virgin.
Gambler was Madonna’s last entirely self-written single until the 2007 release of the charity single, Hey You. Other singles for which she received sole writing credit include Everybody (which was in fact a Stephen Bray co-write–however a publishing arrangement granted him sole credit for another of their collaborations, Ain’t No Big Deal, in trade), Burning Up, Lucky Star and Sidewalk Talk. Album tracks Think Of Me, I Know It and Shoo-Bee-Doo were also entirely self-written.
A third Madonna song that was recorded for the Vision Quest soundtrack, Warning Signs, was eventually dropped from the project. A cassette copy of the song, which is also credited to Madonna alone, was submitted to the Library of Congress for copyright registration in February of 1984, at the same time as Gambler.
With Stephen Bray having confirmed his involvement in the song’s production (which he described as “a cool synth track”), it appears that its production credits would mirror those of Gambler, which was produced by Jellybean Benitez and arranged by Bray. Given that early press for Vision Quest (including an on-set interview with Madonna herself) mentioned the inclusion of three new songs, footage of Madonna performing Warning Signs was likely filmed but ended up on the cutting room floor. Surprisingly, this additional footage has never resurfaced and the song has never leaked.
On September 26 1988, Madonna began recording the Like A Prayer album in Los Angeles, California with collaborators Patrick Leonard and Stephen Bray.
Madonna had begun writing for the album during down time of her Broadway run in David Mamet’s Speed-The-Plow, for which she gave her final performance in late August. With her marriage to Sean Penn on the rocks, Madonna found herself at a personal and creative crossroads–with plenty to express.