Relive the Legend.

It was re-released on CD in the yellow series and in the Japanese 3″ box.

Madonna’s fourth #1 single on the Hot 100 was 1986′s Papa Don’t Preach. It ignited a firestorm over its subject matter (teen pregnancy,) and Madonna’s unabashed video nip-slip. Its maturity and success proved that Madonna was more than a fad. In fact, it topped the Eurochart for 11 weeks.

It was a global hit, reaching the top ten in nearly every country it was released and hitting #1 on Eurochart and the Billboard Hot 100.

Live to Tell has a bit of an interesting history. Patrick Leonard wrote the music hoping to score a job doing the score for the film Fire with Fire. The producers rejected it (and him). He then brought the track to Madonna, who wrote lyrics to it on the spot and recorded a demo. She then took it to the producer of her then-husband Sean Penn’s film At Close Range, who hired Leonard to score that film, instead. She then included it on her True Blue album, along with four other Patrick Leonard collaborations.

After the success of Crazy for You, Gambler was chosen to be the second single from the Vision Quest soundtrack. Madonna’ s regular label objected, so the song wasn’t released in the US. In the UK, it became her 8th top ten song of 1985. A 7″ version featured the B-Side Nature of the Beast (performed by Black N’ Blue,) while the 12″ sported a dance remix and instrumental version.

Gambler is one of Madonna’s least-remembered singles. Take a look look, though. This is the last time we’ll be seeing Madonna as her classic, 80s street kid look. 

Up next: Two more soundtrack singles and then... True Blue.

Variations: 1985 re-release included Into the Groove, which might qualify it as a sixth single. Later reissues have included remixes of Like A Virgin and Material Girl.

The B-Side, as you can see above, was Over and Over.

Here we have an odd situation. There was an official video for Madonna’s cover of Love Don’t Live Here Anymore, but it was released ten years later a remixed form of this same recording. So here’s the original version of the fifth single from Like A Virgin, as it was first released in 1985. If I keep hitting my goal of posting one single per day, we’ll get to that version about a month from now.

Dress You Up hit the shelves on 12″ and 7″ on  July 24, 1985--the day after Into the Groove. The Formal Mix, the Casual Instrumental Mix and Shoo-Be-Doo were the usual B-Sides. It was released on CD as part of the yellow series, in the Japanese 3″ box, and as an EP in Japan with Ain’t No Big Deal as an additional B-Side.

Madonna released a live video for Dress You Up as she turned her attention back toward the Like A Virgin album and The Virgin Tour. (Note that while promoting the album, she released two hit singles that weren’t on it!) It was branded “filthy” by Tipper Gore’s Parents Music Resource Center and became her sixth consecutive US top 5 single.

Stans who misguidedly obsess over chart positions should probably take note that the song wasn’t even eligible to chart at the time of its release, having been a B-Side earlier. It is now her most played song on Billboard’s recurrent airplay chart.

Madonna had appeared in Vision Quest to sing a couple songs, but it wasn’t until Desperately Seeking Susan that she became a movie star. Not all of her future films would be as well-received, but DSS is generally considered to be one of the last classic screwball comedies and Madonna’s soundtrack contribution, Into the Groove, is itself a classic.

It would eventually find its way to CD via the yellow series and Japanese 3″ box.

Angel is probably one of the most overlooked Madonna hits of the 80s. It performed better at the time than many of her signature songs, but for some reason has fallen through the cracks a bit over the years.

The 1991 7″ / CD5 release featured the Q-Sound remix created for its appearance on The Immaculate Collection and Shep Pettibone Single Remix of Keep It Together, while the 12″ version featured longer Shep Pettibone remixes of Keep It Together and Into the Groove. A picture disc was also issued around this time.