Madonna: Papa Don't Preach (1986)

It is among several contenders for Madonna's most controversial song. 1986's Papa Don't Preach set the Bible Belt on fire with it's focus on teen pregnancy and may have caused more of a ruckus with the moral majority than her pointed brazier.



One of the flagship singles from the immensely popular True Blue album, the music video co-starred Danny Aiello (The Last Don, The Professional) as Madonna's distressed father, trying to come to terms with her situation and decision.



The song was covered almost 20 years later by Ozzy Osbourne's kid Kelly. Although you have to wonder what Ozzy Osbourne could preach to his children not to do, with any credibility.



And here's the live version...

Madonna: Dress You Up (1985)

It stands as one of Madonna's most remixed songs and possesses a quiet "staying power" that has allowed it to endure despite not being one of her highest selling singles. Dress You Up was released as a single from the Like a Virgin album in 1985, peaking at #5 on the Billboard Hot 100 chart even though it never enjoyed the benefit of having an official video made to accompany it.

Here is a live performance of the song from the Virgin Tour in 1985, which ultimately served as the de facto video.



And here is a fusion of the song with Material Girl from the 1987 Who's That Girl tour. This was, in fact, the last tour during which the song was performed by Madonna as part of a concert set.



One of the more unique unofficial arrangements is the following Forever in Love Remix...



Finally, and this was met with a mixed reception at the time, here is a sample of the Gap's 1990s Dress You Up ad campaign. Some thought it was trendy and fashionable. Others thought a dance classic was being murdered with a cheap gimmick. And others still were simply happy to have one of their favorite Madonna songs dusted off and appearing between segments of Melrose Place.