After the True Blue album, Madonna was really trying to light a fire under her movie career. Even though she was busy, she managed to squeak out a few tunes in the next couple of years, from Spotlight (off the You Can Dance remix album), to Causing a Commotion and Who's That Girl? from the movie of the same name. Only the last of that bunch has an official video to my knowledge. And then, Madonna switched gears to the much more serious, much more artistic with Like a Prayer.
The album finally gathered her some respect in the music industry, and marks something of a change in her career from pop singer to artist. There was still controversy, but none of it worked to her detriment. Other songs from the album like Cherish and Express Yourself are video classics.
Madonna finally nabbed a part in a hit movie as "Breathless" in Dick Tracy, and the companion album I'm Breathless produced the quintessential Madonna tune, Vogue. It's a pretty clear dividing line between her early and later work. The Immaculate Collection, a greatest hits collection, had two new hits, most notably the extremely risque Justify My Love. The video was so racy, it got banned from MTV and went on to be the highest selling "video single" ever.
By the time she followed up with Erotica, there was a full-on media onslaught, with her SEX book also hitting the stands. Madonna risked career-killing overexposure. But the music was great. Different, but great. The title track was a little kinky and weird, but it's a good song. The follow-up, Deeper and Deeper has a great double-entendre title (much like the non-hit track, Why it's so Hard).
And with that we'll close the second edition of My Love Affair with Madonna. To read the first part, go here: Blast from the Past: My Love Affair with Madonna (Pt. 1).