First Hit #1: August 22, 1987
I’m going to be so bold as to say Madonna’s best songs and her biggest hits aren’t generally the same thing. As evidence, let’s take Who’s That Girl, which is an okay song. Alright, that’s not being completely fair, it’s got a pretty decent Caribbean-inspired beat and an okay vocal performance overall. We even get some Spanish thrown in, for the sake of it. It’s a pretty decent soundtrack for lounging around in the summer doing nothing in particular. Yes, if I look out my window all I see is snow, but it has a nice, sunny vibe that I can get behind.
That said, it’s also an incredibly minor song. It’s mostly just repetitions of the title, which happens to be a movie Madonna was starring in at the time. The Spanish section may as well have said “In theaters, this summer,” since it’s just as much about promoting the new film as it is about giving a summer vibe. And that’s the thing, it’s an okay song, but Madonna had plenty of better songs out there which never ascended to the top spot. It’s the minor stuff that brings her major success it seems.