When Will Smith’s movie career exploded, initially he kept his rap career going steady right beside it, this time as a solo artist (he was originally the Fresh Prince alongside Jazzy Jeff). The success of MeninBlack in particular led to WildWildWest, a movie that proved there were limits to his appeal. But the song was still good!
Here’s another I can’t believe I didn’t include earlier. I became a hopelessly devoted fan of Warren Zevon very, very late in his career, when David Letterman invited him on in his last days. But I guess in my family I was the only one to listen to “Werewolves of London” as a kid and remember it fondly. It was a classic for me, no idea when or how I originally heard it. Still can’t believe the rest of the world hasn’t caught up with his genius.