So many choices here! The song below always reminds me of a high school classmate of mine, Trini Triggs.
For those too young to remember, this was a hugely controversial song in 1984. It inspired Tipper Gore to found the Parents’ Music Resource Center and the ensuing Congressional circus over obscenity in pop music. Our journalism teacher hadn’t heard the song and asked what the deal was about it, so Trini sang it for the whole 10th grade journalism class. (We had all heard it, of course; the teacher was momentarily shocked by the “masturbation” line, but not really offended.) It didn’t hurt that Trini looked a little bit like Prince, a short, light-skinned black guy with an AWESOME Jheri curl. Trini was a successful singer in high school and in local bands, and has even had minor success as a country music artist. I’ve linked to one of his videos in the past; here’s another.