Graham Parker should have been really big but hardly anybody remembers him now or if they do remember him, it's as "that guy that sounds kind of like Elvis Costello." The Rumour were a great band too, they really should be remembered better than that. http://www.youtube.com/watch?v=4C2SkcC3TXc
Pentagram was a great 70s hard rock band influenced by Sabbath and Blue Cheer - got off to a really promising start with some amazing demos, but they had internal problems (drugs, etc.) and never went anywhere really; quickly turned into just a niche act for underground metalheads. I consider their best material almost as good as Sabbath, but they're like 1% as well-known. http://www.youtube.com/watch?v=c7JTD_73kpI
Cyndi Lauper is one of my favorite what-ifs. Remember when her and Madonna were competitors? Madonna won the war devastatingly, but Cyndi was a better singer with more personality (not just sex-doll personality) and picked better songs, to my ears. But she wasn't a career girl like Madonna was. I think to a lot of people now she's viewed as a one-hit wonder, pretty much. Weird to call a person who was THAT successful unsung, but in a way she was. I still dig this song, which was her comeback hit (it was a brief comeback): http://www.youtube.com/watch?v=2y1TZXc5DiY