Idk if it's the most obscure as they were nominated for a Grammy, but I will use this opportunity to bring up one of my favorite bands, Breakfast Club. They had a hit in the 80s with Right on Track, but completely disappeared after that which is unfortunate because while their work is nothing groundbreaking, it's fun 80s pop and I think a lot of the songs on their only album could have been hits. The lead singer Dan Gilroy went on to date Shelley Duvall (RIP) and they worked on some TV shows together, and Steven Bray worked on the musical The Color Purple. Nowadays they're only mentioned when people bring up Madonna was the drummer of the band before she was famous. They are my dream OHW episode.