Best known for: Rayna James, Nashville (ABC)
Weirdest role: Madeleine, Cupid (1998)
Have you been aching to see Connie Britton and Jeremy Piven light up the screen together? Neither have we! This onscreen pairing was a reality for a brief, shining moment in the 1998 television show, Cupid. In Cupid the man behind Ari Gold played an exiled version of the mythical matchmaker who must unite 100 couples if he wants to earn his way back to Olympus. This was a real thing. Rightfully short-lived, but real nevertheless.