This one was a doozy. Whoopi and Ted became friends after meeting as guests on The Arsenio Hall Show in 1988, but it wasn't until they starred together in Made in America in 1992 that a romance blossomed. The one tiny issue was that Ted was married at the time (to his second wife, Cassandra "Casey" Coates), and his affair with Whoopi led to their $30 million divorce. Their relationship survived a racially charged stand-up routine, but they ultimately called it quits in 1993.