The 20 Weirdest Celebrity Couples Ever

8. Owen Wilson and Sheryl Crow

This one just seems unexpected. You wouldn’t expect these two to run in the same circles or have that much in common. However, their relationship must have been a good one, because it ended on amicable terms. They broke up in 2002, and later that same year, Sheryl was still singing his praises. In his own right, Owen has had nothing bad to say about Sheryl either.