To say that Fiona Apple was attracted to the quirky type is probably an understatement. She and six-time Oscar nominee Paul Thomas Anderson have been lovingly called the "coolest, dorkiest, sexiest, and most indelible celebrity power couple of the '90s," a statement we will gladly cosign. Not only did they begin dating in 1997, but Paul and Fiona also collaborated artistically during their joint rise to fame; he directed a number of her music videos, including "Across the Universe," "Fast as You Can," "Limp," and "Paper Bag," and after their 2000 breakup, the two reunited to work on the video for "Hot Knife" over a decade later. Paul is now married to SNL alum Maya Rudolph, but he and Fiona have remained civil — "Paper Bag" was even featured in Maya's hit comedy Bridesmaids in 2011.