Top 20 Strangest Celebrity Couples

3. Val Kilmer and Paris Hilton

This one did not make sense on so many levels — not only was there a 21-year age gap, but they were in two different leagues. Despite not exactly being in his prime, Val Kilmer is a smart man and a very talented actor. Paris Hilton may be pretty buuut there’s little else she has to offer Val Kilmer. He seems to agree, as years after their fling he criticized the media for making her famous for nothing.