Owen Wilson

One of the most iconic Hollywood actors of our generation, Owen Wilson, is known for such hits as Marley & Me, Wedding Crashers, and Disney’s Cars. The actor started his career with Bottle Rocket, a movie he co-wrote alongside filmmaker Wes Anderson, which turned out to be both of their debut film in 1996. With his Hollywood breakthrough, he was able to land a minor role in The Cable Guy, which in turn paved his way to his eventual 2000 smash-hit film Shanghai Noon alongside Jackie Chan. This led him to amass an impressive degree of fame.

Around this time, the now-famous actor’s love life entered the spotlight. A year before, he was dating the American musician Sheryl Crow, with their relationship ending in 2001. Fast-forward to 2021, the single father to three has amassed a rather large list of ex-girlfriends. His most notable was his relationship with fellow You, Me, and Dupree star Kate Hudson. They dated starting from 2006 until they called it quits in 2009. The pair has since then reconciled and become rather close friends.