5. Randolph Dupree (You, Me and Dupree)
Dupree (Owen Wilson) is fired for attending his friend Carl's (Matt Dillon) wedding to Molly (Kate Hudson) without getting official permission from his workplace. As a result, he finds himself unable to pay the rent required on his house and is evicted. Finding himself homeless, Dupree is offered refuge in the house of the newly-wed couple by Carl, much to the chagrin of Molly. This leads to a series of hilarious consequences. Dupree's general naivety makes his mere presence on screen a funny thing to behold, while events such as being caught masturbating using one of Carl's socks and setting fire to the couple's home make matters funnier. Ultimately, Dupree sorts his life out and becomes a motivational speaker and author, encouraging people to embrace their ness in order to live life to the full.
Quote:"I've wracked my little Duprees!"