Owen Wilson stars in this comedy as slacker Randy Dupree, best man to his friend Carl (Matt Dillon) at his recent wedding to the beautiful Molly (Kate Hudson). As Carl and Molly settle down to married life, their newlywed bliss is rudely interrupted when Dupree reveals that he's lost his job, his house, and even his car, all because he took the time off for Carl's wedding. Crashing in their spare room, Dupree's outrageous antics soon test Carl's notions of friendship to the limit.