Release Year: 2008
Costume Designer: Susan Matheson
Who vs. Who: Brennan Huff (Will Ferrell) vs. Dale Doback (John C. Reilly)
Will Ferrell and John C. Reilly's 40-year-old slacker characters in Step Brothers certainly look like they've yet to grow up. Dig through your old childhood photo albums and, odds are, there are some loudly colored T-shirts to be seen, most likely purchased during trips to the seashore. Ron Jon Surf Club, anyone? Hysterical.