In James L. Brooks’s new romantic comedy How Do You Know , Owen Wilson co-stars as a loopy, commitment-phobic major league pitcher who romances Reese Witherspoon’s character (to the best of his ability) during a low point in her career. How did Wilson get to a point in his career where he is acting opposite Oscar winners (Witherspoon, Jack Nicholson) in an Academy Award-decorated scribe’s script? Movieline charts the eight roles that lead Owen Wilson to this point.

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8 Milestones in the Evolution of Owen Wilson
























