Brad has quite a pleasant life in California with a non-profit company he formed, whose aim is to help other non-profit companies get funding. He has a loving and perky wife, Melanie (Jenna Fischer), but it's not at all good enough for him compared to what he thinks his college friends have achieved. Jason (Luke Wilson) is a hedge-fund manager who travels all over the world. Nick (Mike White, who directed the film himself) is a well known director in Hollywood. Billy (Jemaine Clement) is a gentleman of leisure in Hawaii after selling his own software company and retiring at the age of 40.
But the most successful in Brad's own estimation is Craig (Michael Sheen), a respected writer and scholar who teaches at Harvard. He realizes he needs a favor from Craig and this leads to one of the movie's most satisfyingly acted scene. Director Mike White manages to efficiently paint detailed character portraits of these guys, including who they truly are compared to Brad's inflated estimations of them, which he learn from his voice over narrations. At first, it sounds like a bit unnecessary, but we eventually realize that the interior monologues are meant to elucidate the difference between Brad's own perceptions and insecurities vis-a-vis what is reality.
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She is not afraid to tell Brad her own assessment of him and in the end, Brad's status might not have changed drastically, but there is some hope that he will exert more effort to count his blessings and be more thankful with what he already has, especially his supportive wife, his very talented son and his own career that is dedicated to help other people.
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