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.
Brad even feels insecure about his own son and being jealous of the boy's future big success in music, showing a depiction of a dark side of human nature but presented with humor. It's good that Austin Abrams manages to hold his own opposite the more veteran Stiller, with his calm presence providing a good chemisty with Stiller's tense and guarded demeanor. Stiller is so adept in portraying his own mood swings that, at times, you want to slap him to knock some sense into his head.
Giving the film a good dose of humor is Shazi Raja as Ananya, a friend of Troy who's also a musician and is already studying in Harvard. She's bright and beautiful and full of life, a reminder to Brad of the kind of person he always wanted to be. She appears only in a couple of scenes but manages to make a good impression on him and also in us viewers.
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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