Brad Sloan (Ben Stiller) has a satisfying career and a comfortable life in suburban Sacramento where he lives with his sweet-natured wife, Melanie (Jenna Fischer), and their musical prodigy son, Troy (Austin Abrams), but it’s not quite what he imagined during his college glory days. Showing Troy around Boston, where Brad went to university, he can’t help comparing his life with those of his four best college friends: a Hollywood bigshot (Mike White), a hedge fund founder (Luke Wilson), a tech entrepreneur (Jemaine Clement), and a political pundit and bestselling author (Michael Sheen). As he imagines their wealthy, glamorous lives, he wonders if this is all he will ever amount to. But when circumstances force him to reconnect with his former friends, Brad begins to question whether he has really failed or is, in some ways at least, the most successful of them all.
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