Failed novelist and wine enthusiast Miles (Paul Giamatti) takes his engaged friend Jack (Thomas Haden Church) on a trip to wine country for a last single-guy bonding experience. While Miles wants to relax and enjoy the wine, Jack is in search of a fling before his wedding—with predictably disastrous results. With its witty, award-winning script and hysterical performances, Sideways is a classic odd-couple comedy that somehow manages to be anything but formulaic. As the two friends act out middle-aged panic in radically opposite ways, they learn bittersweet lessons about their deepest selves. Sit back and enjoy with a good glass of pinot noir—but god forbid you reach for the merlot.
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Want more? Check out Watch List: In It to Win It. Lovable underdogs are the stars of a specially curated series we’ve put together to celebrate the theatrical premiere of Blind Ambition.
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