A struggling writer and wine enthusiast, Miles (Paul Giamatti) and his engaged college buddy Jack (Thomas Haden Church) embark on a trip to California, planning to explore wine country as a bachelor-party bonding experience.
While Miles wants to relax and enjoy a drink, Jack is in search of a fling before his wedding – but when the two meet Stephanie (Sandra Oh) and Maya (Virginia Madsen), they find themselves exploring their failures and questioning their friendship.
Perhaps writer-director Alexander Payne's best-loved comedy, this typically bittersweet road movie goes down as smoothly as any good glass of wine. (Just make sure it's not Merlot.)