Run time: 122 mins

Wine, women and wonder reignite the lives of two former college roommates in Alexander Payne’s lovable modern classic.


One week before Jack gets married, best friend Miles takes him to Santa Ynez Valley, with wine-tasting and a few rounds of golf in mind, but Jack wants to have a last-minute fling or two before he settles down. Both men are just hitting midlife; Miles is a middle school English teacher who’s never published that elusive novel and Jack’s a struggling actor whose greatest claim to fame is a TV advert voiceover. When they meet two fascinating, intelligent women, their holiday takes a turn.


Miles Raymond, brilliantly played by Giamatti, is the sort of intellectual loser often found in the works of Woody Allen. He’s the perfect foil to Haden Church’s has-been soap actor as they stumble through a week’s vacation amidst the well-lit banality of California. Their companions for the week aren’t too shabby either, with outstanding supporting turns from Sandra Oh and Virginia Madsen making up a the quartet.


A richly entertaining, thought-provoking and moving film, Sideways is an absolute masterclass in classical cinematic storytelling and, as it approaches its 20th birthday, remains one of the finest American films of the 21st century.


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