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Cast & Crew
Frequently asked questions
What is Sideways about? 
Sideways is a comedy-drama film that follows two middle-aged men, Miles and Jack, on a road trip through California's wine country. Miles, an unpublished writer and wine aficionado, wants to spend the week relaxing and enjoying good food and wine. Jack, a former actor and soon-to-be-married man, is on the prowl for one last sexual fling before settling into domestic life. As they visit various wineries and vineyards, they encounter a cast of colorful characters and find themselves in unexpected situations that challenge their friendship and their views on life, love, and relationships. Nominated for five Academy Awards® including Best Picture, this critically acclaimed film features witty dialogue, engaging performances from Paul Giamatti and Thomas Haden Church, and stunning cinematography of the California coastline.
Where can I stream Sideways? 
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What movies are similar to Sideways? 
Some movies that have similar genres and were produced around the same time as Sideways include Punch-Drunk Love, He's Just Not That Into You, Lost in Translation, Hairspray, No Reservations, Varsity Blues.