Movies like Sideways

This Sofia Coppola-directed film shares Sideways' sense of humor, languor, and melancholy. It captures the unlikely friendship and emotional connection between two Americans feeling out of place in Tokyo.

Directed by Alexander Payne, the same filmmaker behind Sideways, The Descendants shares a similar blend of humor and heartache. George Clooney stars as a land baron trying to reconnect with his daughters after his wife is injured in a boating accident, leading to a journey of self-discovery.

Featuring a dysfunctional family on a road trip, Little Miss Sunshine is a bittersweet comedy-drama with heart. Its ensemble cast and offbeat humor make it a film that fans of Sideways would appreciate.

Chef tells the story of a professional chef who starts a food truck journey to reclaim his creative promise, much like the characters in Sideways who seek to redefine their lives. It's a feel-good tale of passion and culinary delight, with a touch of humor.

Starring Russell Crowe as a London-based investment broker who inherits a vineyard in France, A Good Year delves into themes of lifestyle change and self-discovery amidst a scenic backdrop, reminiscent of the wine-tasting journey in Sideways.

Another poignant film from Alexander Payne, About Schmidt follows a retired insurance actuary who embarks on a road trip to stop his daughter's upcoming marriage. Along the way, he faces profound personal questions, much like the characters in Sideways.

Filtered through Alexander Payne's characteristic humanism, Nebraska combines humor with the bittersweet. An aging father and his estranged son travel to claim a million-dollar sweepstakes prize, revealing complexities of family and ambition.