Critics Consensus

Charming, thoughtful, and often funny, Sideways is a decidedly mature road trip comedy full of excellent performances.



Reviews Counted: 228

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User Ratings: 197,574


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Reviews Count: 0
Fresh: 0
Rotten: 0


Average Rating: 3.4/5

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Movie Info

A wine tasting road trip to salute Jack's final days as a bachelor careens woefully sideways as he and Miles hit the gas en route to mid-life crises. The comically mismatched pair, who share little more than their history and a heady blend of failed potential and fading youth, soon find themselves drowning in wine and women. Emerging from a haze of pinot noir, wistful yearnings and trepidation about the future, the two inevitably collide with reality.

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Sandra Oh
as Stephanie
Jessica Hecht
as Victoria
Alysia Reiner
as Christine Erganian
Shake Toukhmanian
as Mrs. Erganian
M.C. Gainey
as Cammi's Husband
Marylouise Burke
as Mile's Mother
Duke Moosekian
as Erganian, Mike
Robert Covarrubias
as Mile's Building Manager
Patrick Gallagher
as Gary The Bartender
Stephanie Faracy
as Stephanie's Mother
Joe Marinelli
as Frass Canyon Pourer
Chris Burroughs
as Chris At Sanford
Toni Howard
as Evelyn Berman-silverman
Lee Brooks
as Ken Cortland
Peter Dennis
as Leslie Brough
Alison Herson
as Foxen Winery Pourer
Phil Reeves
as Vacationing Dr. Walt Hendricks
Robert Trow
as Obnoxious Golfer
Lacey Rae
as Los Olivos Waitress
Daniel Rogers
as Reciting Eighth Grader
Simon Kassis
as Mini-mart Owner
Sevag Kendirjian
as Armenian Deacon
Heghine (Helen) Harboyan
as Wedding Vocalist
Gohar Toranyan
as Wedding Organist
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News & Interviews for Sideways

Critic Reviews for Sideways

All Critics (228) | Top Critics (50)

Audience Reviews for Sideways


Giamatti's manic self-loathing is the films' greatest aspect, but Payne has written and directed a mature and humorous drama.

Kase Vollebregt
Kase Vollebregt

Super Reviewer



Directors Cat
Directors Cat

Super Reviewer

Engaging, well-paced, and ultimately satisfying, Sideways is an enjoyable, well-acted comedy that features tender moments, strong writing, and subtle humor.

Matthew Samuel Mirliani
Matthew Samuel Mirliani

Super Reviewer


Humanistic, comedic, dark and bittersweet, Sideways is a film that is temporarily moving, and has certain staying power. It creates a fracas, as two best friends see the underbelly of the middle of their lives, while preparing for marriage, the beginnings of a life after divorce, and despairing over the evils of old age. Buddies Miles and Jack road trip to wine country, which ferments the rest of the film in a drunken regard. Between showing drunk Miles pitching away his life again and again, at the bottom of a wine glass, and Jack throwing himself at every woman who moves, it's a nice contrast between two pathetic men showing their true colors in different ways. Giamatti is certainly one of the best character actors of his generation and shows his resolute grace in a role that was made for a sad sack with a penchant for the dramatic. The two friends seem unevenly matched, as Jack wants to be a wild child in the heart of California country, while Miles wants to golf, taste the wine, and bask in sophisticated luxury. They bicker as an old married couple and each gets stranded along the way in their own self-pity and gluttony. Once their female companions (Virginia Madsen and Sandra Oh) enter the fray it becomes a love story, one that is awkward and slow, but real and heartbreaking. Between Giamatti and Madsen is the greatest friction and watchability. I couldn't quite get behind Jack (Thomas Hayden Church) who flees from his infidelities with such pathetic irony that it's hard to keep listening. Giamatti comes out the victor of the film, the only one to gain any pride or closure from the trip, or his plight for self-discovery. It's a film about the chances we take and the decisions that bring us happiness rather than self-implosion.

Spencer S.
Spencer S.

Super Reviewer

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