Hollywood Flashback: When ‘Sideways’ Was the Toast of Awards Season

Alexander Payne and Paul Giamatti’s latest film, The Holdovers, is in the awards conversation for its tale of holiday mischief and misfits at a remote New England boarding school. In it, Giamatti plays a cranky history teacher tasked with looking after students who aren’t going home for winter break. Almost 20 years ago, Payne and Giamatti earned awards acclaim for their first collaboration: 2004’s Sideways.

For Giamatti, who had built a career as a character actor, the film marked his second as a lead (after American Splendor the year before). He plays Miles, a depressed middle-aged English teacher, unpublished writer and wine snob on a vineyard-hopping road trip through California’s Santa Ynez Valley with his friend Jack (Thomas Haden Church), a down-on-his-luck actor about to get married. Payne and co-writer Jim Taylor adapted the screenplay from Rex Pickett’s novel of the same name and filmed on location at hotels, restaurants and wineries in Santa Ynez, Solvang and Buellton. (The Days Inn in Buellton rebranded itself the Sideways Inn after the movie’s success.) Virginia Madsen and Sandra Oh round out the cast as Maya and Stephanie, respectively, the two love interests for the traveling duo.

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THR’s review out of the Toronto Film Festival raved, “This hysterically funny yet melancholy comedy … has a beautiful structure, buoyant bouquet of risky romance, a fine balance between its seemingly loose sequence of events and tight control of dramatic subtext,” and noted of the two protagonists: “You could watch these two guys comically screw up forever.”

Many critics associations agreed, including the Broadcast Film Critics Association, which honored Sideways with five Critics Choice Awards: best picture, screenplay, supporting actor for Haden Church, supporting actress for Madsen and acting ensemble (which recognized all four of the film’s key players). The film went on to win Golden Globes for best picture, musical or comedy, and best screenplay, and the Oscar for best adapted screenplay.

This story first appeared in a November standalone issue of The Hollywood Reporter magazine. Click here to subscribe.

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