About the Play:

Sideways is a full-length dramatic comedy adapted for the stage by Rex Pickett from his own novel. The story of two best friends – wine snob Miles and his minor-league Hollywood actor friend Jack – drinking their way through California's wine country, on one last blowout trip before Jack gets married. Miles and Jack must face their uncertain futures…just as soon as they figure out how to survive their chaotic present.

Sideways is a wine-tasting road trip through the vineyards of California's Central Valley to salute the final days of bachelorhood. It careens woefully sideways as two longtime best friends – just-divorced Miles and soon-to-be-married Jack – 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 out that there's more to be savoured in California than a few new bottles. For when they meet the equally strong and complex Maya and Terra, the foursome learns just how intoxicating a good glass of wine and good company can be, for better and for worse. Emerging from a haze of Pinot Noir, wistful yearnings, and trepidation about the future, Miles and Jack inevitably collide with reality. Previously adapted as a major motion picture, Sideways garnered numerous nominations and awards, including an Academy Award win, two Golden Globe Awards, four NY Film Critics Circle Awards, a SAG Award, six IFP Independent Spirit Awards, and is one of the National Board of Review of Motion Pictures Top Ten Films of 2004.

Sideways premiered in 2012 at the Ruskin Group Theatre in Santa Monica, California and ran for six months. It moved to the La Jolla Playhouse in 2013, enjoyed an extended run, and then toured. The European premiere was in 2016 at the St James Theatre in the West End of London. The play has been performed in regional, college, and community theatre productions.

Cast: 4 female, 3 male (doubling possible)

What people say:

"A sublime variation on the buddy road movie, infusing the midlife crises of the two main protagonists with hope and poetry." — New York Post

"Hysterically funny yet melancholy comedy." — Hollywood Reporter

"More involvingly intimate than the movie." — LA Weekly

"Every word is pure prose poetry ... should be high on your list of plays to see." — Santa Monica Mirror

About the Playwright:

Rex Pickett is a California based American novelist and filmmaker best known as the author of the original novel and the stage version Sideways, which was adapted into the most successful wine movie of all time. The Alexander Payne film of the same title garnered numerous nominations and awards, including an Academy Award win, two Golden Globe Awards, four NY Film Critics Circle Awards, a SAG Award, six IFP Independent Spirit Awards, and is one of the National Board of Review of Motion Pictures Top Ten Films of 2004.