Longtime best friends Miles and Jack set off on “the ultimate road trip, the last hurrah” in Rex Pickett’s Sideways The Play, now getting a terrific World Premiere staging by Santa Monica’s The Ruskin Group Theatre Co.

 If the title Sideways rings a bell, it’s probably because of Alexander Payne’s Academy Award-winning big-screen filming of Pickett’s novel of the same name, with Paul Giamatti and Oscar-nominated Thomas Hayden Church as a pair of besties road-tripping it up to the Santa Inez wine country for a week-long adventure, that “last hurrah” before Jack’s rapidly approaching wedding just seven days away.

It takes considerable chutzpah to undertake a brand-new adaptation of a novel whose much-lauded film script won Payne and Jim Taylor the Oscar (and a host of other awards), and even more cojones to transfer a sweeping, multi-locale coming-of-middle-age journey to as intimate a space as the Ruskin stage—but wonder of wonders, Pickett and company have pulled it off, thanks to a snappy script, inspired direction by Amelia Mulkey, a superb team of actors, and an imaginative, splendidly rendered design package. That each ticket comes with complimentary Pinot Noir which can be sampled before and during the performance as well as at intermission is an added bonus, making this package deal as irresistible as they come.

 Pickett’s stage adaptation has been said to hew closer to his novel than Payne’s film (e.g., the movie’s Stephanie is once again a daughterless Terra and a hilarious boar-hunting sequence not seen on screen has been restored), yet it could just as easily be a screenplay, its rapid succession of scenes and locales being about as cinematic as they get. In fact, in less skilled hands than Mulkey’s, set designer CJ Strawn’s, and “ensemble choreographer” Kristelle Monterrosa’s, Sideways The Play could easily get bogged down in scene change upon scene change. As staged at the Ruskin, however, even those scene changes are attention getters.

Sideways The Novel, The Film, and The Play each center on wine aficionado Miles (John Colella at the Ruskin), wallowing these past two years in wine-soaked post-divorce depression as he awaits word on the publication of an ambitious novel we can’t help sensing may never see the light of Barnes & Noble. Since Miles’s longtime best friend, actor-turned-director Jack (Jonathan Bray), can’t bear the thought of tying the marital knot without one last wild-and-crazy night of sexual debauchery, who better to join him than Miles, for whom a bit of “nut-busting” may be just what the doctor ordered to get him out of his two-year funk.

 Once arrived in wine country, the 40ish buddies run into a pair of younger beauties, recently-divorced sommelier-in-training Maya (Julia McIlvaine) and sexy Italian-American waitress Terra (Cloe Kromwell). Though it takes a while for Miles and Maya to connect, Jack and Terra hit it off from the get-go, their hot-and-heavy screams and moans providing a hilarious backdrop to the other couple’s getting-to-know-you chitchat in an adjoining room. (The scene, funny in the movie, is even funnier on stage.)

As Miles becomes more and more uncomfortable with his best friend’s premarital shenanigans, not only Jack’s impending nuptials but the future of the best buddies’ friendship gets put into jeopardy, with audiences kept in suspense up to the play’s final moments.

 At over two-and-a-half hours, Sideways The Play could probably use a bit of trimming, but other than that, Pickett’s script is a winner, and a perceptive commentary on the age-old “Men Are From Mars, Women Are From Venus” conundrum that not only doesn’t let “Martians” off easily but gives “Venusians” their chance to strike back, both figuratively and literally.

As Miles and Jack, Colella and Bray have the tough assignments of not only being onstage virtually throughout a dialog-heavy play but of erasing memories of their screen predecessors, challenges at which both actors succeed with flying colors. Neither Miles nor Jack is a saint, yet Colella and Bray manage to keep us rooting for a self-pitying drunk and a philandering louse, making them human and vulnerable and amusing to boot. The spontaneity and fire each actor brings to his role prove textbook examples of intimate stage acting at its best, making a ticket purchase well worth the cost for would-be thespians in search of a master class.

 McIlvaine and Kromwell provide splendid support. It’s both fun and rewarding to see the coolly beautiful blonde Maya finally turn tigress, just as it is to see Italian spitfire Terra reveal her vulnerable side once the reasons for Miles’s and Jack’s road trip come to light, as inevitably they must.

Hamilton Matthews (Jack), Monterrosa (Libby), Carl Kocis (Charlie) and Paul Denk (Chris) make up the abovementioned Sideways ensemble, whose scene-change choreography by Monterrosa not only eliminates any need for light-dimming as furniture and props are moved on and off stage ever so inventively but makes each scene change an entertaining treat. Matthews’ quirky boar-hunter and Kocis’ and Denk’s witty wine servers are deserving of kudos as well.

 Strawn’s set design is a wonder of ingenuity, as it converts from a series of winery bars to the front seat of Miles’s car to a Santa Inez Valley forest to the two buddies’ twin-bedded hotel room. (A “montage” sequence in which Miles and Jack get more and more inebriated as they travel from vineyard to vineyard is particularly inspired.) Lola Kelly’s costumes are carefully chosen ensembles designed to reflect each character’s personal choices. Sideways’ uncredited lighting design is thoroughly first-rate as is the production’s jazz-tinged uncredited sound design. Fight choreographers Dan Speaker and Jan Bryant have staged some exciting, realistic-looking fisticuffs.

Nicole Millar is assistant director, Jeff Faeth design assistant, and Cliff Wagner master builder. Elizabeth Bortnem is stage manager.

John Ruskin, Mikey Myers, Sheri Levy, Grace Shen, Linda Sullivan, Kevin Wyrauch, Christine & Jordan Kaplan, and Aubrey & Amelia Anderson are executive producers. Jason Matthews, Mike Reilly, and Eddie Jauregui are producers. Sara Delpizzo is associate producer.

Given Sideways The Movie’s multiple award wins (imdb sets the grand total at 106) along with its big bucks box office and hit DVD status, interest in Rex Pickett’s Sideways The Play is likely to be high indeed. With Pickett and company more than meeting the challenges involved in adapting a novel-turned-film into a two-act play, you can expect all 65 Ruskin Group Theatre Co. seats to be filled throughout Sideways’ scheduled 2-month run if not beyond. Wherever you live, a road trip to the Ruskin is well worth taking.

Ruskin Group Theatre, 3000 Airport Avenue, Santa Monica.

–Steven Stanley
May 25, 2012
Photos: Agnes Magyari

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