Sideways: The Play

Ben Miles Reviews - Theater
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Rex Pickett’s novel, Sideways, was published in 2004. In that same year, and with the same title, it was made into a feature film. The movie went on to win an Academy Award for Best Adapted Screenplay (though only director Alexander Payne and Jim Taylor are credited as screenwriters, not Pickett).

Now author Pickett has transformed his novel into a live staging, and under the inventive direction of Amelia Mulkey Sideways: The Play has found new life in its world premiere at Santa Monica’s Ruskin Theatre Company, through July 22. Like the novel and the film, Sideways: The Play has as its central characters two forty-something bachelors, supercilious Miles (a spot-on John Colella) and carefree Jack (a rakish Jonathan Bray).

Jack is scheduled to be married, and Miles is slated to be his good buddy’s best man. But before the nuptials are to be held, Miles – a wine connoisseur and would-be writer (with a book on the brink of publication) – and Jack – an actor and postmodern philistine – take off to tour the California wine country while having a two-man bachelor party and road-trip.

Jack has but one goal for himself and Miles on this sojourn: to attain physical intimacy with a woman who’s yet to be met; or, in Miles’ case, it’s reconnection with a lady named Maya (a naturalistic Julia McIlvaine), with whom he’s already acquainted and who works as a waitress at Miles’ favorite eatery and watering-hole, The Hitching Post.

When Maya sets up a double date with herself and her girlfriend, Terra (a spirited Cloe Kromwell), a fellow wine aficionado, Jack turns on the charm and hormones only to find Terra head-over-heels smitten with the self-serving womanizer. After several bouts of “intimacy” between Jack and Terra, Jack remains cluelessly dishonest with the vivacious Terra.

Meanwhile, the lugubrious Miles eventually becomes “intimate” with Maya. Yet when Maya reveals just how taken Terra is with Jack, Miles feels the need to confess that Jack is slated to be married in a matter of days with him, Miles, as the groom’s best man. Of course, this information changes the scenario and taints the relationships considerably.

Whether it’s called an off-the-wall conceit or an insightful slice-of-life, Sideways: The Play, like the novel and the film, is a credible tale that plays as if it were a true story. There are no heroes here, only people who want what they want and will pretty much do anything to provide for their purported needs. These characters are not noble but they appear to be real.

With sterling production values (sets by CJ Strawn and costumes by Lola Kelly) and a delightful ensemble (Kristelle Monterrosa, Hamilton Matthews, Paul Denk, and Carl Kocis) who make for quick and comedic scene-changes, Sideways: The Play is similar in theme and spirit to the movie, but, as playwright and novelist Pickett indicated in a brief pre-play conversation (on opening weekend Pickett was, appropriately enough, pouring pinot noir for audience members before the two and a half-hour show began), the play is really the novel set to stage.

SIDEWAYS: THE PLAY continues at the Ruskin Theatre Company – 3000 Airport Avenue, Santa Monica – through July 22. Evening performances are Fridays and Saturdays at 8 p.m. Sunday matinees are at 2 p.m. For reservations, dial (310) 397-3244.