A weeklong road trip through the Santa Ynez Valley wine country drives two middle-aged buddies to unexpected tests of both their varietal and moral palates in “Sideways: The Play.” Adapted by Rex Pickett from his novel (which also spawned the 2004 hit movie), their oenophilial odyssey makes an enjoyable if at times leisurely debut in its stage incarnation at Ruskin Group Theatre.
In the comic misadventures of his narrative stand-in, the perpetually unpublished author Miles (John Colella), Pickett weaves the tribulations of a writing career, the fetishistic elements of wine connoisseurship, and the trauma of failed relationships. In shaping the characters of Miles and his actor friend Jack (Jonathan Bray), Pickett slyly incorporates the personality model of Carl Jung (explicitly cited as one of Miles’ heroes).
Where introspectively analytical and fiercely judgmental Miles keeps the world at a guarded distance, the soon-to-be-married Jack is an extroverted sensualist who dives headlong into experience — even when it means cheating on his fiancée at the earliest opportunity with a lusty tasting room manager (Cloe Kromwell).
In the performance challenge — making this self-absorbed odd couple sufficiently charming to keep us rooting for them — Bray’s Jack is more successful in this regard; his amorous pursuits are clearly the result of libidinous impulse rather than cruel calculation. As Miles, Colella leans heavily on clever dialogue to rationalize willful disregard of his fully functioning moral compass, until shamed into integrity by the waitress (Julia McIlvaine) who represents his somewhat idealized romantic vision.