Sideways

by  Rex Pickett

Full Length Play, Dramatic Comedy  /  3m, 4f

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

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  • Cast Size

    Cast Size

    3m, 4f
  • Duration

    Duration

    120 minutes (2 hours)
  • SubGenre

    Subgenre

    Adaptations (Literature), Adaptations (Stage & Screen)
  • Accolades

    Accolades

    Not Applicable
  • Audience

    Target Audience

    • Adult

Additional Info

A wine-tasting road trip to salute the final days of bachelorhood careens woefully sideways as two friends 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 themselves drowning in wine and women. Emerging from a haze of Pinot Noir, wistful yearnings, and trepidation about the future, the two inevitably collide with reality.

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Reviews

REVIEWS

“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 

Keywords

Aging, Friendship, Love

Considerations

Performing Groups

  • Community Theatre
  • Professional Theatre
  • Blackbox / Second Stage /Fringe Groups

Cautions

  • Caution Alcohol Alcohol
  • Caution Strong Language Strong Language
  • Caution Mild Adult Mild Adult Themes

License details

  • Minimum Fee: $75 per performance

Production

Details

  • Time Period: 1990s
  • Duration: 120 minutes (2 hours)
  • Setting: 1999. Most of the play is set in the Santa Ynez Valley, an hour north of Santa Barbara, CA.
  • Additional Features: Not Applicable
  • Features / Contains: Contemporary Costumes / Street Clothes

Casting

3m, 4f
MILES - 39, introverted, intellectual. 
JACK - 40, ebullient, extroverted.
MAYA - 35, intuitive, deep, soulful. 
TERRA - late 20's/early 30's, coquettish. 
PHYLLIS / CHARLIE / EVELYN
LISSY / ROSIE / VICTORIA 
CHRIS / DARYL / POURER
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Cast Attributes

  • Reduced casting (Doubling Possible)

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Authors

Rex Pickett

Rex Pickett is the critically-acclaimed author of the novel Sideways, upon which the Oscar-winning Alexander Payne film of the same title was adapted. Not only did the film win over 350 awards from major critics and awards organizations and completely change the wine world, the film has continued to garner a worldwide ...

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Sideways premiered at the Ruskin Group Theatre in Santa Monica, CA in May 2012 under the direction of Amelia Mulkey.

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