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CT PRESENTS SIDEWAYS

  • Jun 4, 2024
  • 3 min read

Comic romp through wine country up next at CT


The Cumberland Theatre will continue their 36th Season with the comedy-drama Sideways based on the popular 2004 film. The show will run June 6th – 23rd for a total of ten performances. The show is being sponsored by Perineologic.


Written by Rex Pickett, who also penned the best-selling novel of the same name – which has spawned three sequels, the show centers around unpublished writer Miles Raymond s and his friend Jack Manse who are embarking on a wine-tasting road trip to salute the final days of Jack’s bachelorhood. The trip 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. Miles wants to spend the week relaxing, playing golf, and enjoying good food and wine. However, much to Miles' annoyance, Jack wants to have one last sexual fling before getting married. Emerging from a haze of Pinot Noir, wistful yearnings, and trepidation about the future, the two inevitably collide with reality.


The film version starred Paul Giamatti, Thomas Haden Church and Virginia Madsen. The film drew attention and increased tourism to the Santa Ynez Valley wine-growing region in Santa Barbara County and California's Central Coast. During the film, Miles speaks fondly of the red wine varietal pinot noir while denigrating merlot.[2][3] After the film's U.S. release in October 2004, merlot sales dropped 2% while pinot noir sales increased 16% in the United States.


The CT rendition of Sideways stars Bill Dennison as Miles and Seth Thompson as Jack. Dennison was last seen as Chris/Inspector Carter in The Play That Goes Wrong. Thompson was last seen as Alvaro in The Rose Tattoo. Also appearing as Maya and Terra – the women who cross their path – will be Jenn Levi and Kimberli Rowley. Levi currently resides in Orlando, Florida where she as appeared both on stage and on film. Rowley is the current Artistic Director of CT and was last seen onstage as Serafina in The Rose Tattoo.


The supporting cast, who play a large variety of diverse characters, are Erik Alexis, Michaela Hale, Grace LaCount, Savannah Tagliaferro and Mark Worth.


The show is being directed by Wendy Walker. The design team consists of Anthony Tagliaferro (set design), Walker (costume design), Trevor McCabe (props design), Reed Simiele (lighting design), Brendon McCabe (sound design), Brian Records (fight director) and Marty Jellison (projection design). The run crew is comprised of Katie Zimmerman (stage manager), Thompson (fight captain), LaCount (wardrobe assistant) and Jaiden Courrier (assistant stage manager).


A preview performance will be held Thursday, June 6th at 8:00 pm. Following the preview, performances are June 7th – 19th with Friday and Saturday performances at 8:00 pm and Sundays at 2:00 pm. An opening reception is included in the ticket price for Friday, June 7th.


VIP Bar Seating is also available, which includes bar seating up front with complimentary wine flight and snacks as well as additional tastings served during the show.

More information on ratings, group sale, etc. can be found on cumberlandtheatre.com where single tickets are available for purchase as well as 2024 Season Passes. Reservations can also be made by calling the box office at 301.759.4990.

Please note, the show contains strong language, some violence and sexual situations. It is not intended for younger audiences.

 
 
 

29 Comments


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lili xie
Apr 27

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I’m excited about this production of Sideways and can’t wait to see how Cumberland Theatre brings it to life! geometry dash subzero

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meery232er
Dec 31, 2025

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