The Journey of Sideways


By Rex Pickett

In 1999, I wrote a novel titled Sideways. No one wanted to publish it. A year later, writer/director Alexander Payne (Election, The Descendants) read the unpublished manuscript and optioned my book.

It would be another three years before Alexander got around to directing the film that starred Paul Giamatti, Virginia Madsen, Sandra Oh and Thomas Haden-Church.

Sideways was released in the fall of 2004 and went on to win over 350 critics and awards organizations plaudits. It was nominated for five Academy Awards, winning the Oscar for Best Adapted Screenplay. It swept the Indie Spirit Awards, capturing six, the most ever. The film would go on to gross over half a billion dollars, including DVD and streaming. It never wore out its welcome. It’s safe to say it grew into an enduring cult movie. And it certainly changed the wine world forever.

In 2011, I was approached to adapt my novel into a stage production. Sideways the Play premiered at the Equity-waiver Ruskin Group Theatre in Santa Monica, CA in 2012. Scheduled for a limited engagement of 15 performances, due to ticket demand it was extended multiple times and was staged over 100 times, winning many L.A. theater awards.

Buoyed by that success, my Sideways play “experiment” skyrocketed to the La Jolla Playhouse, a major regional theater that has workshopped many musicals en route to Broadway, with Des McAnuff (Jersey Boys) directing. Tickets sold out so quickly, my play was extended twice before it opened. It ended its run breaking all attendance records for a non-musical at the La Jolla Playhouse in their august 40-year history. To this day, it’s their longest running play ever.

In 2017, I was approached by composer Anthony Leigh Adams who had seen the play and thought it would be great material for a musical. I had never done anything in musical theater, but I was game to try. Working off of the text of my play, and under the creative supervision of Adams, I wrote the Book for the musical, including the lyrics for the 18 songs. I’m quoting myself from an interview about the musical: “The two female lead roles have been greatly expanded and the result is a more lushly romantic piece without sacrificing the bawdy comedy of the original movie that the Sideways fans know so well.”

Just before the pandemic and the shutdown of Broadway in March of 2020, I partnered with entertainment manager John Campbell and he took on the role as lead producer. Working indefatigably under daunting conditions with the spread of Covid, and with only six songs recorded, Campbell forged ahead and found the funding for Adams to finish all 18 of the songs featureed in the musical. As restrictions started to lift, but with theater still not open, John Campbell had a brainstorm: if theaters aren’t fully opening up yet, what about a concert of songs from Sideways the Musical? Excitement ran riot. Especially in Napa/Sonoma, which is so vino-centric, where a property like Sideways is so ubiquitously recognizable.

The Concert of Songs from Sideways the Musical will feature the majority of the songs from the musical, including the rousing opening number ‘God of The Grape’, Maya’s soaringly opening solo ‘The Life of Wine’, the beautiful duet between Miles and Maya ‘Drink a Memory’ and the comic surprise of the evening ‘No Matter How Low We Go’. The master of ceremonies and the host of the show will be myself. I plan to take the patrons through the trajectory of the musical, narrating the story of how Sideways came into being and the incredible journey that I have been on with his creation, in all the various mediums, including now, of course, what I consider to be its apotheosis: the live theatrical musical.

Staged at beautiful Buena Vista Winery, one of the oldest winery properties in Sonoma, three concerts will be staged on Sept. 10, 11, and 12. This magical, sublime venue will be overflowing with wine and good times, but more important: this will be the first time that any of these songs have been performed live. Headed up by a six-performer ensemble, consider it a teaser premiere of the musical as it carves a path through wine country and on to a regional theater and the hoped-for lights of a true Broadway run.

In 1999, a struggling writer wrote a book that nobody wanted to publish. More than two decades later, through a novel, a movie, a play, and now a musical, the indelible characters of Miles and Jack have clearly stood the test of time. They are etched in popular culture in a way that’s impossible to quantify. The musical raises the emotional stakes of their now iconic journey through the then little-known wine region of the Santa Ynez Valley.

American Express and WineDirect proudly sponsor this new artistic iteration of the Sideways story. Come join us for a sweeping musical afternoon of comedy, heartbreak, and romance, all in one glorious performance. Drink a great glass (or three) of Pinot and just remember: “No F***ing Merlot!”

See you in wine country,

Rex Pickett

Rex Pickett Representation:


Manager: John Campbell


Agency for The Performing Arts

TV/Film: David Saunders (310.888.4200)

Theater: Beth Blickers (212.205.4320)