Wine Enthusiast Podcast · Wine Enthusiast Magazine

Episode 163: Rex Pickett and the Making of Sideways 20 Years Later

·1 hr 11 min·5 clips

Rex Pickett's credit card was declined for $6 just as Alexander Payne wanted to option Sideways.

This episode features author Rex Pickett discussing the creation and legacy of his novel "Sideways" with host John Capone, executive editor of Wine Enthusiast Magazine. Pickett wrote the novel that became the acclaimed 2004 film directed by Alexander Payne. The conversation marks the 20th anniversary of the movie's release. Pickett was an unpublished author living in a rent-controlled Santa Monica apartment when he wrote the initial short story. His completed manuscript was rejected by every publisher who read it. The unpublished work eventually reached director Alexander Payne's desk. Pickett learned Payne wanted to option "Sideways" via a message on his answering machine. At that same time, Pickett had his credit card declined for a six-dollar charge at Baja Fresh. The film deal did not immediately transform Pickett's financial situation. It did, however, provide him two decades of travel within the global wine community. The success also secured his role in the creation of a cinematic classic. The film's impact famously generated significant animosity from Merlot producers. Pickett's character, Miles Raymond, was portrayed by actor Paul Giamatti. The episode's tone is conversational and reflective, focusing on personal history and cultural impact. The style is anecdotal, driven by Pickett's firsthand storytelling. Wine lovers and film enthusiasts, particularly fans of the movie "Sideways," would deeply enjoy this behind-the-scenes account. Listeners seeking technical wine analysis or current industry news might find the episode less aligned with their interests.

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