This is the first film to win best screenplay from all five "major" critic groups (National Board Of Review, New York, Los Angeles, Brodcast and National Society Critics), the Golden Globes, the WGA and, ultimately, the Academy Awards.
During an emotional scene in the film, Miles talks with great passion about Pinot Noir. After the release of this movie, sales of Pinot Noir wines rose by more than 20 percent over the 2004-05 Christmas/New Year period, compared to the same period the previous year. A similar phenomenon was experienced in British wine outlets. Miles is deeply disparaging, in a different scene, about Merlot, and sales dropped after the film came out. Ironically, Miles's prized bottle of wine, a 1961 Château Cheval Blanc, is a blend of Merlot and Cabernet Franc, another grape Miles disparaged.
Most of the wine used in the wine-tasting scenes was non-alcoholic. The actors wound up drinking so much of it that it made them nauseated (and had to periodically switch to the real thing to clean out their palates).
A slapstick scene involving Miles hitting a dog with his car while driving around was cut because it didn't fit the overall mood of the movie and didn't follow animal regulations that Hollywood had on using animals in movies.
Thomas Haden Church' had left film acting, concentrating on voiceover work, when he received a phone call from Alexander Payne to audition for the role of Jack. Church was a finalist for a role in About Schmidt (2002), another Payne film, and Payne wanted to use the actor in one of his films.
Both of the New York Times crossword puzzles that Miles solves in the movie are actual published puzzles. The constructor's byline on the second puzzle Miles solves is visible; the puzzle was constructed by Alan Arbesfeld, and was published in the Times on 9 October 2003. The constructor's byline on the first puzzle (the one Miles solves while driving) is not visible; this puzzle was constructed by Craig Kasper and was published in the Times on 27 September 2003.
During the opening credits, Miles drives west along Sunset Boulevard crossing the 405 freeway, indicating that the Erganians' house is located in the posh L.A. neighborhood of either Brentwood or Pacific Palisades.
According to W. Blake Gray of the San Francisco Chronicle, the producers had originally wanted to use a bottle of Petrus as the treasured wine gathering dust in Miles' apartment. But Christian Moueix, the chateau's owner, read the script and decided to pass. So, instead it was a bottle of 1961 Cheval Blanc.
When Miles hits the ball back at the golfers behind them, the person who actually hit the ball was the author of the novel the film was based on. He claims that Paul Giamatti's exceptionally poor golf form made it impossible for him to accomplish the shot.