- Career Resurrection: For Virginia Madsen, an '80s sex symbol who had been relegated over the years as simply "Michael Madsen's sister".
- Creator Backlash: While he liked the movie overall, Sideways author Rex Pickett did not approve of the changes actress Sandra Oh made to her character:"She changed the name of the character to Stephanie. She changed her vehicle to a motorcycle. She added the mixed-race kid. I hate that bowling alley scene in the movie. I leave every time I see it. [Director] Alexander [Payne] had just married Sandra Oh. He was in love with her. Alexander would never have taken those suggestions from anybody else. Then they had a bitter divorce, and she got half the money he made from Sideways, which was a lot of money because Alexander got points from the gross worldwide. But when she got the role on Greys Anatomy, that was afterward and she didnt have to share that money."
- Defictionalization: The movie drove so much tourism to Buellton, CA in the years since its release that the city's signature Windmill Inn, where Miles and Jack stay during their trip, was renamed "Sideways Inn" during a renovation in 2016.
- Real-Life Relative: The pictures of Miles and his father are actual pictures of Paul Giamatti with his late father, Major League Baseball Commissioner Bart Giamatti.
- The Red Stapler: Interest in wine and tours shot up like crazy after the film came out; it even affected the sales of certain wines. Miles's love of Pinot Noir caused that wine's sales to soar, while his disparaging of Merlot ("If anyone orders Merlot, I'm leaving; I am NOT drinking any FUCKING Merlot!") caused Merlot's sales to dip, although it continues to be the most prevalent wine in the States.
- Also crosses with Aluminum Christmas Trees. Miles' rant about Merlot was not just out of personal preference: In the years leading up to the film's release, there were a lot of subpar Merlots being bottled, and the consensus among wine reviewers is that the drop in sales and production after the film's release led to a great increase in quality. Conversely, the increased demand for Pinot Noir has led to no little debate over the quality of what's been produced.
- Romance on the Set: Sandra Oh was married to director Alexander Payne. They divorced shortly after.
- Sleeper Hit: Fox's biggest indie hit ever at the time, scoring $70 million domestically after an initial limited release turned into an eventual wide release.
- Star-Making Role:
- Paul Giamatti, from character actor (as seen in films like The Negotiator and The Truman Show) to now having the clout for billing on movies. At the time, his best known role was as the antagonist of Big Fat Liar.
- For Thomas Haden Church, it was more of a Career Resurrection. He was a star on the '90s sitcom Wings, but faded into obscurity until this role brought him back to the spotlight. Church nabbed the role as The Sandman in Spider-Man 3 based off his performance here.
- Sandra Oh landed one of the lead roles in future smash hit Grey's Anatomy shortly after the film's release.
- Throw It In!: In film reviews, it is suggested that Miles is very self-absorbed in his own intelligence because he does the New York Times crossword in pen (while driving!). This was not intentional; the crew simply gave Paul Giamatti a pen because that was all they had on hand, but it indeed works for the character nonetheless.
- Wag the Director: According to the book's author, Rex Pickett, all the changes from his novel regarding Stephanie's character came from Sandra Oh to the writer/director, her then-husband Alexander Payne.
Trivia / Sideways