Sideways/Trivia

• Actor Allusion:
  • Thomas Haden Church's character is a former TV star now doing commercial voiceovers, which mirrors Church's own career.
  • The pictures of Miles and his father are actual pictures of Paul Giamatti with his late father, Major League Baseball Commissioner Bart Giamatti.
• Hey, It's That Guy!: The four main cast members have a litany of supporting roles on their resumes. Virginia is also known as the sister of a certain other Madsen.
  • Also invoked in-universe. A waitress recognizes Jack from his stint on Days of Our Lives, which he parlays into sleeping with her.
  • Shares the same universe as Election, since both films were directed and partially written by the same person. Look for the principal from the high school from Election at the country club, who even appears in the credits as "Vacationing Dr. Walt Hendricks".

(Jack and Miles are talking about Maya while walking by a golfer and his son)
Jack: Don't you just want to feel that cozy little box grip down on your johnson?
Vactioning Dr. Walt Hendricks: Hey, you mind keeping it down, buddy?

• Romance on the Set: Sandra Oh was married to director Alexander Payne. They divorced shortly after.
• Star-Making Role: Paul Giamatti, from character actor 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.
• 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.