This was Joe Roth's first picture as director in 11 years. Initially Billy Crystal was slated to direct the picture. When Roth read the script, he was totally immersed and liked the script so much that he wanted to direct. Crystal granted Roth's request to direct the picture and stayed on as producer.
When Dave enters the hotel bar to speak with Lee, Dave says to the bartender "I'll have whatever he's having." This is an in-joke in reference to the famous "I'll have what she's having" scene in When Harry Met Sally... (1989), which also starred Billy Crystal.
When Hal is talking to the press at the press junket his microphone shorts. As he says the line "...this is the most honest movie I have ever made" after the word "made" you hear a click and can see the flash in the microphone headpiece as it shorts.
One the first pass by the MPAA, the film was rated R for it's adult language and sexual innuendo. Revolution Studios and Columbia Pictures made the small cuts necessary to get the desired PG-13 rating.