- Bill Murray was attached to play Dr. P at one time with Christopher Masterson playing Roger. Both had to pull out of the project at the last minute.
- Director Todd Phillips first offered the lead role to Howard Stern (Phillips is a big Stern fan), but Stern had to turn it down because he was about to leave terrestrial radio for satellite radio and did not have the time to film a movie. The role eventually went to Billy Bob Thornton.
- Ben Stiller's cameo was shot in 2 days in California because he was not able to fly to New York for filming due to a scheduling conflict.
- Diego (Horatio Sanz) says, "Things are going to change, I can feel it." quoting Beck's song, "Loser".
>>> WARNING: Here Be Spoilers <<<
Trivia items below here contain information that may give away important plot points. You may not want to read any further if you've not already seen this title.
- SPOILER: Dr. P's rules "From the Bar to your Bed" are:
- Be dangerous, it's cool
- No compliments, *ever*
- Always get the girl alone
- Wherever you are, the place is lame!
- Relate to her
- Lie, lie, and lie some more
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