Co-writer and director Todd Phillips was having a hard time finding a blueish 1976 Lincoln for Huggy Bear. When he revealed this to Snoop Dogg, he was surprised to learn that Snoop actually owned a car of the right color, and it's his car that appeared in the movie.
Ben Stiller went to stunt driving school and did well, but he still wasn't approved to do all of his driving stunts.
When Vince Vaughn slapped Snoop Dogg during the golfing scene, it was unexpected the first time. Todd Phillips said, "Snoop went on with the scene, and then when it ended he said, 'What the hell was that?'"
Originally, co-writer and director Todd Phillips wanted the knife-throwing scene to feature ninja stars instead. But the idea was scrapped when learning that any scene featuring ninja stars would automatically get an 18 Rating in the UK.
When filming the yacht scenes with Vince Vaughn, Todd Phillips became very seasick and mentioned that he hated boats. When asked why he included one in his screenplay, he vowed never to write or shoot a scene on boats again.