- The Cast Showoff: Will Ferrell did his own singing and John C. Reilly did his own drumming. An interesting aversion is that Reilly, who is known to be a very talented singer as well, doesn't.
- Creator's Oddball: Compared to Adam McKay's other work with Will Ferrell, in spite of its silly premise, Step Brothers is more of a grounded comedy-drama that explores the more realistic consequences of Dale and Brennan's Manchild antics.
- Defictionalization: Inspired by the film, the Catalina Wine Mixer was first held in 2015 and had its third annual event in late 2017.
- Enforced Method Acting: According to John C. Reilly, his farting was geniune. He says he was influenced by a legend about John Malkovich doing a play that called for him to pee on stage, which he reportedly did every night.
- Mid-Development Genre Shift: At one point, Adam McKay considered making the film an actual drama.
- Stillborn Franchise: Will Ferrell and John C. Reilly have talked about a sequel. Reilly had the idea. According to Adam McKay, the characters would be mature and have jobs. "One of them's married and has a kid. They're still kind of goofballs but they've taken three or four steps. Then we have an idea for something happens that knocks him back to square one, and one of the brothers, John C. Reilly sort of instigates it, like 'we can't take this anymore.' And things go really bad, their lives kind of fall apart. They have to pull it back together is sort of the basic structure." McKay has also said that ideas that were not used in the first film may be used in the sequel.
- What Could Have Been:
- Jon Hamm auditioned for the role of Derek.
- Lesley Ann Warren was offered the role of Nancy, but had to turn it down due to scheduling conflicts with In Plain Sight.
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