Chris Farley uses the same football play with the kids at the youth center - "32 belly option" - as he did when he and Rob Lowe went cow-tipping in Tommy Boy (1995).
Fred Wolf, who did punch-up work on Tommy Boy (1995), claimed the studio told him to "deliver a finished script by midnight on Sunday, the last day Chris was contractually allowed to get out of the movie. If I didn't have a finished script, any finished script, they were going to sue me." Wolf wrote 45 pages in a weekend, and dropped the script off at Paramount 15 minutes before his deadline.
The security guards behind Mike at the 'Rock the Vote' scene are Chris Farley's real-life brothers, Kevin P. Farley and John Farley.
The cabin used on the outskirts of town is the same cabin used as Jill's cabin in Joe Dirt, another movie starring David Spade.
"Black Sheep" was a contractual obligation for Chris Farley. He had signed a two picture deal when he made "Tommy Boy", and he now owed them a second movie. Paramount was rushing to get a script out before he was able to get out of the contract. At the same time, Farley was being offered $3 million for the lead role in Sony's The Cable Guy (1996). The original "Cable Guy" script was tonally very different from the finished product, as it was more of a simple fun story. As Farley was about to sign the deal, somehow, the "Cable Guy" script made it to Jim Carrey, and he suddenly expressed interest in doing it. Because Carrey was the more bankable star, Sony let Farley go and went with Carrey instead, who turned it into a dark, black comedy. Sony was going to pay Carrey $20 million, the highest payday for an actor at that time. As for Farley, Paramount had exercised the option clause in his two picture deal with them, forcing him to do this film instead. Sony did pay Farley off for "Cable Guy", but Paramount only paid him under $1 million for this film.