According to Steve Zahn on Couch Surfing (2018), the "COME ON AH YEEEEEEEH-HA!" line was from the middle of a Neil Diamond performance. Neil asked about that line, and they replied they were saying his words. Neil didn't believe this and they had him listen to the part of his performance and he realized he did say that.
The magician in the bar hitting on Judith is Kyle Gass, lead guitarist and co-writer in Tenacious D (1997) with Jack Black.
The Coach's motto to his students, "If you can dream it, you can do it" is actually a quote originally said by Walt Disney.
R. Lee Ermey was cast as the coach because director Dennis Dugan originally wanted to approach him about playing Chubbs in Happy Gilmore (1996). However the star and co-writer of that movie Adam Sandler, preferred Carl Weathers for the part and Dugan eventually agreed to casting Weathers and ultimately dropped Ermey. Although he was pleased with Weathers' performance in the end, Dugan still felt bad about letting Ermey go and promised to offer him a role in a future film which ended up being this movie.
In the theatrical trailer a pair of blue briefs were digitally painted onto Steve Zahn in one scene because the MPAA said the scene was too revealing for general audiences.