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.
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.
Originally in development at Warner Bros. Pictures (which had a financing deal with Village Roadshow Pictures), but was placed in turnaround in early 2000. Sony Pictures later picked it up.