With director Peter Segal
  1. The movie was originally titled "Billy the Third: A Midwestern," but it was changed when they found out about the upcoming Adam Sandler movie "Billy Madison." It was also almost called "Fat Chance" until Lorne Michaels suggested "Tommy Boy."
  2. The original script focused on Tommy and the relationship with his new brother-in-law, played by Rob Lowe (which actually sounds a lot like Step Brothers).
  3. The writers of Shrek say they based the relationship of Shrek and Donkey on Chris Farley and David Spade in Tommy Boy.
  4. The idea for the half-dead deer to wake up in their car came from an actual 911 call from a man who was being bit by a deer and a dog at the same time.
  5. A professional wrangler trained a deer for one month to actually destroy that classic car.
  6. Roseanne was slated to have a cameo as a waitress, but timing didn't work out.