Trivia

(at around 1h 5 mins) Ben Affleck and Matt Damon mention that one reason to do a film is because they owe the director a favor. It was writer and director Kevin Smith who brought the script of Will Hunting (1997) to the attention of producer Harvey Weinstein at Miramax.

Baby Silent Bob was played by Harley Quinn Smith, daughter of Kevin Smith.

The voice of Scooby-Doo was provided by Mark Hamill.

Heather Graham was originally offered Shannon Elizabeth's role, but she turned it down because she couldn't figure out why her character would fall in love with Jay.

Because Ben Affleck reprised his role as Holden from Méprise multiple (1997), Kevin Smith had originally wanted to cast different actors to play Affleck and Matt Damon in the Will Hunting (1997) spoof. Smith first considered casting Vince Vaughn and Jon Favreau, then Shawn Wayans and Marlon Wayans, before finally deciding to cast Affleck and Damon as themselves.

Bob Schreck: (at around 1h 5 mins) as an assistant to Gus Van Sant on the set of Good Will Hunting II: Hunting Season. Schreck worked with Kevin Smith as editor on Kevin's Green Arrow run, and as co-publisher of his Clerks and Jay and Silent Bob comics at Oni Press.

Kevin Smith: [37] When the jewel thieves talk about their heist, they have a banner that it's their thirty-seventh heist. The scene of "Bluntman and Chronic", in which Jay and Bob end up, is introduced as "Scene 37, take 1". Justice's prison number is 373737.

Kevin Smith: [comic books] Names of the security guards at Miramax are all references to comic book characters, including Gordon (James Gordon, Gotham City Police Commissioner), Shaw (Sebastian and Shinobi Shaw, members of the Hellfire club), and Akins (another Gotham City Commissioner).

Kevin Smith: [hockey] Randal is wearing a replica Russian hockey jersey. In every View Askewniverse film, there is at least one hockey reference, or someone is wearing a hockey jersey.

Kevin Smith: [off-screen grab] (at around 1h 7 mins) Instead of an off-screen grab, during the scene where they are filming the Good Will Hunting II: Hunting Season spoof, Jay and Silent Bob walk off-screen, and are then pushed back on.

Kevin Smith: [Star Wars] (at around 1h 3 mins) When the Miramax guard catches Jay and Silent Bob, he communicates with base, calling "Echo Base". Echo Base is what the rebel base was called in L'Empire contre-attaque (1980).