Masterminds

Oswald 'Ozzy' Paxton (Vincent Kartheiser) is a Playful Hacker who is forced to take his stepsister Melissa (Katie Stewart) to her prep school, Shady Glen (where he was kicked out after a prank), after being busted by his parents for downloading an illegal copy of the game Scream II (no relation to the film). Before leaving, Ozzy decides to pull one last prank...until he sees men armed with guns arriving on the scene.

Turns out Rafe Bentley (Patrick Stewart -- yes, that Patrick Stewart), Shady Glen's new head of security, has hatched a plan to hold the children of Shady Glen as ransom to extort money from their wealthy parents. So now Ozzy has to use his hacker skills to save the day.

This film contains examples of:

 * Absurdly Spacious Sewer: Bently has a bunch of AT Vs tricked out wit rocket launchers waiting in the sewer tunnels as an escape route
 * Affably Evil: Bentley
 * Bald of Evil: Bentley, again.
 * Badass Teacher: Claire Maloney, the headmistress of Shady Glen.
 * Big No:
 * The Cracker: Ozzy is introduced as this at the beginning, downloading a game before it goes on the market to sell illegal copies.
 * Die Hard On an X
 * Evil Brit: Bentley
 * Hey It's That Guy:
 * Everyone will recognize Captain Picard as Bentley, and Connor as Ozzy.
 * Isn't that the pigeon lady from Home Alone 2 as the headmistress of Shady Glen?
 * Katie Stewart would later play Kitty Pryde in X-men 2, alongside Patrick Stewart. They are not related, btw.
 * Hollywood Hacking: Computer hacking consists of playing a literal computer game, consisting of hunting for a "valid entrance" in a 3-D animated dungeon (with hostile skeletons!), while the system itself proclaims full awareness of your activities and their illegality. It's a good enough sport to let you proceed without a fuss if you win
 * Hot Mom: Yep, Ozzy's stepmom is quite a looker.
 * I Have Your Sister
 * Large Ham: "UNITED! UNITED!"
 * Keep Circulating the Tapes: Literally, as the film has only been released on VHS.
 * The Mole: Rafe, head of security at the school.
 * Noodle Incident
 * Mooks
 * Playful Hacker
 * Unlikely Hero
 * X Meets Y