When it comes to terms used to describe or define bad people, "scoundrel" doesn't really carry the same weight of say "evildoer," "miscreant" or "villain," at least not like it once did. In fact, it nearly has something of a light or playful air to it, certainly much more so than its synonym cousin, "rogue."
When I hear the term, I conjure up the comedic villains in the old "Pink Panther" movies, or especially Steve Martin and Michael Caine's characters in the appropriately titled "Dirty Rotten Scoundrels." The filmmakers responsible for "School For Scoundrels" are probably hoping viewers will have the same reaction to their film.
After all, it's about an unscrupulous man who charges a great deal of money to teach losers how to be scoundrels or, to be more exact, brutish womanizers. And to show just how bad he is, he sets his sights on the object of desire of one of his students, the milquetoast's next-door neighbor. Accordingly, that young man has to battle his mentor using the tricks he taught him to win back his girl.
Thus, while it possesses similarities to "DRS" (and the 1964 film, "Bedtime Story" that inspired it), there are enough differences from it, as well as plenty of potential for a no holds barred, cinematic clash featuring dirty tricks designed to undermine each other. And with Billy Bob Thornton as one-half of the combatants (in the bad teacher role), things would seem set for a fun time.
Unfortunately, the film is beset by all sorts of problems. The first is that this isn't a fair fight, or at least a balanced one. Sure, we're supposed to root for the "outclassed" underdog student to best his mentor at his own game. Yet, that character is played by Jon Heder, the actor who shot to stardom in the annoying "Napoleon Dynamite." While not quite as nerdy here, he's pretty much playing the same character type (the supposedly lovable loser).
Accordingly, he wouldn't stand a chance against Bad Santa, uh, Morris "Bad News Bears" Buttermaker, I mean Dr. P., all of which similarly share the same sort of character attributes (mean, nasty, acerbic, et al.). That is, unless the filmmakers - writer/director Todd Phillips ("Old School") and co-writer Scot Armstrong -- concocted imaginative ways for the student to twist what he's been taught back around on his master. Unfortunately, neither the initial lessons (before the betrayal) nor such twisting is particularly clever, let alone funny.
That is, unless you're a diehard fan of Thornton and/or Heder's particular style of playing these sorts of characters. Otherwise, we're "treated" to scenes of the students having to be confrontational at the drop of a hat (actually a beeper), resulting in them interacting with certain people the way they wouldn't normally do so (which could have been funny had more thought been put into the gags). Then there's a long sequence involving a paintball battle including inferences to male rape, "Deliverance" style, that isn't remotely amusing (see either "Jackass" movie if you want to chuckle over people inflicting pain on others - without that decidedly unfunny add-on).
Following the mentor going after the protégé's female target, we then get to see Roger hit his teacher with tennis balls while playing doubles (been there, seen that done better before), the latter making it look like the former is a stalker, a parking ticket, a fake gay love letter and such.
None of it's remotely funny, so the apparently desperate filmmakers then went to the bullpen in hopes of some comedic salvation from none other than Ben Stiller. He plays a former student who was similarly duped and now lives a loner life, save for the stereotypical bevy of cats (all the more to make him look crazy). Alas, even this extended cameo (or the sight of the hulking Michael Clarke Duncan in a blonde wig during a dating simulation) can't do anything to save the film.
Simply put, the battle's never believable (especially in the "Mission: Impossible" type finale), and the chosen weapons and tactics aren't funny, smart, and/or clever enough to get us rooting for one guy or the other, let alone laughing at their antics. In the end, "School for Scoundrels" fails to get even a passing grade and should have been held back a year (or more) in an attempt to improve it. The film rates as a 3 out of 10.