"School of Scoundrels" has all the components for a mindless, crass, formula-based flick. Only thing missing is any reasonable entertainment value. One can sit through such exercises in borderline idiocy, if the movie has some good cheer, some laugh-out-loud moments, and some good old fashion escapist entertainment. "School of Scoundrels" has all of the above, just not enough of it to justify our time or effort.
Roger (played by John Heder of "Napoleon Dynamite"), is a New York city parking enforcement officer, a regular nice guy, who suffers from the standard issue problems of low self esteem, social ineptitude, and acute reservedness. He is a sort of guy whose book shelf is filled with rows and rows of cheesy self-help books. This is the sort of character that mainstream Hollywood loves these days; this character could have easily been transplanted (to and) from about half-a-dozen recent movies (e.g., "The 40-year-old-virgin").
Roger has a crush on his neighbor Amanda (played by the button-cute Jacinda Barret), which he has difficulty expressing. Also, adding to the complexity is the constant presence of Amanda’s girl friend (Sarah Silverman). (How the movie manages to waste the comic talents of the always funny Silverman is another story). One of his acquaintances, sympathizing with Roger's pathetic state of affairs, offers to help him by referring him to a self help coach ("I know a guy, who does this thing"). When a character in a movie says something cheesy like this, that should mean (in a good stupid movie), "buckle up your seat belts, and get ready for the ride". A good screenplay should have soared from this point, but this movie limps and grovels to take-off, but to no avail.
Roger goes to the self-help crash course conducted by Dr. P (Billy Bob Thornton), and further complications ensue. The movie has some of the best talents working for it. Billy Bob Thornton, the wonderful actor, who consistently creates fully rounded odd-ball characters out of almost any material given to him (e.g., "The Bandits", "Bad Santa"), fizzles out serving an insipid screenplay. John Heder, has made a career out of playing some version of the "every-man-loser" typecast, plays one more such role, reasonably effectively.
The film is directed by Todd Philips who directed the crass, cult classics like "Road Trip" and "Old School". Those movies were funny, this movie is not. Some of the supposedly funny scenes in this movie involve a paint-ball gun and John Heder's groin area, and in another occasion, a defibrillator and Thornton's groin area - this is how inventive the screenplay is. It is not that the movie is out rightly unfunny, it is just insipid, and lingers-on like the taste of a cheap gas-station-coffee. Wise souls will avoid this movie.