"The School of Rock" (2003)
Taking the teacher/classroom genre and injecting it with the combined genius of director Richard Linklater, writer Mike White and star Jack Black, "The School of Rock" is a surprisingly family friendly joy. It gives Black one of his very best roles in Dewey Finn, a washed up rock singer and guitarist who disguises himself as a substitute teacher at a fancy prep school.  Finn puts together a band with his students in hopes of winning Battle of the Bands (so that Finn can pay his rent), and some charming chaos ensues.  Oddly endearing and consistently hilarious, the film is definitely worth a rewatch nearly a decade after its debut. [Peter Knegt]

"Strangers With Candy" (2005)
In the gut-busting film adaptation of the hit TV series "Strangers with Candy," comedian Amy Sedaris (sister to droll author David Sedaris) plays Jerri Blank, a heinous (albeit lovable) 46-year-old former high school dropout who is forced to re-enroll to get her life back on track, after getting released from a rough stint in prison. A self-described "junkie whore" with a nasty overbite and a thing for underage ladies, Blank doesn't have the easiest time fitting in with the popular kids. Even her closeted teacher Chuck Noblet (co-writer Stephen Colbert) gives her a hard time. Folks familiar with motivational speaker Florence "Florrie" Fischer's infamous public-service film "The Trip Back" -- in which she recalls her days as a New York prostitute to a group of bewildered high-school students -- will no doubt get the jokes. After all, it served as the basis for the creation of Blank. [Nigel M. Smith]