"If you want to be free ..."
A film that refers to Harold and Maude more than once through its signature Cat Stevens' lyric "If you want to sing out, sing out/And if you want to be free, be free" is going to win my heart no matter how unspectacular its screenplay or derivative its plot. The similarities to Rushmore and Ferris Buhler with a bit of Risky Business don't hurt although it is not witty enough to be remembered as those three are.
The titular 18 year old Charlie Bartlett becomes de facto counselor to his public high school mates after the privileged iconoclast has been kicked out of the available private schools.
Cat Stevens fits because Charlie and his troubled teens are trying to figure out where they fit in the scheme of life, always hoping for the elusive freedom; Charlie happens to have the wit and resources to help them better than the equally lost adults. Of that latter group, Robert Downey, Jr.'s principal Gardner has failed since he gave up his successful post as history teacher.
Charlie's mom is a well-meaning, doting, and mildly clueless sweetheart, much more attractive and loving than Harold's rich but distant mother. Both boys and mothers are in the clich?d spot of being without dads and husbands, allowing them to screw up in eccentric ways and retreat to their mansions.
The film has some serious takes on teen obsessions such as their aversion to being spied on (principal has installed video cams) and filming themselves as in YouTube type uploading. The relationship between parents and children is also sobering since unlike in Juno, no facile settling down occurs for anyone, with the exception of the stock teen "fits-in" ending.
So everyone has to figure out a role and play it right. While the film does see characters through to their destinies, the script has few sparkling words of inspiration for the appreciative teen audience. Maybe that's the message itself: If you want to be free, you have to earn it yourself.