Me and all of my cousins were introduced to the original BBC series The Hitchhiker’s Guide to the Galaxy at about that age, and all of us, male and female, were hooked. You can check it out Here
2 movies, which went on to become cult classics, from my formative years in the late 70’s are I Want to Hold Your Hand and 1941. These 2 movies are quite different than most Steven Spielberg productions. Several of the actors appear in both movies and they are quite memorable, especially Wendy Jo Sperber and Eddie Deezen who play some of the funniest characters I’ve ever seen in movies. There is also a scene in 1941, featuring Slim Pickens, who has been taken captive on a Japanese submarine, that will make you “poop your pants” with hilarity. Both movies are very intelligent and extremely funny. A mature 14 year old will not only appreciate the humor, they’ll feel quite superior for having the intellect to really understand them. You can read more about them Here and Here
Of couse, don’t forget about Monty Python’s Flying Circus TV show, or the movie (which has multitudes of funny quotable quotes) Monty Python and The Holy Grail. My brother was 16 when he and his friends (all the super smart kids at school) first watched this movie, and they went around quoting it. I knew all of the quotes before I saw the movie. Enjoy this clip of The Knights sho say Nee
One of my favorite movies, also from that same time period (forgive me if I’m dating myself, but some great stuff came out in the late 70’s and early 80’s) was Young Sherlock Holmes I’m a Sherlock Holmes junkie and I thought this was a really great “imagined” story of how the detective came to be who he became in his later years. I had forgotten that this movie is also a Steven Spielberg production, so there is some great Indiana Jones-style adventure with some nifty special effects (especially when the characters in a stained glass window come to life and start attacking).
If your young man has any interest in Sherlock Holmes, like I do (verging on obsession) he might also like the current modern version called Sherlock starring Benedict Cumberbatch. This version has amazingly quirky, intelligent, quick back and forth dialogue. The clues come at you like machine gun fire and it’s wonderful to watch “Sherlock’s” mind working like a computer to figure it out. It has a great ensemble cast too.
A more recent, very funny cult movie about teenaged life is Napoleon Dynamite Check out this funny clip of Jon Heder, the actor who plays Napoleon Dynamite on Letterman They really turned Jon Heder into an awesome nerd. In real life, he’s quite a cutie.