21 Movies Your Cool High School Boyfriend Loved


Cool high school boyfriends were always introspective. They were few and far apart, somewhere in that medium between obnoxious jock and pervy nerd. They were the intellectuals, the Jess Marianos of the world. They smelled most faintly of pot. Their paperbacks may have not fit their back pockets, but lord knows they read. And if you were a raging hormonal adolescent like myself, they were like demi gods. They weren’t the stars of the band or the drummer, but fell in the realm of bassist or rhythm guitarist. They had a lot to say, and you studied their philosophies like a good disciple. Early Nirvana had strongly inspired them, Nevermind was when they sold out.

They were always three years older and thought of sports as unnecessary exertion (skateboarding is not a sport, but a way of life). You listed his favorite movies as your favorite movies on Facebook, with Roman Holiday and Breakfast At Tiffany’s thrown in for your own introspection, and to skirt the fine line between babe and bro. You’d heard of half of these movies, seen only three but you loved Fight Club like a blind faith. In memory of the glory of our cool high school boyfriends here are 21 of their favorite movies, as listed on Facebook:

1) Trainspotting
2) Requiem For A Dream
3) Fight Club

Hallucinations, hallucinogens, vomiting into or climbing out of a toilet, English Skinheads and American Buzzcuts, Jared Leto, fighting for the sake of fighting, women as toys or sex toys or sex, early Psychedelic music and smatterings of the Pixies, at least one Irish accent and early Brad Pitt makes for the top three on the Cool High School Boyfriend’s list.

4) Boondock Saints
5) The Departed
6) The Godfather
7) Scarface

Is there organized crime conducted by deadly American immigrants? Is there a cocaine kingpin? Is there a twisted father figure? Is there at least one Irish-ish accent?

8) Brokeback Mountain
He and all of his Cool Boy Friends have seen this, alone and not together, and they will make Brokeback Mountain jokes that you just won’t get. Only in retrospect, this will raise many questions in your mind, or it will make perfect sense.

9) Road Trip
10) American Pie (Franchise)
11) Dude, Where’s My Car?

The Cool High School Boyfriend isn’t always so serious. He also likes to kick back from time to time and watch Seann William Scott get his prostate massaged, drink semen and never grow up, just to keep things in perspective.

12) Donny Darko

Time travel, vortices and a big, bad bunny rabbit. What’s not to love?

13) Star Wars

Let us not forget that he has a sweet and tender side, and that nothing is sweeter than a father who despises his son.

14) American Beauty


15) Vanilla Sky

Or “Why He Thinks All Women Get Attached And Become Crazy”

16) Lock Stock And Two Smoking Barrels
17) Snatch

Is it by Guy Ritchie? Is it an ensemble cast? Is Jason Statham the anti-hero? Is there a chase? Benicio Del Toro? Some form of skinheads? A crime lord? Early Brad Pitt (early Brad Pitt is crucial in the development on the Cool High School Boyfriend)?

18) Bad Boys 2

He has not seen Bad Boys, but only because he was inundated with homework in second grade.

19) Fear And Loathing In Las Vegas

What is it with your Cool High School Boyfriend and Benicio Del Toro?

20) Sin City

He is beyond reading graphic novels; remember, he is more introspective than that, and came into his own at the age of seventeen. But Sin City is more than just that. Not only was it the first time he realized he was actually in love with Jessica Alba, it’s also a neo-noir amalgamation of movies 1 through 19. And of course, Benicio Del Toro.

21) Forrest Gump

And as much as the Cool High School Boyfriend delights in tales of drug overlords, vengeance, betrayal, acid trips and public bathroom stall sequences depicting regurgitation and rebirth and Benicio Del Toro, he has a sensitive side, too, and he cries every time he watches Forrest, run.