15. Thomas Crown – The Thomas Crown Affair
I’m just gonna let y’all know right off the top: this is one of my favorite movies. The premise pretty much sells itself. “Bored billionaire playboy moonlights as a high-profile art thief, because golf is fucking boring.” I would watch that movie once a week, which is probably why I do. Let’s just look at some of Mr. Crown’s qualifications. He’s made billions by being a ruthless negotiator. He has his tailor come to his office to make him a suit on a regular basis. He steals a Monet because swindling other rich men out of their companies has become routine. He finds out that the woman sent by the insurance company to track down the painting is smoking hot (the hottest Rene Russo ever was), and decides that he’d rather seduce her than evade her. He makes Dennis Leary look like a dummy. He has a Rolls Royce for city travel, a jet for international travel, and an off-road 1967 Mustang to drive around on the island (a car that I swear I will own some day).
But the frattiest thing about him is the way he carries himself. The man is never surprised or shaken by anything that happens. He’s three steps and a hop ahead of everyone else at all times. He acts recklessly, not because he has to, but because he enjoys it. And that’s something we can all appreciate in our own lives.
14. Captain von Trapp – The Sound of Music
“God damn it, Cooper. You already put Pride and fucking Prejudice on this list, and now you’re putting Julie Andrews musicals on here?”
Yeah. I am. And you can go fuck yourself, because The Sound of Music is a beautiful and moving piece of cinema. But let’s go beyond the gorgeous cinematography and songs. We’re here for the frattiest dudes around, right? Well, look no further than Georg von Trapp. He’s a wealthy Naval officer in Austria who lost his wife a while back, leaving him with a whole bunch of kids to take care of. So what does he do? Take them out for ice cream and vidya game marathons? Hell no. He makes them his own personal military unit. They arrive and line up with whistles, obey his every command, and are all forced to wear the same thing. He literally turned his kids into pledges, but then Maria comes in and starts teaching them about feelings and favorite things and other bullshit, and he’s not having none of that. He then realizes that there’s another option.
He could bone the nun.
That’s right. Instead of just firing her, he figured, “What the hell, I could probably be a nicer father and seduce a woman with virginity vows.” That’s awesome. The Nazis then decide they want him to help them out. There’s about to be a war, you know, so he agrees, and then peaces out with his family, because a fraternity man, then and now, will always say “Fuck off” to the Nazis. To top it all off, he can sing like a fucking angel, but not one of those pussy angels — the kind with swords that fight demons and shit.
13. John Beckwith & Jeremy Gray – Wedding Crashers
I don’t know if crashing weddings was a thing before this movie, but it certainly was afterward. Sure, we all knew that our college friends’ weddings would be easy pickins for desperate women looking for male comfort, but to seek out the weddings of strangers with cover identities? That’s a whole other level, and these guys mastered it. They swooped in, dressed to kill, nailed their fake identities, charmed everyone from the flower girl to the grandma, and then flopped those gorgeous titties on the bed. Plus, they were in the business of irony, being divorce counselors who exclusively troll for pussy at weddings. But then they did what every loose, irresponsible fraternity man eventually does: they found the hottest daughters of the most influential man around and locked them down for life. Christopher Walken’s character must have been traced out of a fraternity alumni handbook. Rich, affected, clever, owns a sailboat, politician, has issues with his weirdo artist son, and he’s immensely protective of his daughters. The guy is a role model.
I’d also like to give a consolation ranking to Sack Lodge. Hell of a name, first of all. Secondly, if you really think back on it, was he really a bad guy? Really, the worst thing he did was not take his fiancée’s dreams seriously, but that’s just inconsiderate, not evil. Sure, he fucked over John and Jeremy, but rightfully so. They were kind of scumbags. And yeah, maybe he should’ve taken Owen Wilson one-on-one instead of having his boys hold him down, but the guy was trying to steal his lady. Oh wait, he was cheating on Rachel McAdams, wasn’t he? Forgot about that. Eh, we’ll call it a draw.
12. Pete Mitchell aka “Maverick” – Top Gun
Reckless, but the best. It’s a common movie trope, but not many characters did it better than Maverick. He disobeys direct orders about engagement in the first ten minutes to flip the bird to a Rooskie piece of shit. Can you keep up with a MiG 28 in a 4G negative dive while simultaneously giving him the universal symbol for “I’m better than you, asshole”? Didn’t think so. He serenades the woman of everyone’s desire in a bar with his boys. He fucks gently and majestically. He plays volleyball in jeans, because fuck you. I challenge you to find anyone in the history of America who pulls off a pair of aviators better. And let’s not forget that when shit got real, he put aside his rivalry with the doucher and teamed up for the sake of America.
Also, much like pledging and fraternities in general, Top Gun has been accused of having a good deal of latent homoeroticism. In both cases, I imagine the speaker to be an angry woman with spiky hair on a rant to a group of people which also includes a douche in a ponytail nodding his head slowly. I’m not saying she’s right or wrong, just that her and all her friends are shitheads. Anyway, what I’m trying to say is that none of us will ever fully get over the tragic death of Goose.
11. Billy Madison – Billy Madison
This is pretty straightforward really. He’s a hilarious adult who lives in the lap of luxury provided by his father, while he lounges in the pool, checks out nudie magazines, and runs around pulling pranks on GDIs with his jackass friends. For the record, anyone who calls the shit “poop” is a geed in my book. But he realizes that he has to step up if he’s gonna prevent that weasely chode, Eric, from taking over the company his pops built. And by step up, I mean go back and do grades 1-12. So no, he’s not climbing Everest or killing Nazis, but that’s not important. The stakes are real, and not only does he successfully complete school and kick Eric’s ass at the weirdest game of Jeopardy ever, but he also gets his teacher to fall in love with him, which is something we’ve all been trying to do since fifth grade.
In addition to how fratty the character of Billy Madison is, we also need to consider how much influence the movie itself has had on the fraternity men of our generation. Think about how many of our jokes and conversations involve quotes or ideas from this movie. A lot of times we probably don’t even realize it. That’s why I’m including not one, but four of my favorite Billy Madison quotes. Why? Because I have the room to, and I feel like it.
“Actually, I uh, stole this shirt from Frank.”
“If your dog gets lost, you don’t look for an hour and then call it quits. You get your ass out there and you find that fucking dog.”
“Touch her boobs? That’s assault, brotha.”
And how many undergrads’ faces have you squeezed while whispering, “Stay here as long as you can. For the love of God, cherish it. You have to cherish it.”
So there it is, boys. We’re cracking into the top 10 next week. Get your dicks ready.