Would You Rather: Matt Damon or Ben Affleck

Life often presents us with tough choices, but we’re here to help work them out. Each week, we discuss two attractive men, weigh the pros and cons, and decide, once and for all, which one we’d rather have sex with. In this week’s Would You Rather, we discuss two ’90s indie heartthrobs turned Hollywood leading men: Matt Damon and Ben Affleck.

Tyler: Joel, I assume you were born in, like, 1995 or whatever, so you cannot possibly know what it was like to be a 14 year-old gay kid when Good Will Hunting came out in 1997 and practically introduced the world to the charming duo of Matt Damon and Ben Affleck. Sure, they had both appeared in movies before their breakthrough film, for which they won Oscars for Best Original Screenplay, but it definitely established the pair as the indie wunderkinds who would later go on to be suave leading men. What a treat it was, then, to have these two adorable guys serve as the original Would You Rather — or at last, the round I first played inside of my head. Which could I have possibly picked? They both seemed to have everything I wanted!

Joel: I’ve never seen Good Will Hunting, but that never stopped me from uttering “how do you like them apples” frequently and without any context at all throughout the mid to late 90s. I would later famously confuse this movie with Finding Forrester (another movie I never saw) while giving a presentation in a college class. I still graduated, but I still have never seen either of these movies. All this is to say: I honestly don’t associate these two as some kind of duo in my brain. Ben Affleck will always just be Daredevil and Matt Damon will always be The Talented Mr. Ripley. Sorry!

Tyler: Well, to continue with my train of thought, the years have made my love for both of these guys go in different ways. Matt Damon seemed to be the dominant, smarter one of the two — he did star in Good Will Hunting, after all — and he seemed like the brains behind the operation. (There’s a bit that Colin Quinn did on Weekend Update in which he imagined Ben Affleck slaving away over the typewriter while Matt Damon stood in the window, shooting people with a sniper rifle a la Ralph Fiennes in Schindler’s List.) And while Ben Affleck’s intelligence is still questionable, it’s clear that he’s not a complete idiot. He does, after all, have three director credits under his belt, and one of those movies, Argo, won Best Picture. What I’m saying is, I’ve gone back and forth with these two in my head over the years, which really broadens the definition of “flip-flopping” here, huh?

Joel: Read that paragraph back again, Tyler and then ask yourself a very important question before we move ahead with the debate today: is this the weirdest thing we’ve ever done? I mean quite honestly, I found myself nodding my head in agreement upon reading the sentence “Matt Damon seemed to be the dominant, smarter one of the two” even though we really have no idea if this is true or not. When we do imaginary people, there is some additional context, some inner life we can examine. But is it even possible to accurately discuss the merits of two real-life humans who we don’t know? Should we be concerned about ourselves?

Tyler: We’re only human, Joel. This is all we’ve got. Anyway, let’s get right to it: which of these Boston boys would you bone?

Joel: I’m a classy broad, with classy tastes, so obviously I’m going to choose the classier of the two, Matt Damon. Even as he’s grown into prime Cool Dad Matt Damon, he’s still maintained a lot of that boyish charm that he exuded back in the early days of his career. Ben Affleck, who to be fair seems like a pretty cool dad as well, just doesn’t do it for me. He’s an attractive man as Hollywood stars go, but he always looks like he’s on the run.

Tyler: David Fincher would agree with you. This one is very difficult for me. For most of my life, the answer was always Matt Damon. He was the smart one, the clean-cut one. The one who’s ass I couldn’t stop staring at in the otherwise annoyingly stupid The Talented Mr. Ripley. (Seriously: I have given that movie TOO MANY TRIES.) His boyish good looks always worked for me, and when he got older — and he got thick — I was still on board. And then I saw Gone Girl, and something switched inside of me. Probably the side peen? Yes, it was the side peen. And also the muscles. And also how he seems kinda like a dirtbag. I know I usually say in this column how I don’t like a challenge, but I’d be willing to accept this one. Ben is for me.

Joel: I’m not surprised. No offense, but you definitely seem like the type who would be swayed by a little side peen.

Tyler: Uh, you go back and find that GIF because we’re not talking about a little anything.

Joel: Fair point. If you’d have let me finish, I was going to say that it was a magnificent side peen! America’s very favorite side peen! But honestly in looking at their body of works, and just their bodies in general, I’m still going to favor Matt Damon. It’s true I’ve never seen the side of his penis, but he’s been consistently hunky for the past decade and a half which points to continued hunkiness for the foreseeable future, and just makes him a better investment.

Tyler: It’s true. I don’t disagree with you! But I think this pairing, and my feelings toward both of them, represent my evolution as a human being. You know that thing about how your body’s cells replicate every seven years or whatever? (Science, Joel.) And how you’re a completely different person than you were seven years ago? Well, I think that seven years ago my answer to this question would be Matt Damon, no contest. But there’s something about Ben Affleck’s ego and narcissism that compels me. Starring as a Mexican-American in Argo (and making a point to show off his abs for no good reason)? Into it. Getting banned from casinos for card-counting? Not even Damon’s Ocean’s Eleven character is that ballsy? Shutting down production on Gone Girl for days because of a Yankees cap-fueled temper tantrum? Man, that’s the kind of unstable jerk that I want to let loose in my bedroom. (Plus: those Batman muscles. Yes, please.)

Joel: If you think any of those things rolled into one human amount to “great sex,” you are disillusioned past the point of reason. You know Matt Damon is the better one in the sack. He’s the funny one! Remember his turn on 30 Rock? He was hilarious and self-deprecating. If anyone could do with a little self-deprecation it’s Affleck. The man, despite his many talents, has starred in some historic flops, and by all accounts should be thankful for the wealth of work he’s received despite it. Why is he so touchy? Why won’t he laugh with us? To be fair, I will burst into tears as soon as someone tweets something nasty to me about this piece, so.

Tyler: I am thinking purely with my libido here. I do not want to marry Ben Affleck. I do not want to cuddle with him afterward. I don’t expect him to stick around long enough anyway. But aesthetically speaking, Affleck’s the one I want to have no-strings-attached sex with, for sure.

Joel: Well we’re all certainly entitled to our wrong opinions. I still feel like sex with Ben Affleck would be the sort of like fucking a grunting slab of pizza dough. No offense to him. He’s a man of immense talent. But more important question: while we usually pivot at the end to discuss the other men who inhabit the fictional worlds of our subjects, that’s obviously not possible here. I guess can we just talk about how we feel about Casey Affleck?

Tyler: There are no other Afflecks as far as I’m concerned. But maybe you should tell me which Matt Damon is the most fuckable for you?

Joel: Truly any Matt Damon that doesn’t have a nightmarish pony tail attached.

Tyler: Oh, I’d probably still have sex with that Matt Damon. Or Matt Damon in The Rainmaker, because I do love a Southern boy with a heart of gold.

Joel: You’ve made your choice, Tyler. You can’t have them both.

Tyler: Fine! Then I pick Ben Affleck in Reindeer Games. PEAK AFFLECK!

Joel: You disgust me on a lot of different levels.

Tyler: It’s why I’m here.

PREVIOUSLY:
Steven Hiller vs. David Levison from Independence Day
Peter Florrick vs. Will Gardner from The Good Wife
Captain Kirk vs. Mr. Spock from Star Trek
Luke Danes vs. Christopher Hayden From Gilmore Girls
Mark Cohen vs. Roger Davis from Rent

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Photos: Everett Collection