The 12 best scenes from Good Will Hunting, ranked
Good Will Hunting is an insanely rewatchable movie filled with insanely rewatchable scenes. I ranked the 12 best ones.
It’s fitting that Good Will Hunting is a Boston movie, because it has longevity that even Tom Brady would be jealous of.
Released in 1997 after an arduous process from page to screen — Matt Damon first started writing it as an assignment for a playwriting class, Ben Affleck helped him turn it into a thriller, Rob Reiner convinced the pair to ditch the thriller and focus more on the patient-doctor relationship, Terrence Malick gave them their ending, and finally, years later, Miramax (we don’t need to get into the Harvey Weinstein stuff, because it’s the worst part of the movie) put the film into motion — the movie still resonates as strongly as it did two-plus decades ago. It’s a movie that manages to provide meaningful commentary on brother-like friendships, romantic relationships, patient-doctor bonds, grief and loss, and fighting off your own internal demons, all at the same time. It’s been one of my five favorite movies ever since I first saw it at some point in the aughts. And it’s remained firmly in my top five with each and every subsequent rewatch. I reckon it’s one of my most rewatched movies of all time, even though I absolutely despise watching movies with characters named Sean. Seriously, Minority Report is one of my favorite Spielberg movies, but it’s a difficult rewatch because I have to listen to Tom Cruise yell SEAN! over and over again as he obsesses over his son’s disappearance. I’m right here, Tom.
But I digress. I’m not here in your inbox today to complain about fake people named Sean or to review Good Will Hunting or to provide a CliffNotes history of the film that you can read all about on its Wikipedia page. Today, I’m here in your inbox to rank the 12 best scenes from Good Will Hunting, because it’s an insanely rewatchable movie filled with insanely rewatchable scenes, and because I like ranking things.
Below, you’ll find 12 scenes from the movie, ranked. Just know that if I had additional time or space, I’d rank more than 12 scenes. There are more than 12 great scenes in this 126-minute masterpiece. But I was forced to leave some worthy selections out. Chief among them? This beauty.
As for the rankings themselves, if you don’t agree with the exact order, just know that it’s not your fault, you mathematical dick.
12. “Give us a kiss”
The first time Skylar (Minnie Driver) meets Will’s friends is essentially a double monologue scene. First, Chuckie (Affleck) tells the group a story about his drunk uncle who accidentally stole a cop cruiser. It’s a decent story, the kind of drunk story that is funnier to everyone sitting at the table than it is to anyone else, which makes it entirely believable as a drunken bar story. The shit we say at bars really isn’t that interesting. Its purpose is to introduce Skylar to the dynamic between Will and his tight-knit circle of friends as Chuckie and Morgan (Casey Affleck) exchange barbs.
It also tees up Skylar, who has a story of her own. Skylar’s story probably isn’t true, but it’s funnier than Chuckie’s. It’s meant as a way for her to win over Will’s friends. Anyone who has met a significant other’s group of friends all at once knows that it can be an intimidating experience. They all have inside jokes and talk in shorthand that you’re not privy to. It’s scary. You want to make a good first impression so that they don’t secretly hate you. Here, we watch Skylar overcome those obstacles and fit in seamlessly. It’s an impressive performance — by both Skylar and Driver.
But what I like most about the scene is Will, even though he seldom speaks. Watch his facial expressions throughout her story, because as much as Will’s friends are learning about his girlfriend, Will is learning just as much about her too. For as terrifying as it is for the girlfriend to meet the boyfriend’s friends, it can be equally terrifying for the boyfriend to watch the girlfriend meet the friends.
What is Will thinking? We don’t know. But I like to imagine he’s thinking about something his therapist, Sean (Robin Williams), said about idiosyncrasies. I also like to imagine he’s thinking about how he didn’t want to introduce her to his friends, because he was scared of making his relationship with her real and also because he feared what they all would think of each other. Halfway through her story, he realizes how wrong he was. That’s what I think he’s thinking.
11. “Re-taiiii-neeerrrrr!”
Ben Affleck is a leading man — his recent performance in The Way Back is Oscar worthy — but I tend to think he’s at his best (as an actor, not a director) when he’s not carrying a movie, but can play off other actors. He’s great as the lead in The Town, but Jeremy Renner does the heavy lifting. He’s phenomenal as the male lead in Gone Girl, but Rosamund Pike is the core of the movie. Good Will Hunting is my favorite Ben Affleck performance. He’s there to support Matt Damon. He does it exceptionally.
Later, he gets serious in the film’s best scene. Here, he shows off his comedic chops, posing as Will at a job interview Will doesn’t care about.
10. “It’s not your fault”
I’ll admit that I don’t think this scene hits as hard as advertised. It’s a necessary moment, for Sean to force Will to confront his demons, but it also doesn’t deliver the catharsis it should. The film’s emotional climax doesn’t come until later, when Will is healed enough to actually fight off his demons by chasing Skylar across the country. This scene allows Will to get to that point. It’s an important scene, but not the most important one.
9. “And the Oscar goes to …”
I’m cheating, but this is why I wrote “from Good Will Hunting” in the headline as opposed to “in Good Will Hunting.” Matt and Ben winning Best Original Screenplay remains my favorite Oscar moment, despite the now painful Weinstein shoutout. From Ben and Matt’s group hug with Robin Williams, to Ben’s opening quip about winning being “really scary,” to Matt silently pumping his fist to the crowd and smiling as Ben tries to compose himself enough to give a speech before the music plays them off the stage, to the chaotic ending, when Matt and Ben begin shouting names into the microphone (CHRIS MOORE!), Ben’s voice briefly goes through puberty, and Matt pumps his fist while screaming “YEAHHHHH!” Sowing Season style.
It’s authentic. Which really gets at why the movie works so well. Matt and Ben wrote the movie while living together in Los Angeles. They starred in it together, playing best friends as actual best friends.
That it was ever made into a movie is a minor miracle.
“It was odd that we even thought that we could do this, that it was something that was possible, that it would ever happen,” Affleck told GQ recently. “I think we were young enough and inexperienced enough to just sorta think ‘maybe it’ll work!’ instead of realizing how stacked against us the odds were.”
Against all odds, the movie cemented their status as Hollywood mainstays. This was really the moment that announced their arrival. If they ever make a movie about Good Will Hunting, it should end with this moment.
Over two decades later, despite some slumps, they’re still with us — and have a new movie (that they co-wrote) coming out in December, assuming movies are allowed to come out by December. By the look of it, it’ll either be the best or worst movie of all time.
I cannot wait.
8. “Your move, chief”
I’ll let Robin Williams take it away:
“If I asked you about art, you could probably give me the skinny on every art book ever written. Michelangelo. You know a lot about him. Life's work, political aspirations, him and the pope, sexual orientation, the whole works, right? I bet you can't tell me what it smells like in the Sistine Chapel. You never actually stood there and looked up at that beautiful ceiling, seeing that.
“If I ask you about women, you'll probably give me a syllabus of your personal favorites. You may have even been laid a few times. But you can't tell me what it feels like to wake up next to a woman and feel truly happy.
“You're a tough kid. I ask you about war, you'd probably throw Shakespeare at me, right? ‘Once more into the breach, dear friends.’ But you've never been near one. You've never held your best friend's head in your lap, and watched him gasp his last breath looking to you for help.
“If I asked you about love, you'd probably quote me a sonnet, but you've never looked at a woman and been totally vulnerable. Known someone that could level you with her eyes. Feeling like God put an angel on Earth just for you, who could rescue you from the depths of Hell. And you wouldn't know what it's like to be her angel, to have that love for her be there forever. Through anything. Through cancer. And you wouldn't know about sleeping sitting up in a hospital room for two months, holding her hand, because the doctors could see in your eyes that the terms ‘visiting hours’ don't apply to you. You don't know about real loss, because that only occurs when you love something more than you love yourself. I doubt you've ever dared to love anybody that much.”
This is the ultimate Robin Williams flex. For as funny as Williams is throughout the film, his ability to flip the switch and deliver this emotionally resonant monologue without overindulging is the key to the performance, which won him an Academy Award for Best Supporting Actor. For as well written as Matt and Ben’s script is, the film doesn’t work as well as it does without Williams’ contributions.
Not to mention, the movie never gets made without his involvement.
“Most people can’t point to the moment that changed their life in such a dramatic way, but I can,” Affleck told The Guardian a few years back. “It was the moment that Robin decided to take a flyer on that movie. I’ll always feel a huge debt to him although now I’ll never get to repay it. … If Robin hadn’t done Good Will Hunting, Matt and I would still be sitting there today talking about how we could update that script.”
7. “Why shouldn't I work for the NSA?”
Earlier, Robin Williams flexed. Now, Matt Damon gets to flex with a monologue of his own. It’s a funny speech involving phrases like “taking shrapnel in the ass” and featuring a deft cut from a job interview with the NSA to a therapy session with Sean, and it demonstrates how smart Will is, but what stands out about this scene is how much it reveals of Will’s mindset. It’s yet another glimpse into how his brain works. He always sees the worst-possible outcome in future scenarios. As Sean says later to Lambeau (Stellan Skarsgard), it’s a defense mechanism. He’s terrified of commitment, because he’s terrified of getting hurt, which is why he ends things with Skylar instead of moving with her to California and turns down job after job after job. He sees the worst in everything. To avoid disappointment, he refuses to commit. Will is obviously a smart thinker, but he’s also an overthinker. As much as the former is a strength, the latter is even more of a hindrance.
“You'll never have that kind of relationship in a world where you're afraid to take the first step because all you see is every negative thing 10 miles down the road,” Sean tells Will at a later point.
That’s what the movie is about, really. Will fears the worst-possible outcome in every scenario. Sean recognizes this, so he tries to get him to kick that habit even though the worst-possible outcome already happened to him when his wife died of cancer. Along the way, Will helps Sean put his chips back on the table.
6. “She used to fart in her sleep”
Fun fact: Robin Williams ad-libbed the line about his wife farting in her sleep, which might be why Damon laughs as hard as he does and the camera even shakes — the cameraman couldn’t help but laugh along. But for as funny as the scene is, Sean’s speech about “idiosyncrasies” and “imperfections” — “the good stuff” — is equally heartfelt.
“You're not perfect, sport, and let me save you the suspense: This girl you've met, she isn’t perfect either,” Sean says. “But the question is whether or not you're perfect for each other.”
It’s the first step toward getting Will to stop seeing the worst-possible outcome in every opportunity. The scene is the movie at its absolute best, funny while delivering a worthy and meaningful message. It’s yet another testament to Robin Williams’ acting ability that he can go from fart story to life lesson in a matter of breaths.
5. “How do you like them apples?”
If I were ranking quotes instead of scenes, this would be atop the list. Twenty-three years later, we’re still referencing it. Given the film’s longevity, I have a hard time believing we won’t still be referencing it twenty-three years from now.
I almost feel bad for Scott William Winters, who played Harvard Dick. I’ve seen him pop up now in two of my favorite all-time shows, The Americans and The Leftovers, in minor roles, and every time he’s on screen I can’t help but think about the time he got dunked on by Matt Damon in 1997 — to no fault of his own, of course. He was in only two scenes, but was so good at playing Harvard Dick in those two scenes that we all hated him immediately.
“Matt and Ben were really complimentary,” Winters told Boston Magazine. “Matt was like, ‘You know, dude, if you can find a way that gets you out of the room that’s more dignified …’ I really appreciated it, but I told them I thought that the way it was written was spot-on.”
4. “My boy’s wicked smart”
Among the most rewatchable moments in the film is Damon dunking on Harvard Dick for the first time in a Harvard bar. But first, we get to see Chuckie hit on Skylar by saying he took “history” class with her and telling Harvard Dick that he found the class “rather elementary” before Will steps in to help Chuckie out and demolish Harvard Dick.
“See the sad thing about a guy like you is in 50 years you’re gonna start doing some thinking on your own and you’re gonna come up with the fact that there are two certainties in life,” Will says. “One, don't do that. And two, you dropped a hundred and fifty grand on a fucking education you could’ve got for a dollar fifty in late charges at the Public Library.”
The most memorable line, though, is given to Morgan once Harvard Dick backs off and the dust disperses.
“My boy’s wicked smart,” he says in that Boston accent that all of us at some point have tried to mimic.
3. “Sonofabitch. He stole my line.”
I’m a sucker for a perfect ending that calls back to an earlier moment in the movie. Good Will Hunting’s ending is up there. It harkens back to Chuckie’s prior conversation with Will about “the best part of [his] day” and Sean’s story about the first time he knew when his wife was “the one.” Most importantly, it gives Will the happy ending Sean’s been trying to get him to want.
We don’t know if Skylar takes Will back. We don’t even know if that rinky dink car of his makes it all the way to California. But what matters is that Will is going for it. He knows there’s a chance he’ll fail, but for once, he’s willing to risk it. He sees the good in it.
The final line of the movie — “Sonofabitch. He stole my line.” — was improvised by Robin Williams. In that sense, the ending is the perfect blend of the script’s genius and Williams’ own original talent. It took both for the movie to become fully realized.
2. “October 21st, 1975”
I mentioned authenticity earlier. This is a scene that is soaked in authenticity. You get the feeling that during the writing process, Matt and Ben had a conversation about the biggest thing that Sean could’ve walked away from to have a drink with some random girl that ended up becoming the love of his life. Naturally, the two Boston sports guys came up with Game 6 of the 1975 World Series, a game that the Red Sox won in the 12th inning with a walk-off home run from Carlton Fisk.
The way director Gus Van Sant splices together the original footage from Fisk’s walk-off home run with Sean’s replication of the moment is filmmaking at its peak. I treasure how he switches from Fisk to Sean just as Fisk makes contact with the ball and Sean yells “BOOM!” and how Sean’s fake commentary narrates the original footage. It gives me chills just thinking about it.
“Gus definitely lent a maturity to the movie,” Affleck told GQ. “It was a little bit adolescent, a little bit naive in its original form, and because Gus was much older than us, much more mature, and more sophisticated, and kind of had a better sense of when we were pushing too far for sentiment or reaching for something, he definitely made the movie real.”
There’s a shot in this scene that’s my favorite shot in the entire movie, when the chairs in Sean’s office are turned into the diamond at Fenway as Sean rounds the bases like Fisk and bowls over Will the way Fisk bowled over fans who charged the field. It’s filmmaking at its finest.
The disbelief in Will’s face when he discovers that Sean skipped the game to have a drink with a stranger is precious. But Sean’s explanation is so genuine that Will eventually stops fighting him on it. He believes him the way Sean’s friends believed him when he told them that he was skipping the game. It’s also when we get to hear the “go see about a girl” line for the first time before Will steals it at the film’s conclusion.
Will: “Oh my God. And who are these fucking friends of yours? They let you get away with that?”
Sean: “Oh, they had to.”
Will: “What'd you say to them?”
Sean: “I just slid my ticket across the table, and I said, ‘Sorry, guys. I gotta see about a girl.’”
Will: “I gotta go see about a girl?”
Sean: “Yeah.”
Will: “That's what you said? And they let you get away with that?”
Sean: “Oh, yeah. They saw in my eyes that I meant it.”
Will: “You're kidding me.”
Sean: “No, I'm not kidding you, Will. That's why I'm not talking right now about some girl I saw at a bar 20 years ago and how I always regretted not going over and talking to her. I don't regret the 18 years I was married to Nancy. I don't regret the six years I had to give up counseling when she got sick. And I don't regret the last years when she got really sick. And I sure as hell don't regret missing the damn game. That's regret.”
Will: “Wow. … Would’ve been nice to catch that game, though.”
Sean: “I didn't know Pudge was gonna hit a homer.”
There’s something tragically fitting about that story. Sean doesn’t look back on his years with his wife with regret, even though he knows it ends in devastation. He cherishes everything that came before. Sean is also able to relive Game 6 as a happy memory even though he knows what happened next: The Red Sox blew a 3-0 lead and lost 4-3 in Game 7.
It’s yet another moment that helps Will understand that it’s okay to see where something goes even when you know it could end badly. The journey is worth it.
It’s the perfect blend of serious and funny, nostalgia and now, acting and filmmaking. For all those reasons, it’s my favorite scene in the movie, even if it’s not the best or the most important one.
1. “The best part of my day”
Ben Affleck rewrote this scene and rehearsed it for years, knowing it was his character’s and the film’s most important moment. Despite everything Sean had already told Will, Will needed to hear it from his best friend to actually have the guts to pursue a better life. It makes the ending hit that much harder, when Chuckie shows up at Will’s house and finds it abandoned, just like Chuckie wanted: “No goodbye, no see you later, no nothing.”
So, it was almost disappointing for Affleck when he nailed it on the first take.
“I remember vividly the scene where Ben tells me to leave town, where he says, ‘If you’re still here to come over and watch the Patriots game, I’ll fucking kill you.’ That scene, we did three takes on Ben. He got it in the first take and I knew we were done, we could go home,” Damon told Boston Magazine. “And he had this kind of stunned look on his face and Gus was like, ‘Would you like to do another?’ And Ben was like, ‘Yeah, yeah,’ so he did another one, which was great. And Gus said again, ‘Would you like to do another one?’ This has taken 15 minutes, at the most, for Ben to do these three takes. I was like, ‘Honestly, you got it on the first one.’ And he knew it, but he couldn’t believe that it was over.”
Affleck put it another way.
“I had been thinking about the scene and how it was gonna play out, and then reading it out loud, and writing it, and rewriting it, and rehearsing it in my mind over years and years,” he said. “It was just kinda like, ‘Is it over?’ It’s just hard to almost internalize the fact that, okay, we’re going to wait four years, and it’s gonna be over in five seconds. Kind of like losing my virginity.”
It’s not my favorite scene in the movie, but it is the best and most important scene.
I don’t know much. But I know that.