Ben Affleck’s Redemption Story: A Tale of Perseverance and Second Chances-HO

It’s one of those endless blue-haze days in Los Angeles, and Ben Affleck is leaning back on the diving board of a borrowed Bel Air estate to catch the sun, his long torso arced like a bell curve. For a moment it seems like he might actually fall in, bringing a precariously perched photographer and several yards of creamy, expensive-looking knitwear with him. But his balance is better than it looks: Affleck, 49, has walked the plank many times before, and tumbled from greater heights than this. He’s also climbed back up again, a story of outsize stardom and second chances played out in the public eye for nearly three decades now.

After a mid-career swerve toward directing films like Gone Baby Gone, The Town, and Argo (for which he won Best Picture), the actor has returned to his first love, turning in fresh, revelatory performances in Ridley Scott’s medieval epic The Last Duel and George Clooney’s warmhearted drama The Tender Bar. To mark the occasion, Affleck’s erstwhile creative partner and oldest friend in the business, Matt Damon (it’s been 24 years since they took home their Best Original Screenplay Oscar for Good Will Hunting, how do you like them apples?), sat down to discuss life, love, and all the roles — School Ties, Armageddon, and yes, even Gigli — that made the man. —Leah Greenblatt

Ben Affleck on Entertainment Weekly’s February 2022 cover. GUY AROCH FOR EW

MATT DAMON: Ben Affleck, it’s great to see you here today.

BEN AFFLECK: Hey there, man! Welcome to the red carpet. Before we get into your project, who are you sleeping with?

[Laughs] Well we’re here to talk about The Tender Bar, a movie directed by George Clooney which you star in. I guess I first became aware of it when you called me very excited that you read a great script that Bill Monahan wrote and George offered you a job. I promptly called George and he said that it was because you were cheaper than me. But as the month went on, I started to wonder if he was telling me the entire truth.

He told me that you argued too much. “I got tired of dealing with Damon’s bull—-. You’re gonna do what I tell you, right?”

How was I going to just take his notes and not say anything? But you said you received some of the best direction of your career from Georgie, so I was wondering if you could help people understand what that means.

Well, to begin with, because of your collaboration with George, and my own experience working with him, I had a strong rapport with him and held him in high regard. You’ve consistently demonstrated astuteness in selecting exceptional directors, and it’s been fortunate that talented directors have recognized your abilities. I recall how you recognized this early on and how it greatly benefited you. George was someone you always spoke highly of.

So, apart from feeling a pang of envy and grappling with feelings of inadequacy and self-doubt, I couldn’t help but think, “Wouldn’t it be nice if that happened to me one day.” So when he unexpectedly reached out to me — you know how rare it is for a polished, excellent script to come along with a truly exceptional director attached, and all you need to do is be present and agree.

I mean, especially today, right?

Yeah, I knew that this was kind of mine to screw up. I couldn’t imagine there wasn’t a long line of people that wanted to take this part, so I really respected his confidence and faith in me, and I wanted to do well for him. I wanted to do it for myself. There’s an emotional scene in the end where I give the kid [Tye Sheridan] a car, and every time I read the script, I cried. So I showed up and I really got ready and did my thing. We did the first take and I thought, God, this is it. This is all working. George came over and he said, “Yeah… Giving a car to someone is supposed to be fun.”

That’s what he said?

I was like, “Right, yes, of course. I’ve been playing it completely wrong.” Other directors can talk to you for an hour and a half and it doesn’t seem clear what they’re driving at, whereas George has this gift of succinctness and insight. But also just being directed by somebody who’s done this job that I’ve been trying to do for, I don’t know, 30 years, is such a comfort and a relief…. My dad worked in a bar, as you know. All that stuff was very familiar to me. So my only concern was, “Should I be working harder than this? It shouldn’t feel this smooth.”

I’ve always said, as an actor, your only excuse for not being good is “I didn’t know what movie I was in.”

It’s interesting, because that was the very first thing George did. I mean, a director’s job in large measure is tone. Is it more comic? More serious? For me, every time I work with a director that I really admire, and even some I don’t — I can learn from negative examples, too — but I just feel like I become a much better director.

I remember Francis [Ford Coppola] sold these little cigars at his winery that are called Carmine Thrifties, they’re named after his father. And on the side of the box, it says, “Steal from the best.” Which brings me to my next question: Is there anything you’re going to carry forward into your own directing coming out of this experience?

I think it’s hard to overestimate the degree to which a director’s attitude, openness, comfort, generosity pervades the set and sets a tone. George does that better than I do. And he was enormously respectful of the degree to which I take very seriously my need to be there with my children for my half of the custody. I mean, he bent over backwards. You didn’t have to be there until midnight every night [or] obliterate the rest of your life in order to do this. Because he’s got this spectacular wife, he’s got his children, he’s got a very rich, full life. He’s got to sell coffee—

He sells tequila, too.

Tequila and coffee. That’s no joke.

He’s got you in the morning and the night.

I’ll tell you what I want to be. I want to be George Clooney selling coffee and tequila. Because that really frees you up to do the movies you want to do.

So speaking of awesome actors, I’ve been tasked with going all the way back to the beginning of your career.

Don’t be afraid to relieve yourself of some of that burden, if it feels unduly burdensome.

I take my job very seriously here at Entertainment Weekly.

That’s what I’m afraid of.

Ben Affleck. GUY AROCH FOR EW

But before we go back to where it started, let’s talk for a second about where you are. Do you attribute it to just, “You play in traffic long enough, you’re bound to get hit by some cars?” Is that why your performances are so good of late? Like what you did in The Way Back and The Last Duel. It’s full, it’s rich, it’s invested. It’s right. And you’re not reaching.

Thank you. That means a lot. Sometimes people will go, “You know, you’ve really gotten better as you were older,” which sometimes feels like “You’re not that bad-looking in person! You’re not as stupid as I thought you were!” I have some performances as a younger person that I really liked. I knew [Good Will Hunting‘s] Chuckie Sullivan. I felt an affinity for Ned Alleyn in Shakespeare in Love, and really connected with the character in Chasing Amy.

Changing Lanes! You were great in that one.

That’s where I met Bradley [Cooper], actually. Starting off, you have these ideas about success. You know, my mother made $28,000 a year. So I would be like, “How could I justifiably say no to this?” Just not understanding the value of turning things down. People talk about your choices and I want to say, “Well, it’s not like I was passing on Scorsese movies.” Like, “No, Marty, I’m good. I’m going to do Surviving Christmas.” Part of our fates are controlled by the opportunities we have in terms of material and directors.

Absolutely.

That’s a significant observation. I’ve always found myself more drawn to portraying characters who deviate from the conventional protagonist archetype. You excel at this far more than I do, and it’s not a veiled compliment; rather, you have a knack for rendering characters intriguing, flawed, and authentic. As a storyteller, it’s imperative not to estrange the audience from your protagonist. Otherwise, you’re left with a film featuring a character viewers either judge, dislike, or find unbelievable, which undermines the entire narrative.

Playing the role of the leading man is deceptively challenging. Take Denzel Washington, for example; he possesses an innate charm that makes you inherently like him, aspire to be him, and admire him. That ability to captivate an audience is crucial. One of the perks of aging, if you’re fortunate, is that you cease deceiving yourself and begin acknowledging your true emotions. The more I’ve come to understand myself, the more accessible those emotions have become. I comprehend what pain feels like, what disillusionment entails, what ambivalence is, and even what nostalgia evokes.

Right.

I went through a really tough time around the production of “Justice League” for various reasons. I’m not placing blame on anyone; there were many factors at play. But fundamentally, I was unhappy. I didn’t enjoy being there. I didn’t find it stimulating. And then some truly awful things happened. That was the moment I decided I wouldn’t subject myself to that anymore.

In fact, I discussed it with you, and you were a significant influence on that decision. I wanted to pursue things that brought me genuine joy. So, when we embarked on “The Last Duel,” I found pleasure in every moment of filming. I wasn’t the protagonist, I wasn’t particularly likable—I portrayed a villain. I didn’t embody all the qualities I thought I was supposed to when I started out, yet it was a remarkable experience. It was all opportunities that came my way without me actively seeking them.

My only concern now is that with each new project, I worry: “Do I still have it? Am I still capable?” I fear that feeling might disappear because it’s fleeting. But presently, I’m content. I’m experiencing it now. And I do believe I’ve improved. I think people generally become better with age and experience—

Some might not. They might get in really bad, corrosive habits.

If you’re smart, you learn from people who are really good. And I think our friendship helped kind of inculcate that knowledge in me. We were very generous and open with stuff. Being around other people that you liked and respected and were smart just made you better.

Ben Affleck. GUY AROCH FOR EW

You said to me and I’ve always repeated it — I mean this is when we started writing together, you were 20 and I was 22 — really starkly, you were like, “Judge me for how good my good ideas are and not how bad my bad ideas are.”

Everyone’s got bad ideas. Like David Fincher, who is brilliant, every now and again, you go, “Hmm, I don’t know.” But then you find out he has the humility to go, “Oh, huh.”

I remember that with the Coen brothers, more than once. One of them would come up and give me a note after a take and then the other one would be off talking to another actor and would come up and give me the exact opposite note. And without fail, I would always say, “Joel, Ethan just told me the opposite thing,” or “Ethan, Joel just told me to do the opposite thing.” And no matter who it was, the second guy would say, “Oh yeah, do what he said.” [Laughs]

Let me ask you a question about the business before I start running these old movies by you. Given The Last Duel, which I’m drinking my tea and shamelessly promoting with a Last Duel mug that I made…

Did you hand-paint it? Matt Damon, hold the mug!

Obviously it was a box office failure. But interestingly enough, it’s number one on iTunes. So it means that there is an audience, just one that was unwilling to go in the middle of a pandemic to the theater. How does that make you feel, coming out with another drama — did COVID just accelerate something that was going to take 10 or 15 years, or is it coming back?

I won’t mince words because that’s always dull. When “The Way Back” was released, it coincided with the closure of theaters due to the pandemic. However, even before that, I had a feeling that a film centered around themes of grief, loss, alcoholism, and recovery wouldn’t necessarily draw adults to theaters. We were just discussing the captivating content available on streaming platforms like “Narcos: Mexico,” “Succession,” “Mare of Easttown,” and films like “Roma.” It’s not merely formulaic TV procedurals like what we grew up watching, often on tiny black-and-white screens like my dad’s 11-inch TV.

If I had to make a wager, a drama like “Argo” wouldn’t secure a theatrical release in today’s landscape. It would likely be developed as a limited series. I foresee theatrical releases becoming more expensive and focused on event-driven experiences, catering mostly to younger audiences who are enthusiastic about franchises like the Marvel Universe. There might be around 40 theatrical releases annually, primarily consisting of IP-driven content, sequels, and animated films.

“The Last Duel” was a turning point for me. I’ve experienced disappointment with films that didn’t resonate, and I understood why they didn’t connect—they simply weren’t good. However, with “The Last Duel,” I believed in what we created. I’m proud of it. So, I was perplexed initially. But seeing its success on streaming platforms affirmed my belief that’s where the audience is heading.

Ben Affleck. GUY AROCH FOR EW

Heading back into a time machine now—

If I thought I was going to be held accountable for these movies 20 years later…

Thirty years, dude. Thirty. Let’s start with School Ties because that was the first time we did a feature film together. What do you remember?

I knew my nine lines back to front. I loved every day I was on a call sheet, every day I got to come to work. You were there, in Boston. It was one of the best experiences of my life.

Even by the dump in Lowell. Remember?

We literally were next to a dump and thought we were kings. I knew I was playing the one s—ty anti-Semitic bully character, so I figured it was probably not going to be great for me career-wise, but I loved it.

I wasn’t in this, but Dazed and Confused, that was your first time working with and meeting Rick Linklater and all those guys.

He served as a role model for us when we looked around and realized, perhaps for the first time, that we could make our own movies, you know? Films like “Reservoir Dogs,” “Slacker,” “Clerks,” and “Do the Right Thing” demonstrated that people were creating outside the traditional system, and that was incredibly inspiring.

Picture this: a group of 19-year-old kids filming night scenes at a party in Texas. The lines between our time at the hotel and on set were blurred. I got to know Matthew [McConaughey] in the early stages of his career. Rory [Cochrane], I’ve remained friends with, and he even appeared in “Argo.” Anthony Rapp, Joey Lauren Adams, and Renée Zellweger—there was just an abundance of talent.

Then came the disappointment. It bombed. Bombed! Hardly anyone saw the movie, despite receiving rave reviews. I remember reading a review from Owen Gleiberman saying something along the lines of “Once every decade…”—I thought it was an exaggeration. But it turned out to be true. It’s become a true cult classic that people still discuss, and I’m grateful to have been a part of it. Once again, I found myself playing the solitary unlikable character in a film filled with immensely appealing people. So, not exactly a standout moment in my career. [Laughs]

Well now, speaking of DIY filmmaking: Mall Rats. You obviously have got to talk about Kevin [Smith], but maybe fold them all in because you’ve got Chasing Amy, too.

I was, once again, playing the bully, running around, throwing people into their lockers. But I liked Kevin. He’s funny and smart and charming. We got along.

Kevin also saved Good Will Hunting. This is not a small side note. He is the reason Good Will Hunting got made. We were dead in the water, all the offers had evaporated.

I promised him I would thank him if we ever got an Oscar and promptly forgot. And then I told him, “If I ever win again I swear to God I’m going to thank you.” Forgot again.

Kevin and Gus [Van Sant, Good Will‘s director] and Robin [Williams] were equally important. And I think Francis [Ford Coppola] vouched for me with Robin.

God, he was a wonderful guy. And funny! It was the first time I ever got to hang out with somebody that talented and that famous. I remember walking down the street in Boston with him, he had done Good Morning, Vietnam and Awakenings and Fisher King and all that. And all everybody in Boston would say was “Nanu, nanu.”

Yeah.

Mork from Ork.

Mork! But he did do that — he would just do take after take after take because that beautiful brain of his would always come up with something different to do…. So from there, I remember when you got Armageddon. We got split where people went, “Oh, well, Ben’s the big movie guy. And Matt’s the serious guy,” because I did Saving Private Ryan. But the fact was that we were desperate to get another job, and I would’ve happily taken Armageddon. You would’ve happily taken Saving Private Ryan. I remember I was shooting [The Talented Mr.] Ripley in Italy when that thing opened, and it was a massive hit. That was a terrific cast.

Yeah, Bruce Willis, Owen Wilson, Billy Bob [Thornton], Mike Duncan. This was real Hollywood, which I felt like I had never seen. They dug out two stages of Disney for huge asteroid craters, and I didn’t even think about the fact that the basic premise of the movie was totally absurd.

Why are they training oil drillers to be astronauts rather than astronauts to be oil drillers? You would think the learning curve would be somewhat more steep on the oil-drillers-to-astronauts route. But it was fun and the right time. It’s funny, Bruce dropped out of a movie, and as the deal for dropping out of this movie that wasn’t working is that we get to put you in two movies, and they put him in Armageddon and The Sixth Sense.

Oh my God, really?

Yes! And I was a little naive about the opinions people would form about me. Or Michael [Bay] and Jerry [Bruckheimer]’s focus on aesthetics, like, “You guys gotta go to the tanning bed!” They made me fix my teeth and work out and be sexy. Be sexy, how do I do that? “Go to the gym!” Running in the gym and putting oil on my body and stuff, and it just turned out to be a long-form version of one of those male topless calendars, in a garage, carrying a tire, kind of greased up. Michael had a vision of a glistening male torso in the oil, and he was like, “That’s going to go in the trailer and sell tickets!” And you know, what can you say? We could have made, I think, 400 Chasing Amys for what we made Armageddon for.

It’s funny because that’s the one movie of mine that my kids have watched and they’ll kind of all admit to liking, even though they relentlessly mock it and me. “What are you, driving a tank on the moon?” But they had fun, you know what I mean? They won’t even watch The Town. So there you have it.

Ben Affleck. GUY AROCH FOR EW

My kids won’t watch my stuff, either. All right, wow, they have a lot of movies they want me to ask you about.

Skip to the ones that are interesting.

Let’s touch on Gigli because it’s directed by one of our favorite directors, Marty Brest. Where does it sit with you now?

You know, it’s an interesting thing because it was a really easy choice. I loved Midnight Run. I loved Beverly Hills Cop. I loved Scent of a Woman. Marty’s obviously enormously gifted. There’s no question in my mind that this was a guy I wanted to work with. There was wonderful stuff in there. There are things where my daughter will be like, “This is ableist and disgusting,” and okay. The way we see stuff has changed a little bit, or a lot in some cases. And there are things that seemed they could work at the time and don’t in retrospect.

But really, the truth about that movie and what it taught me was how much everything around a movie sort of dictates the way people see it. But for being a movie that’s such a famous bomb and a disaster, very few people actually saw the movie. It doesn’t work, by the way. It’s a sort of horse’s head in a cow’s body. And the studio at the time, because I had begun having this relationship with Jennifer Lopez, which was selling a lot of magazines and appeared to generate a lot of enthusiasm, they just predictably latched onto, “They want a romantic comedy. They want the two of them together. More of that!” And it was just like that SNL sketch: “Bad Idea.”

But even movies like The Sum of All Fears that worked commercially but didn’t have any depth to them, I didn’t do anything particularly interesting in them. [Gigli] didn’t work and we did five weeks of reshoots, which we knew were not gonna work. It was a movie that didn’t work…. Interestingly, I learned more about directing on that movie than anything else because Marty is a brilliant director, really gifted. It’s not like it’s worse than all… there’s a bunch of horrible movies and in terms of losing money, I’ve had five movies — at least! — that have lost more money than Gigli has.

It’s just that it became a story in and of itself. The funny name, the Jennifer Lopez romance and overexposure of that, it was kind of a perfect storm. And I remember talking to Marty the Friday it came out and I was like it’s just spectacular, it’s a tsunami, it couldn’t be worse. This is as bad as it gets.

I thought my job was to be a cipher. I can see now how people looked at me and thought of this person as some callow frat guy who’s cavalier, or has too much. It engendered a lot of negative feelings in people about me. There’s that aspect of people that I got to see that was sad and hard, it was depressing and really made me question things and feel disappointed and have a lot of self-doubt. But if the reaction to Gigli hadn’t happened, I probably wouldn’t have ultimately decided, “I don’t really have any other avenue but to direct movies,” which has turned out to be the real love of my professional life. So in those ways, it’s a gift. And I did get to meet Jennifer, the relationship with whom has been really meaningful to me in my life.

I remember you saying to me at that time — probably around the opening weekend, and I never forgot it — you said, “I’m in the worst possible place you can be. I can sell magazines, but not movie tickets.”

Yeah. I remember feeling like it was the worst of both worlds. I always viewed it that the tax you paid to get the chance to do this work was to sacrifice your private life, and people were going to have license to make sport of you to some degree. And I didn’t go into it blindly. I knew that Sean Penn and Madonna were a tabloid story when I was young. I knew that could happen. Jennifer and I happened to be together at a time where the whole industry of celebrity journalism, if you want to call it that, sort of exploded. But I thought, “S—, this is really not how I had hoped to go, where I’m going to be, what? Famous for being an a–hole or a failure and not able to work?”

I can’t think of a worse outcome. Because I’ve never found any virtue in fame at all. I’ve probably gotten out of a couple of [traffic] tickets. I’ve gotten reservations at restaurants. But the whole point was to be able to do this job. That was it. Otherwise, what is it worth? It’s corrosive. It changes the relationships you have with other people. But one of the things that time showed me is that it is those moments of crisis or pain or perspective that are strong enough to make you go, “F— it. Well, this doesn’t work. I’ve got to do something different.” I’ve definitely learned more from failure than I have from success.

Ben Affleck. GUY AROCH FOR EW

Yeah. Well, we’re not ending on the note of failure because the postscript to the story is, after 2006, you became a world-renowned director. You won an Academy Award for Best Picture, which is really the highest mountaintop in our business. I’m wrapping this up because I’m late for dinner. My kids are staring at me through the window.

I know how it goes.

But you’ve had a remarkable last decade and a half that is culminating with some of your best acting work that you’ve ever done and The Tender Bar is another example of that. And I dare say your writing is pretty damn good. I was really proud of the work you did on The Last Duel.

I love you, man. I want you to do all my interviews. Are you cheap? [Laughs]

I’m free, actually. I’m free.

To be honest… Thank you. It’s true, it ends on a much happier note. Not easy and not always smooth, but good. I don’t know that that would’ve been possible for me alone, doing this job in this world without somebody I grew up with who I loved, who I knew loved me and had my back, who believed in me, and whom the popularity of my movies or what people said about me wasn’t going to change what they thought about me.

This friendship has been essential and defining and so important to me in my life. There were a few critical times, which are private and I don’t want to share, but where your support was so profoundly meaningful to me that I don’t think I would’ve been able to be successful without it. So let me take this opportunity to thank you—

—in a Zoom interview. [Laughs] Congratulations on another great piece of work, and I hope people go see The Tender Bar. We’ve just got to get people to see the movies.

Well, that may go away, but we’ll always be good. And we’ll finally have figured it out when we hit the dinner-theater circuit.

We’re each a fan club of one for the other. All right, man. I love you.

I love you, buddy.