Ben Affleck Still Feels Imposter Syndrome After Two Oscars, Reflects on ‘Air' Success

Air, which made its theater debut in early April, will hit Prime Video on May 12.

The film was well-received by both fans and critics alike. Its creators Ben Affleck and Matt Damon and the cast exhausted themselves with an impressive, but grueling press run that paid off, delivering an impressive $20.2 million at the domestic box office on opening weekend, and a worldwide total of $80.8 million a month after its release. It may not have gotten back the $90 million budget Amazon Studios spent on it, but it surpassed expectations. The film was made for Prime Video, so the studio originally did not initially plan to turn a profit with a theatrical release.

In every interview, it was clear that Affleck, who directed the project and stars as Nike CEO Phil Knight, believed in the story they were telling and was intentional about every aspect of the film. With a script from writer Alex Convery that was inspired by the Michael Jordan documentary The Last Dance, Affleck set out to tell the story of the inception of the now iconic Air Jordan brand and sneaker. Air is by no means a biography about the NBA legend, but more so a behind-the-scenes look at what it took to close the most impactful deal in sneakers history.

Damon excels in the film as Nike executive Sonny Vaccaro, who along with Deloris Jordan, was the mastermind that brought Jordan’s first sneaker deal to life. Affleck has been open about his approach and how he never intended to make this story one that took away Jordan’s ability to tell his own. He tapped the basketball star for his input—which included making Viola Davis play his mother Deloris and adding key players like Howard White (Chris Tucker) who weren’t part of the original script. Affleck obliged to Jordan’s requests, and it all worked in his favor.

Regardless of Air’s critical and box office success, Affleck seems largely unaffected and unmoved by it all, except he refers to it as “the best experience professionally” of his life. Affleck tells Complex that no matter his accomplishments or accolades (which include two Oscars), he still feels like the phone could stop ringing at any moment.

“What I’ve discovered is that the idea that outside approbation or approval is going to fill the place in you that is anxious or wanting or feels like it has something to prove. It doesn’t actually do it, strangely enough,” the director says. “You have these moments that are supposed to create that feeling in you and I think one finds that it generally doesn’t. It’s not lasting, that the things that last in life are not the totems or trophies or ribbons.”

Now that Air is making its streaming debut, Complex caught up with Affleck for an introspective conversation about the film’s reception, his intentions behind making the Jordan-inspired flick, and why he still feels uncertain about his career after all these years.

It’s been some time since the movie hit theaters and the reactions and response from people have been, from what I’ve seen, amazing. How did you feel when you got to see people sharing their thoughts about it?

It was really, really unusually satisfying. I don’t often take a lot of, probably not enough, healthy amount of pleasure and things that go well given that this business is a lot of ups and downs. But in this case, I really felt like I was sitting on a kind of creative treasure trove of performances and that I would share with people and I was like, “Gosh, everyone was really so great.” I really wanted it to come out. And I was so glad that it’s now in theaters and people enjoyed it together and see theaters that are full and laughing. And it was a very, very deliberate attempt on my part to make a movie that people would enjoy, you know?

The kind movie that I’m interested in, which is movies that are cinematic certainly, but that are rooted in, what’s interesting about it is the empathy and passion you develop for the characters and I wanted to make a movie like that. But one that was kind of unabashedly a celebration, kind of an homage, a gesture of esteem to Deloris Jordan and Michael Jordan and who they are and how they changed the industry and ultimately the world, in effect. And I thought it was a wonderful story and it was an interesting opportunity to have the audience think that you had one protagonist for two-thirds of the movie and then find out somebody else was actually the lead of the movie. That was an interesting experiment and I was really glad to see that people went along with it. So it was thrilling.

I definitely went into the film myself expecting more Ben and more Phil Knight, but then I was pleasantly surprised when I saw Matt [Damon] just take over. He was so captivating in this movie. As his director and as his friend, what did you learn about him as an actor during this project?

I learned a deeper, more full appreciation for how good he is as an actor because he was able to, no matter what was happening in the scene, you can always cut to Matt and he’s alive and loose and present and never forces anything and never does anything false. And it’s so natural that it’s sort of easy to take for granted because he makes it look easy. But what he does, it’s actually quite hard. He does it so well. I have learned from the kid I knew growing up and the young man that I knew and worked with to who he is now—it’s been such a joy, an education, and a treat to appreciate and watch him just become better and better and better at this thing that he devoted his life to and at which he is so very talented.

What was it like to go through this experience together, and be back with him, creating something and bringing this to life together after so many years of friendship?

It reminds me, it reinforces the belief, that this realization I have that I could to some extent dictate the quality of my life really by steering my work toward people I love and people who I admire. And that if you’re really lucky, you get to just feel the joy at work and then you don’t work a day in your life. So when that’s been true, well I say that’s never been more true than it was in this movie where coming to work was clearly the best experience professionally in my life. And it was because of the people I was around, especially Matt, obviously who I love very much, care about him, and would be friends with obviously even if we didn’t have the opportunity and privilege to make films and work together.

It was probably the best reward I guess, that I can think of in a very nebulous world that’s always changing what’s cool or relevant, that as actors, I think people tend to look for concrete totems that they’ve actually put in their time. Because you don’t get the gold watch when you retire. There’s nothing that says, “I was here,” except for the performances that you leave behind and there’s something that says to you, “OK, you’ve made it.” In some ways, you always feel like you are auditioning as a young person, it just leaves you with a sense of that the phone could always stop ringing. And this was, to me, rewarding because I felt like I’ve really been able to put myself in a position to work with my best friend and to feel comfortable and joyful doing that. So it was very personally rewarding

Do you still feel like that the phone could stop ringing after winning Oscars? That’s still a feeling that you have now?

You know? Yes. What I’ve discovered is that the idea that outside approbation or approval is going to sort of fill the place in you that is anxious or wanting or feels like it has something to prove. It doesn’t actually do it, strangely enough. And so that you have these kind of moments that are supposed to create that feeling in you and you find, I think one finds, that it generally doesn’t. It’s not lasting, that the things that last in life are not the totems or trophies or ribbons.

It’s the feeling that there is some sort of permanence or something lasting in what it is that you’ve done and a confidence that you know how to do it. And really for me it’s like what kind of a life do you have? Can you create? My goal was just to be able to say I was a working actor, director, and writer. I did not have to have another job to support myself financially while I tried my hobby. And so, from that standpoint, it was really, really very satisfying. But yes, those things, that’s the great illusion as you think those other things are going to do it for you and they don’t.

There’s always a bigger dream to dream after you get there, there’s always something else you want to do, for sure.

Yeah, there is. And that’s also not the dream. It turns out your dream is about—whatever those moments are, they kind of represent accomplishment, but they don’t feel like it unless you, yourself, I think, feel esteemable. I think it’s common to have imposter syndrome; it’s a constant sort of pressure. What have you done for me lately? What did you do this year? It feels very fleeting. There’s no tenure, there’s no nothing.

It’s just a difficult thing. But what it asks of you is to come to terms with yourself and your life on your own terms honestly. And to be able to do that then you kind of stop needing the other stuff. I want to have the seeds of work, to have the opportunities to work. But I also feel there’s a nice thing to not feel desperate about it because paradoxically, that urge, that urgency, it can inhibit you from doing your best work.

Image via Amazon Studios

Now you have the freedom to do the projects that you really believe in. Seeing you progress into being a director and hearing someone like Viola Davis say that she trusts you as a director. How does it feel to be in this space in your career, and to have these people tell you that you make them feel safe and that they trust you as a director of a film?

Well, I think the highest praise that I can feel genuinely proud of is from people who I respect, who I admire, and who I think are real masters. And my ambition as a director, one of the things that I kind of held onto to as I’ll really have made it, I’ll have done something, if I could have Viola Davis in a movie I directed. That represented a lifelong accomplishment for me and one that I wasn’t sure would ever happen, I feel the same about working with Robert Richardson as a cinematographer and some others.

But Viola was a kind of pinnacle represented to me, the best actor around. And I thought, “Well if that person were in my movie, that would mean that I was really a director.” And the fact that she did the movie and whether or not she did it because Michael Jordan wanted it or because I did, is immaterial [Laughs.] because ultimately she had a good time doing it and I think she’s wonderful. And so at the very least, I do take some pleasure in having not gotten in the way of Viola turning in a magnificent performance. And sometimes as a director, that actually is your job to know when to get out of the way.

There was a lot more humor in the movie than I expected. You told this serious story in a way that was really humorous and really engaging. Was that your goal going in that as important as the story is for the Jordan family, that it was lighthearted and entertaining for viewers?

Yeah, I think my point of view about life and drama and storytelling, I guess, but in particular writing and directing and acting, but I don’t think you can really separate out humor from life. I think humor is the heart of the melon of life. It’s like the best part and it’s present in life whether you’re at the gallows or having a blast. The idea that we kind of silo off, “Well this movie’s a comedy, so it’s funny and this movie is drama, so it isn’t,” always seems strange to me because life is plenty dramatic and those are often the times when we laugh the most.

In fact, like Mozart said about music, a drama, I think, feels like tension and relief to me, and the relief of the laughter and it’s our ability, it’s kind of what makes us humans. Our ability to laugh at what sometimes feels like the cosmic joke of our lives. There’s nothing that makes you like somebody more, be drawn to somebody more than having a good sense of humor. I think it’s the highest form of intelligence. It’s why I love being around Chris Tucker. It’s why Matt, that makes part of why we’re such good friends, is because he makes me laugh. You don’t value anybody more than as a friend, than the person that makes you laugh until you’re in tears. Laughter is not separate from drama or life or anything. It actually happens to be part of it in order for you to feel that experience as fully.

So I wouldn’t be interested in a story that was utterly humorless. Maybe the subject is dark or ironic it would seem this grueling and unpleasant and sort of deliberately obtuse to the nature of life. And so to me humor is always in it, in Live By Night or Gone Baby Gone, there are things I laugh at in those movies because that’s sort of how life is. You have a movie and nobody ever finds anything ironic or whatever it is, it doesn’t feel like a complete, real story to me. I’m very drawn to humor and things that are funny. I get a lot of pleasure and use them a lot.