Some bets are risky and other bets are plain stupid. Betting against Ben Affleck is a fools game. The actor/director/writer/producer (and now studio head) has had a career that has taken a second life and then a second life after that. Turning to directing films in 2007 with the crime thriller “Gone Baby Gone” showed this Boston obsessed man knew how to capture his hometown while also keeping the adult drama alive at a time when it was heading out. Following it up with 2010’a “The Town” and the majorly successful Argo, (where he was egregiously snubbed of a best director academy nomination) these films continued to show Affleck’s talent for dramas about men with bigger sights on their mind regardless of their own destruction keeping them back. Now Affleck is back in the director’s chair and brought his best friend along. Matt Damon and Ben Affleck were just recently on screen together with “The Last duel” but this time around they take a much different story than that but one the two men are very familiar with. AIR COURTING A LEGEND may be the story of how Nike won over Michael Jordan one fated weekend, but it is also a tremendous portrait of legacy and how artists are the ones to truly create it. It is also a massive crowd pleaser fitting into the sports drama of those in charge fighting against the norm. AIR also is smart and never tries to be the Michael Jordan story, you know that story, and even if you don’t Affleck knows his team (mostly consisting of white men) are not the people to tell it. What Affleck and Damon (and their new company of Artist Equity) do what to tell is this tremendous story of a man knowing a legend when he sees one but even more sure realizing that legends become who they are because of the mothers standing by their side, and no fancy shoe can compete with a determined mother.

Sonny Vaccaro (Damon) is a gambler. Working for Nike as their ‘basketball guru” he spends his days traveling to see potential high school players that could change the game forever. But that doesn’t stop him from his reoccurring stopover in Vegas to hit the tables. Sonny seems to be winning at the casino but is still struggling to find that next big name. His job is harder when given the fact that Nike is losing the sneaker game to Converse and Adidas. Yes imagine a time (1984 to be exact) where Nike was not only struggling to keep up in the sneaker war, but their best asset was giving shoes to the elderly generation for they could go for their daily mall walks. Vaccaro might be a basketball guru but he needs to learn a little bit more on the changing culture being defined by shoes. His co-worker Howard White (a tremendous Chris Tucker) even says he only wears Adidas and it’s the shoe of the moment as its about to be featured in a Run DMC music video (again its 1984 people). Damon as Vaccaro is in such a comfort zone but never just settles in the role, he amps up the everyman vibe with he same charisma and danger that Damon showed back in ‘The Talented Mr. Ripley.” Damon also gets to show that some of his best work is done bouncing off other performers. This includes a devious Chris Messina as Michael Jordan’s agent David Falk, and of course his best friend Affleck who also stars as Nike founder Phil Knight. Vaccaro knows profit wise Nike can’t win over Jordan, but he’s advised that the mothers run the players home and no women is more in charge than Deloris Jordan (Viola Davis). A little behind the scenes tidbit, but Michael Jordan who Affleck reached out to to get the story right had one major request, Viola Davis must play his mother. A tall order, but a necessary one as Davis is not just one of our greatest actors of all time, she brings such a severity to Deloris that is rooted in nothing but love for her son and understanding of the real world and how Black men have been abused for decades in this industry. Deloris knows her son isn’t interested in Nike’s offer of any kind, but Davis is able to have such subtle expressions that she speaks a thousand words during a scene where she and Sonny first meet that says, you seem different but you’re going to have to work like hell to win over me and my family. A powerful moment in a film full of them.

AIR is the kind of film that could have been riddled in cheap nostalgia and while there are several big moments that will have anyone familiar with Jordan’s story cheering, Affleck and screenwriter Alex Convery knows never to belittle the moments. When Sonny reaches out to creative director Peter Moore (Matthew Maher) you can feel that that exists right before a monumental shift start to rev up. Maher as Peter Moore may be the film’s secret weapon, a character actor who brings the piece of heart of the film that exists to tell us that while we may only know Air Jordan with the player, there was also once artists behind everything helping create something that will stand long after they are gone. But in doing so also creates a level of responsibility that touches every worker. Affleck and Damon, who also worked on the script are clearly throwing in a needed plug for their new company Artist equity where to sum it up gives money back to the creative team, but also causes them to have more stakes in the game. Vaccaro in the movie knows this has to happen and believes in Jordan and much like the film is spearheaded by a director who believes in his team of creatives and the collaboration pays off. To the masses AIR may just be winning escapism but much like Nike it is a new attempt to shake up an industry that has built itself on strangling creatives.  

If AIR is a story of creatives that Deloris and the Jordan family are the audience that needs to be convinced. Affleck knows the world of movies and theater going is dominated by tentpole franchises (hell the man has been the face of several) but his directing finds its true comfortability in the telling of stories about adults living in a world where giant corporations or bureaus run the world. AIR is a plea and a reminder that not only do these stories matter, but they will hold a place in history and will always go through a process of being cheered for and also rejected. The more Sonny tries to win over Deloris and Michael, the more that realization comes into play. Sonny knows Michael will be a name synonymous with greatness but no great thing is beloved forever. The shoe will represent every time Michael flies as well as every time he falls. AIR stands by that same mentality. We need these stories, and we need these films, to come back to when we fly and when we fall. Affleck is making a big pitch to us with AIR, but this one is a no brainer. Take the leap.




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