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Ben Affleck's Best Movie Roles To Date

Ben Affleck's acting career has seen some highs and lows over the years. After establishing himself in lightweight comedies, his career took a turn when he co-wrote and appeared in "Good Will Hunting" beside Matt Damon. The two penned the script together, which went on to win a Golden Globe and Academy Award for Best Original Screenplay. With this feature, they hit the jackpot and became A-list actors in Hollywood. By the end of the '90s, Affleck earned a leading man status and starred in several lucrative blockbusters.

In 2003, though, Affleck's career changed for the worse due to his over-exposed relationship with Jennifer Lopez. He was in movies that were doomed from the beginning and took on roles that weren't right for him. As a consequence, he was almost completely written off as a reliable lead actor. Considering the low points he hit in those years, it's impressive that he managed to find his way back to success.

From 2006, Affleck picked parts that were much more suited for his talent. In 2007, he made his debut as a director, which reinvigorated his acting. He chose darker, more complex, and subtle characters to play, creating a chance to reveal a depth we'd never seen from him before. Although it wasn't all uphill from there — he still appeared in a few poor films — his last three roles found him at his absolute best. Riding that wave, we gathered his most acclaimed ones to date.

Chuckie Sullivan (Good Will Hunting)

The movie that brought Ben Affleck worldwide fame remains one of his top performances. Chuckie Sullivan — the working-class Bostonian and close friend of Will Hunting (Matt Damon) — is a natural boaster. He's broke and poorly educated, but he's inherently amusing, charming, and loyal to his friends. Sure, Will is the absolute hero of Gus Van Sant's classic, but without Chuckie, the climax wouldn't pack such an emotional punch. And Affleck is very aware of his character's crucial importance to the story.

Although he was born in Berkeley, California, Affleck can't deny his Massachusetts roots, which are the pillars of "Good Will Hunting's" authenticity. His accent, the tough guy act, and the foul mouthing perfectly capture Chuckie's personality. He's a low-life nobody who works construction, drinks a lot, and smokes a pack of cigarettes a day. But he won't let his best friend's exceptional talent go to waste the same way just because Will is too afraid to face the possibilities that could bring him a better future. Among other things, their camaraderie and devotion to each other are what makes the 1997 drama so remarkable.

Doug MacRay (The Town)

The heist thriller "The Town" is Ben Affleck's follow-up to his directorial debut, "Gone Baby Gone." This time, however, he cast himself in the leading role of Doug MacRay, the leader of a proficient group of thieves. The movie takes place in Boston and follows a gang of criminals robbing banks and trying to get away with it.

There's a particular efficiency and sincerity whenever Affleck plays a character from Massachusetts. Naturally, when he represents a Bostonian, he's much more involved on a personal level. The way he portrays MacRay and his relationship with his crew have an empathetic and respectable quality. He wants a way out of this life, but he knows that would also mean losing the people he considers his family. It's a moral dilemma wrapped in some toxic masculinity that puts pressure on him right from the beginning. Yet he's able to convey these feelings while keeping the character genuine throughout. It's one of his best roles because his personal involvement and dedication to the project shine through compellingly.

Holden McNeil (Chasing Amy)

After briefly working together with Ben Affleck in the mid-'90s, Kevin Smith decided to cast him in the leading role of his third movie, "Chasing Amy." As Holden McNeil, he was tasked with a trickier part than the ones he previously played in Smith's "Clerks" and "Mallrats." He portrays a comic book artist who falls in love with a girl who happens to be gay. At first, the writer-director approaches the subject from a comedy angle, but the plot quickly turns into a romantic drama loaded with questions and complicated feelings about gender and sexuality. Holden is a pretty simple guy who finds himself in a difficult situation where expressing and dealing with love turns out to be a tough challenge.

Affleck's performance here is full of tenderness and vulnerability. His emotionally charged monologues and dialogues convey the insecurity and inadequacy his character goes through while trying to do the right thing. Whatever he does — whether good or bad — he always makes us believe that he acts on the impulses and emotions he feels to be true. Smith's screenplay was ahead of its time, but Affleck and his co-stars managed to hit the right notes and bring authenticity to the portrayal of these people, who face something profoundly unusual they have little experience with.

Pierre d'Alençon (The Last Duel)

After "Good Will Hunting," it took over 20 years for Ben Affleck and Matt Damon to work together on another script again and be in the movie as lead and supporting actors. It was worth the wait, though: their collaboration in Ridley Scott's medieval historical drama was one of the bangers of 2021. Unfortunately, the feature didn't perform well at the box office despite wide critical acclaim and high praise from viewers. Yet that doesn't take away from its quality and the fantastic performances all around.

Although Affleck's Pierre d'Alençon is a supporting role, some of the most memorable and funniest moments of the film belong to him. He acts with ease, conveying a cruel and arrogant hedonist who abuses his powers as a count — defending or attacking whoever he wants and never apologizing for anything. He embraces the role to play such an awful human being and proves that he's got the skill to depict a spiteful yet entertaining character. What he delivers here definitely adds to his acting repertoire.

Uncle Charlie (The Tender Bar)

Ben Affleck's latest part in George Clooney's "The Tender Bar" is a welcome delight. He's the main reason the film is somewhat amusing and enjoyable. The script — based on J.R. Moehringer's memoir — might be a little empty and dull, but Uncle Charlie is the highlight of this bittersweet tale.

He's the father figure in the protagonist's life after his real dad took off and left him and his mother when he was little. The plot is set in the 1970s, where Charlie runs a local bar called The Dickens in Long Island. He's the kind of street-smart, self-taught person we'd all love to have growing up. He knows everyone on a first-name basis, talks in a slick way, and has the sort of mindset that entails a lot of hard-earned wisdom. But most importantly, he is a happy and satisfied man who made peace with a modest life — he has no regrets about what he has become. There's an appeal to a character who hasn't achieved anything remarkable yet is totally fine with that. Affleck immerses himself in this role, using his smooth charisma to make us like him in an instant. Despite not being the hero of the story, he's the one we'll remember when everything else fades away in time.

Jack Cunningham (The Way Back)

It's no secret that Ben Affleck experienced addiction multiple times during his career. His drinking caused a lot of trouble for him over the years, and he went to rehab multiple times. In Gavin O'Connor's 2020 drama, "The Way Back," Affleck taps into that experience. He plays Jack Cunningham, a middle-aged, has-been high school basketball star who tries to drown his battered soul in alcohol. He's a divorced ironworker, living each day in misery when he gets one last shot at redemption when Father Divine (John Aylward) offers him a job at his former Catholic high school coaching their basketball team. He takes the position and slowly begins to emerge from the pits of hell he exiled himself to a long while ago.

Affleck gives a performance that's devoid of any exaggeration or dramatic outbursts — he stays restrained until the finale. It's only when Jack starts to awake from his depression and self-loathing and finds a new reason to live again that Affleck brings the type of intensity and vital spirit we know him for. It's not a revelation — we're aware of what he can do when he's fully committed and in form — but it's an effective way to prove that he still has the spark that can make him outstanding in such a quiet role.

Nick Dunne (Gone Girl)

David Fincher's 2014 psychological thriller "Gone Girl" became a modern classic for a reason. It's a complex, dark portrayal of a twisted marriage filled with unthinkable secrets and deadly insanity. In it, Ben Affleck plays Nick Dunne, a bar owner whose wife, Amy (Rosamund Pike), goes missing. The shocking news turns into a media sensation as speculations begin to suggest that Dunne is a sociopath who murdered his own wife. Of course, since this is a Fincher crime epic — based on Gillian Flynn's bestseller novel — the truth is much more complicated.

Affleck's casting for the lead role was a genius move. He's the tall, handsome guy that almost everybody finds amusing. The audience knows him long enough to expect that quality whenever he appears on the screen. However, the fact that nice guys are sometimes rapists and vicious murderers is also at play. Affleck skilfully goes along with this duplicity to keep up the thrilling suspense around the question of whether he's guilty or innocent in the case of Amy's disappearance. But as the story unfolds, we learn that he's not really the person everyone expects him to be. Regardless, Affleck showcases an unusual performance here, which catches us by surprise in the most rewarding way.

Bobby Walker (The Company Men)

John Wells' 2010 film "The Company Men" is a convincing portrayal of the recession and its consequences on white-collar America. Bobby Walker (Ben Affleck) is among those many workers who fall victim to the downsizing of a shipbuilding corporation called GTX. After getting fired, his dreamlike life — which includes a good marriage, two kids, a prestige golf club membership, daily lunches at expensive restaurants, and a Porsche Boxster in front of his huge six-figure house — gradually falls apart. He loses nearly everything. Unable to find another corporate job that matches his skills and the salary he deserves, he ends up working construction for his brother-in-law, who he loathes. Wells' drama has no disillusions about how quickly a successful man can hit rock bottom in the United States.

Affleck doesn't aim for our pity but genuine sympathy. Among such veterans as Tommy Lee Jones, Kevin Costner, and Chris Cooper, he can't rise to the same level as these legendary actors, but he tries hard enough. By the end, his efforts pay off as he transforms from a slightly arrogant businessman into a likable father and husband who humbles himself to work a job that's beneath him. He does whatever he has to in order to save his family and make ends meet in the most challenging times.

Christian Wolff (The Accountant)

"The Accountant" is another double bill of director Gavin O'Connor and Ben Affleck. In the 2016 film, the actor plays Chris Wolff, a highly functioning autistic and forensic accountant who's uncooking the books for some of the most dangerous criminal and terrorist organizations in the world. When he's hired to audit a firm called Living Robotics, he discovers that $61 million was embezzled over the years. Meanwhile, Ray King (J.K. Simmons), the director of the Financial Crimes Enforcement Network, leads an investigation to reveal Wolff's secret identity and his involvement in the murders of nine members of the Gambino crime family. Eventually, Wolff is forced to go on a run — with authorities and hitmen breathing down his neck — to find a way out of this life-threatening chaos he put himself in.

Despite some plot inconsistencies, Affleck's portrayal of a highly functioning autistic is accurate and believable. He remains emotionally controlled and thoroughly methodical throughout. Although, in the second half, the film's focus shifts to brutal and nail-biting action sequences, which somewhat push the characters out of the spotlight. Nevertheless, Affleck maintains a strong presence that culminates in a dramatic and moving twist in the finale. Chris Wolff is indeed the type of character that we rarely see him take on, and it's a real treat to watch him perform out of his comfort zone.

Jim Young (Boiler Room)

In Ben Younger's 2000 feature debut, "Boiler Room," Ben Affleck only has a supporting role, but his character lays down the foundation of the entire movie. He plays Jim Young, a 27-year-old millionaire and the co-founder of the brokerage firm J.T. Marlin. In an early scene, he walks into a conference room full of young men fresh out of college who are hungry for success and money. Young delivers a motivational speech, telling everyone how rich he became in a few years. He lists all the things he acquired thanks to J.T. Marlin and says that everyone who gets hired will be a millionaire within three years.

Without question, Affleck's straightforward and potent monologue is the greatest part of the movie. He depicts this character with a smug smile on his face and swag that screams confidence. You believe every word he says even if, in the back of your mind, you have a suspicion that all of this sounds too good to be true. But his delivery is so impressive that you fall for it just like the rest of the fellas in the office. Clearly, Affleck's got a knack for bringing this type of complacent and showy character to life on screen, and he demonstrates it perfectly in "Boiler Room."

Stephen Collins (State of Play)

Kevin Macdonald's 2009 political thriller "State of Play" is based on a British television serial of the same name. In it, Affleck is Congressman Stephen Collins, a military veteran who learns that a female member of his staff was killed by a Washington Metro train. The news hits him hard since he was having an affair with the young woman. When police suggest it was suicide, Collins disagrees and turns to his old college roommate, Cal (Russell Crowe), a Washington Globe investigative reporter. Cal starts to look for clues and people who might've been associated with the dead woman to find out what really happened to her. But later on, the pair discover that this case is a lot more intricate and threatening than they could've imagined.

At first, Affleck's part doesn't seem the type that can easily earn sympathy from the viewers. Yet his agenda and motive to uncover a company named PointCorp that gains billions of dollars from mercenary activities in the Middle East is something we can stand behind and support. He conveys this public figure with fierce vulnerability, despite knowing that he's far from a good human being. Ultimately, this complexity is what makes the performance one of his most intriguing roles.

Gavin Banek (Changing Lanes)

Roger Michell's 2002 thriller "Changing Lanes" is about two selfish men who meet at the worst time in the worst way possible. One of them is a lawyer, Gavin (Ben Affleck), who's about to close his biggest case, while the other one, Doyle (Samuel L. Jackson), is a recovering alcoholic in the middle of a divorce. When Gavin crashes his car into Doyle's, their lives begins spiraling out of control. Instead of helping each other out by doing the right thing, they start a pity war that leads to the most miserable day of their lives.

As the arrogant and wealthy lawyer, Affleck's casting is fitting. As Gavin, he goes through a moral process to rediscover the humanity in himself. He tries to cheat and lie his way into what he wants and justify an unethical decision he made but struggles to admit it. The chemistry between the two actors is excellent, and they bring the most out of each other. After 20 years, "Changing Lanes" still holds up due to the powerful duo that makes this feature one of Affleck's finest performances.

Tony Mendez (Argo)

"Argo," Ben Affleck's third film as a director, was a financial and critical triumph. It was nominated for seven Academy Awards and won three for Best Picture, Best Adapted Screenplay, and Best Achievement in Film Editing. He cast himself in the lead role of Tony Mendez, who was an American technical operations officer working for the CIA. Mendez led the rescue of six U.S. diplomats who were held hostage in Iran at the end of the 1970s. The feature is loosely based on his memoir and depicts how he organized the shooting of a fake science-fiction film to create an opportunity to get the hostages out of enemy territory.

It's undoubtedly one of Affleck's most significant roles and brought him well-deserved recognition. In an interview with Jake's Takes, the actor-director explained, "One thing that I was pleased about when it ["Argo"] started to play more broadly was that I felt good because I had a movie that was about something more than me." He continued, "It was about this guy, a real hero, and about the work done in our intelligence community. What they go through, and what State Department employees do. I had relevance to real relevance. So, I was extremely relieved and encouraged that people would get to see this, and I hoped I was right that it would spark some debate conversation." Thus "Argo" isn't just one of Affleck's top performances, but it's one of the most important pictures he's ever made.