Summary

• Early career defining role: Fred O'Bannion in Dazed and Confused, key in demystifying filmmaking process for Affleck.
• Breakthrough success: Good Will Hunting, with Affleck awarded the youngest Oscar winner for best Original Screenplay.
• Artistic collaboration: Affleck's work with Kevin Smith, Chasing Amy standout for its deep themes and performances.

Ben Affleck's career has been full of ups and downs, and numerous movies have defined his unique trajectory. While Affleck started as a child actor, he soon made a name for himself as an Academy Award-winning screenwriter, a major blockbuster star, and later the director of a Best Picture-winning film at the Oscars with Argo. While his personal life has fueled as many stories in the tabloids as his acting has in movies, Affleck has continually impressed audiences and critics alike and had one of the most varied careers in Hollywood.

From his earliest film roles, such as the cult classic Dazed and Confused, to later nuanced performances in which he channeled his personal struggles, Affleck has truly done it all in Hollywood. With successful collaborations, such as his creative partnership with Matt Damon, numerous appearances in the work of Kevin Smith, and his equally impressive success as a writer-director, there were many disparate strands to Affleck’s appeal. Affleck has been an action star, a superhero, and a restrained and poignant dramatic actor throughout a turbulent but often inspiring career.

8 Dazed and Confused (1993)

Ben Affleck as Fred O'Bannion

Ben Affleck began professional acting during his childhood as the star of the children’s PBS series The Voyage of Mimi and later gained minor uncredited roles in series such as Buffy the Vampire Slayer. However, before he found his breakout success in Hollywood, Affleck's most notable role came with the release of Richard Linklater’s Dazed and Confused. Affleck played the high school bully Fred O'Bannion in this influential cult classic, which proved just how impactful a more laid-back and artistic style of filmmaking could be.

Affleck credited Dazed and Confused with “demystifying” the filmmaking process for him (via Playboy), as the group of young actors could all contribute their own lines and scene ideas. Linklater stated he cast Affleck in this villainous role because he wanted a likable actor for the part of “a formidable bad guy” (via Daily Beast), as his “big and imposing” demeanor and smart attitude fit the bill perfectly. Linklater’s early self-made success opened the door for Affleck to do the same as he created his own opportunities by developing a creative partnership with his long-time friend and collaborator, Matt Damon.

7 Good Will Hunting (1997)

Ben Affleck as Chuckie Sullivan

A definitive moment in the early part of Ben Affleck’s career came when, at age 25, he became the youngest person to win an Academy Award for Best Original Screenplay for Good Will Hunting, which he co-wrote and co-starred in with Matt Damon. Damon played the lead, Will Hunting, a mathematician genius janitor discovered by a professor at MIT, while Affleck played his loyal best friend Chuckie Sullivan, who saw the incredible potential of his friend’s extraordinary intellect. The nuanced and layered characterizations in Good Will Hunting made it a success and signaled Affleck and Damon as major Hollywood up-and-comers.

The success of Good Will Hunting meant that Affleck was forever an Academy Award winner, which gave him and Damon real momentum in the industry, both as a duo and separately. Good Will Hunting separated Affleck from the average struggling actor, afforded him plenty of early career opportunities, and allowed him to sustain a successful career for decades. With a budget of $10 million (via The Numbers), Good Will Hunting grossed over $225 million worldwide, making it both an artistic and financial smash success for Affleck and Damon.

6 Chasing Amy (1997)

Ben Affleck as Holden McNeil

Another significant collaborator of Ben Affleck’s was the director Kevin Smith, with whom he first worked on Mallrats in 1994 before taking up the lead role of Holden McNeil in perhaps Smith’s most artistically satisfying film, Chasing Amy. As a romantic comedy-drama, in many ways, Chasing Amy was ahead of its time in the way that it addressed sexuality, deconstructed LGBTQ+ relationships, and presented taboo topics not often seen in mainstream cinema, although there’s also the argument that it was misguided in its thematic execution. Either way, Chasing Amy was a definitive film in Affleck’s filmography.

With an interesting storyline and meaningful messaging around love, friendships, and accepting the past, Chasing Amy was a rom-com that strived to be much deeper as it sought to address confusing sexual politics for wayward 20-somethings. Affleck and Smith have continued their working relationship throughout the decades, and he later starred alongside Matt Damon in Dogma and numerous other View Askewniverse movies. As a representation of Affleck and Smith’s longstanding creative collaborations, Chasing Amy was a definitive release in his acclaimed career.

5 Armageddon (1998)

Ben Affleck as A.J. Frost

Throughout the 1990s, Ben Affleck experimented with many different types of movies, from the Best Picture-winning period piece Shakespeare in Love to the sci-fi horror Phantoms, but his real introduction to the world of blockbuster movies came with Armageddon in 1998. As a star-studded action disaster movie starring Bruce Willis and directed by Michael Bay, Armageddon was a turning point as Affleck transformed into a bona fide movie star. Taking in a global gross of over $550 million (via Box Office Mojo), Armageddon was the highest-grossing film of the year worldwide and opened the door to even bigger opportunities for Affleck.

Following the success of Armageddon, Affleck was cast as the lead in Bay’s big-budget romantic war drama Pearl Harbor, which, although derided by critics, was a major success worldwide and brought him even more recognition. Armageddon was the pinnacle of a string of good luck for Affleck, which helped make him one of the most sought-after names in Hollywood. As Affleck’s upward trajectory continued for years unimpeded, it was only a matter of time before things started to go wrong for the young star.

4 Gigli (2003)

Ben Affleck as Larry Gigli

Unfortunately, 2003 was not kind to Ben Affleck, as he found himself in the midst of several professional failures due to the lackluster response to his superhero debut in Daredevil and the sci-fi failure that was Paycheck. However, it was also the year of Affleck’s greatest blunder, Gigli, a romantic crime comedy he starred in opposite Jennifer Lopez, which has often been described as among the worst movies ever. Gigli was also significant due to the highly publicized romantic relationship between Affleck and Lopez, a Hollywood romance story that, for better or worse, has continued to this day.

Gigli signaled a defining box office failure for Affleck, making just $7 million against its $72 million budget (via Box Office Mojo.) This astronomical financial failure meant that Gigli was one of the most expensive box office flops of all time, the after-effects of which significantly impacted the momentum of Affleck’s impressive career up to this point. As the lingering memory of the Gigli fiasco followed Affleck for years, he did not truly recover until he was able to rebrand himself as a writer-director of his own projects with films like Gone Baby Gone and The Town.

3 Argo (2012)

Ben Affleck as Tony Mendez

After carving out a new identity as a director of real talent, Ben Affleck achieved a level of success previously unseen in his entire career with the release of Argo in 2012. As the Best Picture winner at the Academy Awards, Argo, which was directed by and starred Affleck, was a deception of C.I.A. operative Tony Mendez’s covert rescue mission, ‘Canadian Caper,’ where six U.S. diplomats were rescued from Tehran, Iran. As a mission done under the guise of a fake science fiction film, Argo brought together Hollywood’s love of storytelling with real-life espionage heroism.

While declassified information has proved some aspects of Argo were depicted wrongly, and the film received criticism for its historical inaccuracies, it still received widespread acclaim and accolades. As a tense, exciting, and often comic story, Argo's success embodied Affleck truly overcoming his past failures and box office bombs, as it received multiple esteemed awards. Argo was top-tier filmmaking and immediately silenced those who doubted Affleck’s reputation as a force to be reckoned with both in front of and behind the camera.

2 Batman V Superman: Dawn of Justice (2016)

Ben Affleck as Bruce Wayne / Batman

Thirteen years after the failure of Ben Affleck’s last superhero project, Daredevil, he returned to the genre after being controversially cast as Bruce Wayne/Batman in Zack Synder’s Batman v Superman: Dawn of Justice. While Batman v Superman underperformed at the box office and was badly received by critics, Affleck’s portrayal of the Caped Crusader was one of the few things people unanimously agreed was done well. Dubbed ‘Batfleck’ by the press, Affleck played an older, more jaded version of Bruce Wayne that felt poignant and unique among cinematic portrayals of the vigilante crime fighter.

Although Batman v Superman was part of the DC Extended Universe and plans had been made for an Affleck-led Batman solo movie, these plans never came to fruition, and his tenure as Bruce Wayne felt like a bittersweet, noble failure. While Affleck continued to play the character in further movies like Suicide Squad and Justice League, following the release of The Batman starring Robert Pattinson, it looked like all chances of a solo outing for ‘Batfleck’ were no more. This sad development was littered with wasted opportunities and endless what-ifs about Affleck’s Batman.

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1 The Way Back (2020)

Ben Affleck as Jack Cunningham

Ben Affleck’s later career included esteemed roles in the thrillers Gone Girl and The ant, but the performance that hit closest to home was in the excellent sports drama The Way Back. With a story about an alcoholic construction worker who became head coach of the basketball team at the high school where he was once a star player, The Way Back had extra resonance because of how well it related to Affleck’s own life story and struggles with addiction. With a highly nuanced portrayal, it felt like Affleck put a lifetime of experience into the part of Jack Cunningham.

As an of anguish, self-destruction, and the path toward redemption, The Way Back was produced in the wake of Affleck’s alcohol relapse and was shot shortly after he left rehab (via Inquirer.) As one of the best performances in Affleck’s entire career, The Way Back felt personal and poignant, and it was impossible as a viewer not to relate the power of his portrayal to similarities between his struggles. As an actor who experienced plenty of ups and downs, this late-career highlight showed that, no matter how much he faltered, Ben Affleck always found the way back.

Source: Playboy, Daily Beast, The Numbers, Box Office Mojo, Inquirer