Affleck's first major role as a Hollywood leading man, in Armageddon, the actor stars alongside Bruce Willis as they set out to stop a giant asteroid from colliding with Earth. The film follows Harry Stamper (Willis) as he is enlisted to recruit a team of blue-collar workers who are tasked by NASA be sent into space and drill into the asteroid (obviously). In the hopes of saving the world from impending doom, Harry includes A.J. (Affleck) in his team, who also happens to be the love interest of his daughter, Grace.

Cue Aerosmith's I Don't Want to Miss a Thing.

Despite unfavourable critic reviews, the film received international box-office success, and become the highest-grossing film of 1998 worldwide. 

Stepping back from the role of a leading man, Affleck took a surprising supporting part in the 1998 hit Shakespeare in Love, starring alongside his then-girlfriend Gwyneth Paltrow.

Taking the role of an arrogant English actor in the period romantic comedy, the film depicts a fictional love affair involving playwright William Shakespeare (Joseph Fiennes) and Viola de Lesseps (Gwyneth Paltrow) while Shakespeare was writing Romeo and Juliet.

After several smaller roles, Affleck teamed up with director Michael Bay (Armageddon) once more in the blockbuster, Pearl Harbor. Alongside Affleck, the film stars Kate Beckinsale and Josh Hartnett as it presents a heavily fictionalised version of the Japanese attack on Pearl Harbor on December 7, 1941, focusing on a love story set amid the lead up to the attack and its aftermath.

Much like Armageddon, the film received generally negative reviews from critics, though was a box office success, earning $59 million in its opening weekend and nearly $450 million worldwide. If you like romance films, that are loosely based on historical events, it's still worth a watch if you have a spare three hours.

A departure from the cheesy Blockbusters that Affleck was now known for, in 2002, he starred in the American drama thriller Changing Lanes. 

The film follows a successful, young Wall Street lawyer (Affleck) who accidentally crashes his car into a vehicle driven by a middle-aged, recovering alcoholic insurance salesman (Samuel L Jackson). After the lawyer leaves the scene of the accident, the two men try to get back at each other, engaging in a variety of immoral and illegal actions that end up having a major impact on each man's life. 

Both a critical and box office success, Affleck later cited director Roger Michell as someone he learned from in his own role as a director down the line.

Although from 2007 Affleck primarily focused on his budding career as a director, he did take several roles in big name movies during this time. One such film is the 2009 romantic comedy He’s Just Not That Into You.

Following the lives and loves of nine different characters, the ensemble cast is made up of stars including Drew Barrymore, Bradley Cooper and Scarlett Johansson, with Affleck starring directly alongside Jennifer Anniston. Though receiving mixed reviews, the film still grossed US$27,785,487 during its opening weekend, and over US$178,866,158 worldwide. If you're a lover of rom-coms, it's certainly one to add to the list.

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Not only does Affleck star and director in this 2010 crime thriller, but he also co-wrote the script. 

Set in the neighbourhood of Charlestown, Boston, The Town follows a group of lifelong friends, including Douglas "Doug" MacRay (Affleck) and James "Jem" Coughlin (Jeremy Renner). The plot unfolds as the group commit a bank robbery and Affleck's character begins a romance with released hostage Claire Keesey (Rebecca Hall) behind his friend's back.

The tense and gritty plot was praised by critics, with Affleck gaining acclaim for his work as a serious director.

A second film which Affleck both directed and starred in, Argo tells the story of CIA operative Tony Mendez (Affleck) as he led the rescue of six U.S. diplomats from Tehran, Iran, under the guise of filming a science fiction film during the 1979–1981 Iran hostage crisis.

Along with seven nominations at the 85th Academy Awards––three of which it won––the film also earned five Golden Globe Award nominations, as well as winning Best Film, Best Editing and Best Director at the 66th British Academy Film Awards.

Based on the 2012 Gillian Flynn novel of the same name, Gone Girl follows the events surrounding Nick Dunne (Ben Affleck), who becomes the prime suspect in the sudden disappearance of his wife Amy (Rosamund Pike). 

Like the book––which was a New York Times Best Seller––the film was both a critical and commercial success, grossing US$369 million on a budget of US$61 million, becoming director David Fincher's highest-grossing film. It also received several major award nominations.

One of Affleck's most recent works, sports drama The Way Back was released in March 2020. Shown for only two weeks in theatres due to the emergence of the Covid-19 pandemic, the film was also made available for audiences to view-on-demand at home.

The film follows an alcoholic construction worker who is recruited to become head coach of the basketball team at the high school he used to attend, with Affleck taking the lead role. The actor was widely praised for his performance, with the theme itself hitting close to home as the movie was shot in the days after he left rehab for his own alcohol addiction relapse.

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