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The Career Paths of Matt Damon and Ben Affleck After Good Will Hunting

Matt Damon is currently starring in the #1 movie in America, "The Bourne Ultimatum." Ben Affleck hasn't starred in the #1 box office movie in over four years when "Daredevil" opened.

It was ten years ago the two up and coming young actors, fed up with the lack of strong roles being offered to them, decided to write a screenplay of their own to act in. The hope was the two would get better offers for better roles in better films. The result was "Good Will Hunting" and it made Damon and Affleck stars while also winning them an Academy Award for their screenplay (Damon was also nominated for Best Actor).

It couldn't have come at a better time for the two young actors. Affleck was best known for a small role in the 1993 cult hit "Dazed and Confused" and for his starring role in the indie film "Chasing Amy," Kevin (Clerks) Smith's critically acclaimed but little seen romantic comedy about a man who falls hopelessly in love with a lesbian cartoonist. Damon had small roles in such films as "Mystic Pizza," "Courage Under Fire," and "Chasing Amy." Just prior to Hunting, Damon landed a lead role for Francis Ford Coppola in the adaptation of John Grisham's "The Rainmaker." It did not do well at the box office.

Once "Good Will Hunting" broke onto the scene the door opened wide for Affleck and Damon and it is curious to see the paths they have taken. One has become an acclaimed multi-nominated actor in successful films while the other has taken on roles in films more famous for their effects and disappointing box office totals.

Let's take a post-Good Will Hunting look at the careers of Matt Damon and Ben Affleck.

Matt Damon's career took a nose dive for several years after winning the Oscar. His first role was the important title role in Steven Spielberg's war masterpiece "Saving Private Ryan." Damon doesn't appear until almost two hours into the nearly three hour movie but his role is the pivotal one of the film and he pulls it off with comfortable ease. Next up he co-starred with Edward Norton as boyhood pals and addicted gamblers in "Rounders," a film that has become a huge cult favorite, especially with the rise in popularity of poker. In its initial release it was a mild hit.

In 1999 Damon took on a supporting role (with Affleck) for pal Kevin Smith in "Dogma." Later that year he would play the title role in "The Talented Mr. Ripley," as a murdering con man. Damon received his second Academy Award nomination for Best Actor. Despite this the film was a disappointment at the box office.

In 2000 Damon took roles in three important films, Robert Redford's "The Legend of Bagger Vance," Gus Van Sant's "Finding Forrester" and Billy Bob Thornton's "All The Pretty Horses." All three received mixed to poor critical response and all three were huge box office flops. In 2001 Damon did appear in the hit "Oceans 11" but was not credited with much of the success with co-stars George Clooney and Brad Pitt looming in the spotlight.

2002 was an important year for Damon. The offers were starting to dwindle so he decided to write another movie for Hunting director Gus Van Sant. This time Damon wrote with Ben Affleck's younger brother Casey and created the drama "Gerry," about two young men who get lost in the desert and walk and talk as they try to reach civilization. The film received very mixed reviews but was a dud at the box office.

Then Jason Bourne came into Damon's life. "The Bourne Identity" came to Damon at a time when he had all but figured his career, which was on the ropes, was over. Everything changed for Damon when this film became a smash hit. Damon then made an interesting choice by appearing alongside Greg Kinnear as Siamese twins in the Farrelly Brothers 1993 comedy "Stuck On You," which was a box office flop. Small roles in 2004's "Euro Trip" and "Jersey Girl" did nothing for his career and then Jason Bourne came back into his life.

"The Bourne Supremacy" proved to be another strong box office hit and a franchise seemed inevitable. Later that year Damon scored another hit in "Oceans Twelve," despite consensus that the movie was the usual lesser effort sequel.

In 2005 Damon appeared in director Terry Gilliam's little seen "The Brothers Grimm" despite some strong critical reviews. Later that year he had a featured role in the critically acclaimed "Syriana," a box office hit. Damon came on strong in 2020 with a villainous role in Martin Scorsese's Academy Award winning film "The Departed" and the lead role for director Robert DeNiro in the epic drama "The Good Shepherd." Both films did well critically but only the former was a big hit. The latter was a disappointment though Damon garnered strong notices for his performance. This year Damon is currently appearing in two more hits, both of them the third in the series, "Oceans Thirteen" and "The Bourne Ultimatum."

On the other hand, Ben Affleck's career got off to a fast start post-Hunting. After starring in the unfortunate horror film "Phantoms," Affleck had a major role in one of 1998's summer blockbusters, "Armageddon." That same year he had a small role in the Academy Award winning Best Picture, "Shakespeare In Love." He then took small roles in three little seen films, "200 Cigarettes," "Dogma" and "Boiler Room." He then starred in three consecutive box office flops, "Forces of Nature," "Bounce" and "Reindeer Games."

In 2001 Affleck starred in "Pearl Harbor," the summer war epic that received some of the worst reviews a movie could get but still managed to make almost $200 million domestically. After a small role in "Jay and Silent Bob Strike Back" Affleck starred in the critically acclaimed but box office disappointment "Changing Lanes." He then took over the role of Jack Ryan from Alec Baldwin and Harrison Ford for an adaptation of Tom Clancy's "The Sum of All Fears," a box office hit.

It was around this time that Jennifer Lopez came into Affleck's life and soon the country was inundated with stories in the press about the two of them ad nauseum. In early 2003 Affleck starred in his last box office hit, "Daredevil." Later that year Affleck and Lopez teamed up for a comedy/thriller, "Gigli" (pronounced Gee-Lee), which would become one of the biggest flops of this decade. While some blamed the film's failure on the script, most believe that was just fuel to add to the "Bennifer" fire, something which the public had quickly sickened of. Later that year Affleck starred in the Christmas release "Paycheck," and most believed he was in it just for that. What few people saw it were reportedly laughing at each screening.

In 2004 Affleck and Lopez split but the public would have to endure another project from the two called "Jersey Girl," from director Kevin Smith. Fearing the "Bennifer" backlash would hurt his movie, Smith came out and announced that Lopez had a small role and even revealed she dies barely 15 minutes into it. They ploy did not work however and the film was another flop. Later that year Affleck starred in one of the worst comedies of the decade, "Surviving Christmas," a film so bad that co-star James (The Sopranos) Gandolfini told the press he was shocked the film ever saw the light of day. This film was also known as one where the film crew came to Chicago to shoot in January and was shocked at how cold it was. After only two days they picked up stakes and moved to Toronto. I wonder what kind of weather they were expecting in January in Chicago?

In 2020 Affleck starred in "Man About Town," a film that is evidently so bad, so much worse then "Surviving Christmas," it wasn't even given a theatrical release and went straight to DVD. Affleck also had small roles in "Clerks II" and "Smokin Aces," neither of which did much business at the box office. Affleck did bounce back with critics with his Golden Globe nominated performance as actor George Reeves in "Hollywoodland." The film, however, was a huge box office disappointment and this is sighted as a main reason as to why Affleck was not nominated for an Academy Award.

This October Affleck is going behind the camera as co-writer and director of "Gone Baby Gone," based on the novel by Dennis (Mystic River) Lehane. Perhaps Affleck will find success in a new medium. As of now he has no commitments to act in anything so if he fails perhaps Matt Damon will call him and the two can write another project together. If not perhaps Affleck can make an appearance if there is a fourth Bourne film.