The Transformation Of Ben Affleck From 20 To 48 Years Old

Ben Affleck may be back in the headlines these days, thanks to him hanging out with ex-fiance Jennifer Lopez, but the actor never appears to be too far from the spotlight. Since Affleck was a child, it seems he was destined for Hollywood stardom. You could say the "Gone Girl" star has been steadily working as an actor since age 7, when he appeared on screen in the 1981 film "The Dark End of the Street."

Affleck continued to act while going to school, and even pursued work after high school. Yet, the actor's first memorable role came at age 20, when he played school bully Fred O'Bannion in "Dazed and Confused." The film's director Richard Linklater recalled, "It tweaked Ben out because he was the only (jerk) in the film," adding, "but he had this kind of gleeful fun with it."

Affleck continued through the '90s with another notable bully role, this time in friend Kevin Smith's comedy "Mallrats." The actor expressed what that was like to Backstage, saying, "Part of me was like, 'God, am I going to be relegated to throwing people into their lockers for the rest of my career?'" Yet of course that didn't happen, starting with Smith casting him again, but this time as a romantic lead in "Chasing Amy."

After that, it was clear to even Affleck that his star was rising. He remembered, "For the first time, people stopped me on the street to say they saw the movie, and it was the most amazing experience."

Good Will Hunting marked a turning point for Affleck at age 25

Ben Affleck's career took a major turn for the better in 1997 when he co-wrote and acted in "Good Will Hunting," alongside his longtime pal Matt Damon. Affleck recalled writing the script to Boston Magazine, saying, "Matt said, 'Look, will you help me write this? I'm not sure what it is or where to go.' So we started writing it sort of back and forth."

The two not only wrote the film, but then starred in it. Hollywood was clearly impressed. "Good Will Hunting" not only grossed $225.9 million, but earned nine Academy Award nominations, making Affleck the youngest writer to win the Oscar for Best Screenplay at age 25.

After the film's release, Affleck made a name for himself as one of the hottest rising stars. The "Justice League" actor told Parade, "It was a dreamlike time for me from December 1997 to March of '98. Before that, I was basically unknown. Then, bang! The starting gun fired, and everybody just started running." He continued, "It was learn-on-the-job. And there were more opportunities for work than I had time to do them."

The opportunities did continue to come in for Affleck, making him an official leading man.

Ben Affleck became a leading man with a leading lady

Following the success of "Good Will Hunting," Ben Affleck began landing leading role after role in several big projects. The first notable one was in the doomsday action flick "Armageddon." The role proved that Affleck had what it took to be a big action star. While the film was a commercial success, it appears Affleck doesn't necessarily look back too fondly, in terms of what kinds of movies he wants to make. According to MovieWeb, the actor even recently said, "I'm just looking to do stuff that is personally rewarding. I think my 'Armageddon' days are behind me."

During the late '90s to early 2000s, Affleck did go on to make more blockbuster action movies, including "Reindeer Games" in 2000 and "Pearl Harbor" in 2001. But Affleck was still able to wow critics, especially with his supporting role in the 1998 period comedy, "Shakespeare in Love." At the time, Affleck was dating co-star Gwyneth Paltrow.

Paltrow and Affleck were the "it couple" while they dated between 1997 to 2000, but it appears the two did not end on very good terms. Even while they were dating, Paltrow admitted that she knew not to marry him and described his perfect girl on "Good Morning America" as "any sort of stripper at Scores" or "anyone that serves cold beer in a bikini." Paltrow later explained to Howard Stern that "he wasn't in a good place in his life to have a girlfriend."

Ben Affleck becomes half of 'Bennifer' at age 30

Gwyneth Paltrow may have a lot to say about her ex Ben Affleck, but that wasn't the only relationship Affleck had that was making headlines. In fact, it's hard to think of any Hollywood couple who got as much attention as Affleck and singer/actor Jennifer Lopez when they dated from 2002 to 2004.

The two met while filming the flop "Gigli" while Lopez was still married to her second husband, dancer Chris Judd. By November of 2002, the pair was engaged, with Lopez describing Affleck to Diane Sawyer (via People) as "brilliantly smart ... Loving. Charming. Affectionate," adding, "And I just admire him in every way."

While the two appeared to be deeply in love, the tabloids certainly put a strain on their relationship. Lopez even referenced the tabloid frenzy by putting Affleck in her music video for "Jenny from the Block." Lopez revealed, "We didn't try to have a public relationship. We just happened to be together at the birth of the tabloids, and it was like 'Oh my God.' It was just a lot of pressure."

That pressure sadly led to the couple's demise in 2004. But of course we know now, that wasn't really the end of Bennifer.

Ben Affleck marries Jennifer Garner and starts directing

Ben Affleck's career may have taken a hit from all the tabloid coverage of his love life and even struggles with addiction, but the actor appeared to make a comeback both personally and professionally in the mid-2000s. In 2005, Affleck married "Pearl Harbor" co-star Jennifer Garner.

The two welcomed daughter Violet later that year. The couple went on to have two more children, Seraphina in 2009 and Samuel in 2012, before sadly calling it quits after about a decade together. While the couple hasn't been romantically involved for some time, Affleck recently told the New York Times, "The biggest regret of my life is this divorce."

In 2007, Affleck also made somewhat of a career shift, with his directorial debut with the crime drama "Gone Baby Gone." While Affleck still acted in some films at the time, including the popular rom-com "He's Just Not that Into You," he kept his momentum as a successful director, this time with "The Town." While it was another crime drama, this time Affleck also starred in the film, which he did again with 2014's "Gone Girl."

Yet it was his 2012 film "Argo" that earned him the most accolades as a director. That film won the Oscar for Best Picture, as well as a Golden Globe for Best Director in 2013.

Ben Affleck is back in the headlines again

These days Ben Affleck is still putting out quality work, most recently with last year's highly praised "The Way Back." But like in years past, it's Affleck's relationship that is keeping him in the headlines. It appears we aren't the only ones revisiting the past (with this whole article), but also Affleck himself.

It's almost as if it's 2004 again because as of May 2021, Affleck has been seen spending time with ex-fiance Jennifer Lopez. Affleck took "The Wedding Planner" star to his Montana home following her split with fiance Alex Rodriguez. A source told People, "[Jennifer] spent several days with Ben out of town. They have a strong connection. It's all been quick and intense, but Jennifer is happy."

The two appeared to always keep a friendship over the years. Most recently Affleck commented on Lopez's InStyle cover, saying, "Why do you look the same as you did in 2003 and it kind of looks like I'm in my 40s ... at best?" Their hangouts these days may still be what it has been over the years, just friendly, but fans of course are hoping this time that it may be different. As for Affleck, he clearly hasn't done so bad himself in the aging department.