Skip to main content
Then & Now
November 21, 20256 min read

Ben Affleck's Three-Decade Rollercoaster: From Best Picture to Rock Bottom to Redemption

Ben Affleck has won Oscars, been mocked mercilessly, battled alcoholism, divorced twice, and somehow keeps coming back. His career is Hollywood's greatest survival story.

Share:

Ben Affleck has been Hollywood's golden boy, its biggest joke, its cautionary tale, and its comeback story—sometimes all in the same year.

He's won two Oscars. He's been in some of the worst-reviewed films of their decades. He's battled addiction publicly. He's been married twice to some of the most famous women in the world.

His career shouldn't exist. And yet here he is, still making movies, still relevant, still standing.

The Meteoric Rise (1997-1998)

Ben Affleck and Matt Damon's Good Will Hunting script won the Oscar. Ben was 25. He was on top of the world:

  • Best Original Screenplay
  • A-list status overnight
  • The next big thing
  • Friendship with Matt as Hollywood's favorite bromance

Everything seemed possible. And for a few years, it was.

The Crash (1999-2004)

Then came the fall:

  • Armageddon (entertaining but mocked)
  • Pearl Harbor (savaged)
  • Gigli (legendary disaster)
  • Daredevil (poorly received)
  • Jersey Girl (flopped)
  • Surviving Christmas (forgotten)
  • Paycheck (forgettable)

By 2004, Ben Affleck was a punchline. The Oscar winner couldn't pick a script. He was overexposed and underperforming.

The tabloids made it worse.

Bennifer 1.0

Ben's relationship with Jennifer Lopez became a media circus:

  • Constant paparazzi
  • The "Jenny from the Block" video
  • Engagement rings and over-the-top romance
  • Gigli flopping
  • The wedding called off

Bennifer became synonymous with celebrity excess and poor taste. The mockery was relentless. They broke up in 2004.

The Jennifer Garner Years (2005-2015)

Ben retreated. He married Jennifer Garner in 2005, had three children, and stepped out of the spotlight. He focused on:

  • Being a family man
  • Working less
  • Choosing better projects
  • Staying away from tabloids

It worked. The public started to forget the punchline and remember the actor.

The Director Redemption (2007-2012)

Ben Affleck's comeback came behind the camera:

  • Gone Baby Gone (2007): Acclaimed directorial debut
  • The Town (2010): Hit thriller he directed and starred in
  • Argo (2012): Best Picture Oscar

Argo was the triumph. Ben Affleck, the guy from Gigli, won the biggest award in film. The redemption was complete.

Or so it seemed.

Batman (2016)

Ben was cast as Batman in the DC Universe. Reaction was hostile—but he was actually good in the role. Critics praised his weary, older Dark Knight.

Unfortunately, the films (Batman v Superman, Justice League) were not good. And Ben's personal life was falling apart.

The Alcoholism Battle

Ben has been open about his addiction:

  • Rehab multiple times
  • Relapse after his divorce from Garner
  • Public incidents (visible intoxication at events)
  • Honest interviews about the disease

His struggle wasn't hidden. It played out in paparazzi photos and tabloid stories. But he kept working on recovery.

The Garner Divorce

Ben and Jennifer Garner divorced in 2018 after 13 years and three children. The cause:

  • His alcoholism
  • Alleged infidelity
  • His unhappiness
  • Growing apart

Garner has been gracious publicly. They co-parent effectively. But the divorce was clearly painful for both—and their kids.

The Return of Bennifer (2021)

In 2021, the unthinkable happened: Ben and Jennifer Lopez got back together.

They'd reconnected during her broken engagement to Alex Rodriguez. Within months, they were:

  • Publicly together
  • Engaged again
  • Married (for real this time, in 2022)

The internet loved it. A 20-year romantic arc with a happy ending. The Bennifer redemption.

The Second Divorce?

But by 2024, trouble emerged:

  • They stopped wearing wedding rings
  • They were rarely photographed together
  • They listed their home
  • Tabloids reported unhappiness

Jennifer filed for divorce in August 2024, two years after the wedding.

The fairy tale ending wasn't.

What Went Wrong (Again)?

The Bennifer 2.0 breakdown reportedly stemmed from:

  • Different lifestyles (she's glamorous, he's private)
  • His discomfort with fame
  • The meme of him looking miserable at events
  • Incompatibility that existed 20 years ago too

The same problems that ended them in 2004 ended them again in 2024. Some things don't change.

The Sad Ben Affleck Meme

Throughout Bennifer 2.0, Ben became a meme: cigarettes, exhausted expressions, visible discomfort at glamorous events.

"Sad Ben Affleck" was everywhere:

  • Smoking outside events
  • Looking miserable at premieres
  • Dunkin' runs while looking defeated

The memes were funny but also concerning. He didn't look happy. Maybe he wasn't.

The Career Continues

Despite personal turbulence, Ben's career keeps going:

  • Air (2023): Hit film he directed
  • Acting roles continue
  • Production company thriving
  • Respected as a filmmaker

He's learned to separate personal chaos from professional output. The work remains strong even when life isn't.

The Honest Interviews

Ben's willingness to discuss his struggles has earned respect:

  • He talks about addiction without excuses
  • He acknowledges his marriage failures
  • He's self-aware about his image
  • He doesn't pretend to have it figured out

That honesty is disarming. He seems like a guy doing his best—and often failing—in public.

The Survival

What's remarkable about Ben Affleck is simple survival:

  • 30 years in Hollywood
  • Multiple career deaths and resurrections
  • Addiction
  • Two high-profile divorces
  • Constant tabloid scrutiny

Most people would have cracked. He's still here, still working, still trying.

What's Next

At 52, Ben Affleck's future likely includes:

  • More directing (his strength)
  • Selective acting roles
  • Continued sobriety work
  • Co-parenting his kids
  • Probably more relationships

He'll never escape the tabloids. He'll never fully control his image. He'll probably have more highs and lows.

But he'll keep going. That's what he does.

The Lesson

Ben Affleck's career teaches that:

  • Second chances exist (and third, and fourth)
  • Talent can survive bad decisions
  • Honesty helps more than hiding
  • Hollywood loves a comeback
  • Some problems don't get solved, just managed

He's not a cautionary tale. He's a survival story—messy, incomplete, ongoing.

The Oscar winner who became a joke who won another Oscar who became a meme who might win another Oscar.

Only in Hollywood. Only Ben Affleck.