July 27

Risky Business

After a blowout gambling trip to Las Vegas, Affleck returns to L.A. with $800,000 and the realization that he has a drinking problem, PEOPLE reports. Affleck calls pal Charlie Sheen, who drives the actor to Promises, the $33,850-a-month rehab center. His father, a recovered alcoholic who has been sober since 1990, tells PEOPLE his son "is doing the best he can to thread his way through the miasmic nightmare of celebrity," and Affleck later tells Details, "You're just a bad night away from a big E! True Hollywood Story."


Ben Affleck


Display of Affection

While working on Gigli with Jennifer Lopez, Affleck raises eyebrows by placing an ad in the Hollywood Reporter extolling his costar's "graciousness of spirit, beauty and courage, great empathy, astonishing talent, real poise and true grace." She is still married to her backup dancer Cris Judd. Then, Affleck shows up to help Lopez celebrate the opening of her Pasadena restaurant Madres, giving her a floral arrangement while Judd stood by.

Ben Affleck


OK, Fine, We're Dating

After hanging out together for months (and after Lopez's divorce). Affleck and Lopez come out as "Bennifer" in her "Jenny from the Block" video. In the video, they kiss, and read tabloid reports about themselves. Affleck also strokes Lopez's famous posterior. He gives his new love a token of his affection, a yellow-and-white-diamond bracelet.

Ben Affleck


All Shiny & New

Affleck presents Lopez with a 6.1-carat pink-diamond solitaire ring custom-made by Harry Winston. With Lopez's help, a new and improved – polished, tanned and buffed – Affleck becomes PEOPLE's Sexiest Man Alive.


Ben Affleck


Super Man

Affleck becomes a superhero, starring opposite Jennifer Garner in Daredevil. "He's your basic tall, dark and handsome. He's it. You want him to save you," Garner says to PEOPLE. "I can't imagine anyone in the world I would rather see swoop in and save the day than Ben."

Ben Affleck

July 17

Trouble Brews with a Rag & a Dud

The National Enquirer runs a story about Affleck's wild night at a Vancouver strip club. It causes trouble for the pair, but Lopez gets over it, telling Affleck, "You've had your bachelor party." A month later, Gigli is released, and is critically panned. The L.A. Times says it is "nearly as unwatchable as it is unpronounceable."

September 29

The Wedding That Never Was

Four days before their $2 million wedding, Affleck and Lopez call off the event. "As the [wedding] date got closer, reality set in that this may not be the person Ben wants to spend the rest of his life with," a friend tells PEOPLE.

Ben Affleck

Early December

Getting Away

With his relationship on the rocks, Affleck visits the troops in Iraq. That January, Lopez breaks up with him. "She finally realized they were never going to get married," a close source tells PEOPLE. By June, Lopez marries Marc Anthony.


Ben Affleck


A New Beginning

Affleck begins dating his Daredevil costar Garner when he goes to shoot a short scene for her Daredevil spinoff Elektra. Though the scene was cut from the film, the relationship endured. Affleck tells Details, "I want to get married and start a family."


Citizen Affleck

Affleck helps campaign for Democratic candidate (and Massachusetts native) John Kerry. Kerry doesn't win, and George W. Bush is later quoted in PEOPLE as saying, "I think endorsements are great to generate publicity, but no one really listens to anybody else's endorsements."

Photo Credits


Edited by Julia Wang

Ben Affleck

Celebrity Central / Top 25 Celebs