Getting Into the Business

From an early age, Affleck shows an interest in acting. After appearing in a Burger King ad, he lands the part of C.T. Granville on the PBS miniseries The Voyage of the Mimi. The 13-episode educational program follows the crew of the Mimi exploring the ocean. "I was [a kid] when I did this science show," he tells Entertainment Weekly in 2007. "Sometimes I think I grew up too fast."

Spring

Partying 101

Affleck and pal Matt Damon graduate from Cambridge Rindge and Latin High School in 1990. There, he tells Details, the two spent their time "underage drinking, pot smoking and all the attendant shenanigans." After a few transfers, he drops out to pursue acting with roles in Buffy the Vampire Slayer and School Ties before landing his first substantial part in the cult classic Dazed and Confused.

Let's Just Do It

After Damon's creative writing teacher at Harvard encourages him to hold on to the play version of Good Will Hunting he wrote for class, Damon brings it to L.A., not knowing what to do with it. He shows it to Affleck: "[Affleck] took a look at it and he said, 'Well, we should really write this together,'" Damon recalls in an interview with Rough Cut Online. "So we just started writing this thing one night. And it just tumbled out."

December 05

Hunting for a Deal

Affleck and Damon debut the film they co-authored, Good Will Hunting, about a troubled math prodigy who is a janitor at MIT. Miramax co-chairman Harvey Weinstein buys the project for almost $1 million. "We never expected anyone to see it, which was why [it] was successful," Affleck tells EW. It is nominated for nine Oscars and wins two, including Best Original Screenplay, which Damon and Affleck happily collect. "This is a little overwhelming for two guys who never won a raffle," Affleck tells PEOPLE.

July 01

New Action Hero

Affleck gets the first of many action roles, starring opposite Bruce Willis and Liv Tyler in the blockbuster Armageddon. "A lot of it really hasn't sunk in," says Affleck, who also had to get used to his new popularity with female fans. "The pinup aspect is part of the game," the actor tells PEOPLE. "I think you're naïve if you want to be an actor and you don't expect that people will see you that way. Hey, young guys, pinup guys, that's what sells."

October 09

Red Light, Green Light

Affleck and Damon premiere their HBO reality show Project Greenlight, meant to help talented screenwriters get the green light. "We have been the beneficiaries of very good fortune," Damon tells PEOPLE. "So one of the reasons we're doing this is because it's karmically appropriate for us to use our position to give someone else an opportunity." As an actor, in June 2001, Affleck takes on his biggest role to date as a dashing Navy pilot in the World War II blockbuster Pearl Harbor.