And oddly, it was the role of a Midwestern drifter in "Thelma and Louise" that launched Pitt into super-stardom.
He became an instant heartthrob, known as much for his smile as his blonde locks.
"Do you feel like you have to fight your looks though, at times?" Cowan asked.
"Listen, I mean, we all deal with the cards we've been dealt. And I've been dealt some pretty - a pretty good hand. Pretty good cards!"
His high-profile romances were like catnip for the tabloids - his engagement to Gwyneth Paltrow, and then his marriage (and very public divorce) from Jennifer Anniston - took on a life of their own.
But even they paled in comparison to Angelina Jolie, so famous the couple has a single nickname: Branjolina.
They've been together now for seven years, and have six children - three of them biological, the other three overseas adoptions.
"I couldn't imagine life without any one of them," Pitt said. "There's just something that happens."
They go everywhere their parent's work takes them.
"Listen, I admit there's times like, 'We gotta get up. Get up! Here's your shoes. Here's your shoes. Drink this Coke. Drink this Coca Cola. Drink it all. Right now! Drink it! Drink it! Drink it! Just so we could get 'em up and going," Pitt said.
And travel-weary or not, they seem very aware their parents aren't married - yet.
"We're getting a lot of pressure from the kids," Pitt noted. "Yeah, it means something to them and they're, you know, they have questions when their friends' parents are married and why is that?"
"So what do you tell them?" Cowan asked.
"We will someday, we will: 'That's a great idea! Get mommy a ring! Okay, I will, I will.'"
"Do they have a sense of you and Angelina are as famous as you are? I mean, do they get that?"
"They know that mommy and daddy work in films and stories," said Pitt.
But of the paparazzi? "Well, you know, they think everyone has to deal with that. Four of mine aren't bothered by it, two of them are. They just don't like it. Don't like it."
"How do you deal with that, though?" asked Cowan. "I mean, really deal with it because you deal with it on a scale that other people can't even imagine."
"When it first hit, it was very discombobulating and I would, would repel from it. And now I see it as, as something that can be used for good things."
One of those good things is his non-profit work in New Orleans, where he's helping rebuild the Lower 9th Ward in the wake of Hurricane Katrina.
"What made me so angry was this idea that 'It was an act of God,'" he said. "That if you lived on the coast, 'That's what happens.' And it wasn't. It was a failure of man. And a lot of people died. And for me there's a responsibility to make it right."
His Make It Right Foundation has replaced some homes that were lost, with solar-powered alternatives that create more energy that the occupants use, redefining low income housing.
His good friend George Clooney used the Golden Globes to highlight Pitt's good deeds - and there are plenty more of those red carpet award shows to go, which has Pitt busier than ever.
"It is fun for you?" Cowan asked.
"It IS fun, it's, it's ..."
The word Pitt's looking for is: long.
"I would prefer if we could do it on one weekend, instead of three months or two months, whatever it is," Pitt replied. "I think it should be, like the 24-hour Le Mans. Like we just run 'em all back-to-back, go into the broadcasts, Golden Globes, SAG, and 24 hours later at the end, have the Oscars, and last man standing takes it all!"