20 Flashback Photos of Brad Pitt That Prove He’s Always Been a Dreamboat

By Jess Catcher Updated: September 6, 2019

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Brad Pitt can be seen today showing off his acting talents (and chiseled physique) in Once Upon a Time… In Hollywood, but the 55-year-old actor has been steaming up our screens for decades now. Although we’re certainly impressed with how he’s maintained his iconic good looks over the years, we can’t help but want to take a look back at some of his younger days in the entertainment industry.

Did you know one of Pitt’s earliest roles was on a daytime soap opera? Or which film won him a Golden Globe for Best Supporting Actor?

We reached way, way back to find some of the best throwback photos of Pitt throughout his impressive career. He’s more than just a pretty face, of course, but there’s no harm in admiring his charms.

Take a look at all the throwback photos that prove Brad Pitt has always been a dreamboat.

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Long before most of us knew the name Brad Pitt, the actor showed off his charming smile in this snapshot from 1988.
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One of Pitt's earliest roles was alongside Shalane McCall, posing with him and Goofy in 1998, on the soap opera Another World.
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How cute is he with these horn-rimmed glasses in 1988? This is giving us some serious be-speckled James Dean vibes.
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Did this pic from 1988 predict Pitt's role in Interview with the Vampire later on in 1994?
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Pitt posed here on the set of Growing Pains in 1989, his second guest appearance on the show. Later, his Once Upon a Time In Hollywood co-star Leonardo DiCaprio was added to the same series in 1991.
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This shot of the actor in 1989 looks like he was practicing his "nonchalance" pose.
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Pitt looks like he brought his A-game to the drama of this 1989 pilot for a show called The Kids Are Alright.
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It might be hard to believe this isn't a current photo of Pitt, but this is the actor posing oh-so-coyly outside a movie theater in 1989.
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Pitt paired yet another casual-yet-chic outfit for the Thelma & Louise (1991) Los Angles premiere with some very stylish glasses.
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Pitt's role in Thema & Louise was small, but ultimately led to his breakthrough in Hollywood — and he obviously got along well with stars Geena Davis and Susan Sarandon!
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It's easy to see why he's often compared to his A River Runs Through It director, Robert Redford, judging by this photo from the 1992 film.
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This beardy photo of Pitt in 1992 at the premiere of his movie Johnny Suede looks like it could have been taken yesterday.
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Pitt seemed to like growing out a shaggy beard and haircut in 1992, but we're honestly too distracted by his eyes in this photo.
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In 1993, Pitt was clearly inspired to let his hair grow out even longer after co-starring in True Romance.
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But then Pitt got rid of his locks all over again while promoting his film Legends of the Fall, posed here with this sly smile in 1995.
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After years of hard work, the actor won a Golden Globe for his performance in Twelve Monkeys at the 1997 ceremony.
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If this crooked smile in a candid while filming Meet Joe Black in 1997 isn't making you swoon, well, we don't know what will.
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Pitt brought in plenty of '70s swagger for the premiere of Seven Years in Tibet.
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Here he is just hanging out with a couple of pals in 1998 — who just happen to be Keith Richards and Ronnie Wood, members of the Rolling Stones.
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We aren't sure what Pitt might have been saying in this photo from a press conference in 1998, but we can guess it was pretty darn charming. Naturally!

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