By Jessica Wedemeyer
3:00pm PST, Dec 18, 2023
_
Brad Pitt has long been one of Hollywood's most handsome leading men. To celebrate his milestone 60th birthday on Dec. 18, 2023, we're taking a look at our favorite photos of the Academy Award-winning actor back in the day…
Brad Pitt looked like a classic movie star while portraying real-life mountaineer Heinrich Harrer in 1997's "Seven Years in Tibet."
Keep reading for more pics of Brad early in his career…
MORE: Josh Hartnett's hottest moments from the '90s and 2000s
_
That jawline is what dreams are made of! Brad Pitt is seen here during the MTV Video Music Awards in 1990. The best part about this pic? It's candid! Brad naturally looks this good.
_
What we didn't know we needed? This throwback pic of Brad looking gorgeous in a pastel green-and-blue sweater vest. The Hollywood hunk is seen here at the premiere of "The Pallbearer" in 1996.
_
Brad Pitt was absolutely irresistible when he starred as Tristan Ludlow in 1995's "Legends of the Fall."
_
That hair! Those glasses! Brad Pitt, seen here at the "Red Heat" premiere in 1988, brought the heat himself! A leather jacket has never been worn so well.
_
Could he be any more '90s?! Brad Pitt is seen here in 1992 in a backwards cap, a black button-down and light-wash jeans.
_
What a throwback! Brad is seen here at the Jimmy Stewart Relay Marathon Cocktail Reception in Los Angeles in 1988. From his dirty blonde locks to his oversized leather jacket, he was the ultimate baby-faced hunk!
_
A beanie on the red carpet? Unconventional, but Brad Pitt pulled it off! The Hollywood hunk is seen here at the Writers Guild of America Awards in 1998.
_
In need of some serious late-'80s fashion inspiration? Look no further. Brad Pitt attended the premiere of "Eddie & The Cruisers 2" in 1989 looking incredibly stylish for the time.
_
Two Hollywood icons in one photo! Brad Pitt and Tom Cruise posed for photographers at the Los Angeles premiere of their movie "Interview with the Vampire" in 1994.
_
Brad Pitt flashed a winning grin as Frankie McGuire in 1997's "The Devil's Own."
_
Brad Pitt raised temperatures as J.D. — his first big movie role — in 1991's "Thelma & Louise."
_
He sure was a fan of hats, huh?! Brad Pitt, seen here at an album listening party in 1989, melted hearts with his signature smize and baby-faced good looks.
_
Look at that smolder! Brad Pitt's luscious blonde locks and piercing blue eyes took center stage in this photo from 1991.
_
We're not quite sure what we adore more — Brad Pitt's dramatic sunglasses or his baby pink bandana! The heartthrob is seen here posing up a storm in a 1988 photo session.
_
Buzz cut Brad! In 1999, Brad Pitt looked like a total stud when he attended a Hole concert in a simple gray tee and a dark brown leather coat.
_
Brad Pitt was still sporting the super-blonde hair he had in the film when he attended the premiere of "Seven Years in Tibet" in October 1997.
_
Brad Pitt gave a smoldering look when he posed for promotional photos for "Dallas." He portrayed Randy, Charlie Wade's boyfriend, on four episodes between 1987 and 1988.
_
Cutie! While filming "Meet Joe Black" in 1997, Brad Pitt was photographed in a laid-back outfit: a long-sleeved shirt, light-wash denim and sneakers.
_
Brad Pitt's Achilles may have been a mere mortal, but the actor looked every inch a golden god in 2004's "Troy."
_
Brad Pitt channeled George Michael while portraying a rock star (alongside Jeremy Miller's young Ben Seaver) on a 1989 episode of "Growing Pains."
_
Brad Pitt and Angelina Jolie's chemistry was palpable when they co-starred in 2005's "Mr. & Mrs. Smith." (The former couple have admitted they fell in love on the set of the steamy action flick!)
_
So suave! In this photograph taken in 1995, Brad Pitt looks like the ultimate cool guy in his oval shades and black velvet blazer he dressed down with blue jeans and a cream-colored sweater over a white tee.
_
2008 marked the year in which Brad Pitt played Chad Feldheimer in 2008's "Burn After Reading." What a dreamboat!
_
What's he laughing about?! During the "Legends of the Fall" premiere in 1995, Brad Pitt had hearts racing with his gorgeous smile and piercing blue eyes.
_
Brad Pitt made us swoon when he starred as Louis in 1994's "Interview with the Vampire."
_
How dashing! In 2016's "Allied," Brad Pitt played a suave secret operative from Canada, Max Vatan, alongside Marion Cotillard's stunning undercover French Resistance fighter.
_
We loved him in this role! In 2011, Brad Pitt starred in the sports biopic "Moneyball." He portrayed Oakland Athletics General Manager Billy Beane.
_
Brad Pitt played a suave veteran-turned-detective in 1992's "Cool World."
_
That smile is everything! Brad Pitt is seen here during the Academy Awards in 2000. He sure cleans up well!
_
We wonder what he was laughing about! In 1997, Brad Pitt was all smiles during a photocall in Rome for his film "Seven Years in Tibet."
_
Congratulations, Brad! At the 2001 Golden Globes, Brad Pitt took home the award for best supporting actor for his performance in "12 Monkeys." He sure cleaned up well too!
_
The pout! The hair! Those eyes! There was just so much to love about Brad Pitt in 1989's "Cutting Class."
_
It doesn't get more early aughts than this! In 2001, Brad Pitt attended the "Rock Star" film premiere in tinted glasses with flashy silver hardware.
_
In 1997, Brad Pitt and then-girlfriend Gwyneth Paltrow attended the premiere of "The Devil's Own" in New York City sporting matching blonde haircuts. Brad, who smoldered on the red carpet, co-starred in the film alongside Harrison Ford.
_
Cute! The year was 1996 when Brad Pitt portrayed handsome New York City native Michael Sullivan opposite Jason Patric in "Sleepers."
_
A '90s hunk! Brad Pitt is seen here arriving at the Los Angeles premiere of "Thelma & Louise" in 1991.
_
Brad Pitt mastered the perfect pout as Walker Lovejoy on FOX's short-lived series "Glory Days" in 1990.
_
Death never looked hotter than when Brad Pitt starred as Joe Black in 1998's "Meet Joe Black."
_
We're not sure what we love more: Brad Pitt's signature smolder or the gorgeous leather coat he's rocking! He's seen here at the Los Angeles premiere of his film "Ocean's Twelve" in 2004.
_
How edgy! Brad Pitt is seen here at the "Mr. & Mrs. Smith" Los Angeles premiere in 2005 rocking a seriously bleached-blonde 'do.
_
Looking good! In 1998, Brad Pitt attended the Los Angeles premiere of "Meet Joe Black," in which he starred alongside Anthony Hopkins and Claire Forlani.
_
Brad Pitt's baby blues sparkled when he starred as Detective David Mills in the 1995 crime-thriller "Seven."
_
Brad Pitt flaunted his fit physique as boxer Mickey O'Neil in 2000's "Snatch."
_
Brad Pitt was a dreamboat in 1991's "Johnny Suede." Just look at that massive pompadour!
_
We love that printed shirt! Brad Pitt and Christian Slater attended the premiere of their film "True Romance" in 1993.
_
Brad Pitt and then-girlfriend Angelina Jolie held on tight at the premiere of his movie "The Assassination of Jesse James by the Coward Robert Ford" during its Toronto International Film Festival premiere in 2007.
_
Who knew fly fishing could be so sexy? Brad Pitt looked adorable as Paul Maclean in 1992's "A River Runs Through It."
_
Even with a patch of hair on his chin and that unfortunate haircut, Brad Pitt still looked good at the 1999 Venice Film Festival.
_
Brad Pitt was so bad he was good when he played Tyler Durden in 1999's "Fight Club."
_
Brad Pitt is seen here as zombie-fighting hero Gerry Lane in 2013's "World War Z."
_
While we weren't huge fans of his hair here (sorry, Brad!), this one's still a worthy throwback. Brad Pitt is seen here at the premiere of "Solaris" in 2002.
_
It might have something to do with his job description, but we sure love Brad Pitt as First Lieutenant Aldo Raine in the World War II-set 2009 film "Inglourious Basterds."
_
Brad Pitt looked sexy while brooding in black as the titular outlaw in 2007's "The Assassination of Jesse James by the Coward Robert Ford."
