William Bradley Pitt is one of the biggest actors on the planet. The American heartthrob has done it all over his 35-year career. From a young Brad Pitt to the man he is today, the acting superstar has made his mark in cinema.

He’s starred in over 60 movies, won two Academy Awards (Best Picture for 12 Years a Slave and Best Supporting Actor for Once Upon a Time in Hollywood), a BAFTA for Best Film Actor in a Supporting Role in Once Upon a Time in Hollywoodtwo Golden Globes (Best Supporting Actor in 12 Monkeys and Once Upon a Time in Hollywood), a Primetime Emmy Award (Outstanding Television Movie with The Normal Heart), and two Screen Actors Guild Awards (Outstanding Ensemble Cast in a Motion Picture for Inglourious Basterds and Outstanding Actor in a Supporting Role in a Motion Picture for Once Upon a Time in Hollywood).

Some of his most impressive performances come in films such as The Curious Case of Benjamin Button, World War Z, Ad Astra, Moneyballand The Assassination of Jesse James by the Coward Robert Ford.

As well as all the accolades, Pitt’s production company Plan B Entertainment is responsible for a slew of critically acclaimed commercial hits, such as Moonlight, Kick-Ass, Minariand The Big Short. He’s also been a sex symbol for the better part of three decades and supports various humanitarian and political causes.

Then there are his famous romances. Pitt has been previously married to Jennifer Aniston and Angelina Jolie and involved in high-profile relationships with Juliette Lewis, Christina Applegate, Thandie Newton, Geena Davis, Sienna Miller, and Gwyneth Paltrow.

Recently Pitt has discussed how he believes his acting career is coming to an end, telling GQ he’s in the “last semester or trimester” of his career. In light of this news, we want to celebrate the great man’s journey and are doing so with these 15 photos from throughout his career.

15 Photos of a Young Brad Pitt Up Until Now

1. Just Starting Out

How young does Brad Pitt look here? This image is from an interview with the up-and-coming actor conducted in 1990. Although only 26 years old at the time, Pitt has a cockiness about him that is more charming than arrogant. You could already tell Pitt was going places.

2. Thelma & Louise

This is the film that first got Brad Pitt noticed. In the flick, he plays the drifter J.D. who captures the attention of Geena Davis’ Thelma. The two spend the night together and have a great time until J.D. flees the following morning with Thelma and her friend Lousie’s (Susan Sarandon) life savings.

Despite being a crook, Pitt’s charming personality and chiseled body had audiences, particularly women, all hot and bothered.

3. Floyd the Stoner

While his role in True Romance is extremely small, Brad Pitt steals every scene he is in. He plays Floyd, a jobless stoner who spends his days lying on the couch watching television. This role also resulted in a change of appearance for Pitt, who grew his hair long, giving him a surfer look the girls loved. Although the dodgy stubble on his chin isn’t the most attractive look, it works for Pitt.

4. Legends of the Fall

Pitt continued growing his hair long for his roles in Legends of the Fall and Interview with a Vampire. These are the two movies that really put Pitt on the map. Of those two films, it’s the Americana look he sports in Legends of the Fall that helped him stand out.

Long blonde locks flowing and clean-shaven, Pitt is an absolute dreamboat. His acting is top-notch also, with the movie earning $160 million at the box office opposite a budget of just $30 million.

5. The Gwyneth Paltrow Era

Meeting on the set of SevenBrad Pitt and Gwyneth Paltrow seemed the perfect match. The two dated from 1994 to 1997 and even got engaged, but sadly things didn’t last. Paltrow called it quits, believing she wasn’t ready to settle. Considering she was 22 at the time that makes complete sense.

Even though their relationship didn’t last, they provided the paps with plenty of photo opportunities. They were one of the it couples of the 90s, with the above image showing the loved-up duo on a night out.

6. 12 Monkeys

One of Pitt’s most underrated performances is that of a psychotic mental patient in the sci-fi flick 12 Monkeys. Pitt cut his hair short for the role and acts all twitchy and weird, really going for it. The film was a box office smash and further cemented Pitt as one of the must-watch actors in the world. He won a Golden Globe Award for Best Supporting Actor and the film made over $168 million worldwide.

7. Meet Joe Black

Brad Pitt went blonde for his role as Joe Black, who just happens to be Death in human form. The movie didn’t do well critically but was another big hit with moviegoers. This film, along with his cameo in Sleepers and larger roles in The Devil’s Own and Seven Years in Tibet solidified Pitt’s leading man status.

8. Brad and Jen

After his engagement to Gwyneth Paltrow ended, it wasn’t long until Brad Pitt found himself in the arms of another famous lady. He was set up on a date with Jennifer Aniston by his manager in 1998. The pair hit it off spectacularly, with Pitt proposing a year later on stage at a Sting concert.

This photo of the duo was taken at the Erin Brockovich premier in 2000. Although 36 at the time, Pitt still looks super young, helped no doubt by his stylish haircut and having Aniston on his arm.

Sadly Pitt and Aniston called it quits after seven years together. The rumored cause of the split was Pitt cheating on Aniston with Angelina Jolie, but everyone has denied that. It was just time for both parties to move on in life.

9. The First Rule of Fight Club Is You Do Not Talk About Fight Club

One of Brad Pitt’s most iconic roles is that of Tyler Durden in David Fincher’s Fight Club. Alongside Ed Norton, who was arguably as big as Pitt at the time, the two delivered incredible performances in this hard-to-define masterpiece. Although it received mixed reviews, Fight Club found a cult on VHS and is now considered one of the great films of the 90s.

It’s also memorable for Pitt’s impressive physique, with the actor absolutely ripped. Some even think this is the ultimate Brad Pitt movie. This is a look he would take into his next couple of movies, with his heartthrob status at its peak.

10. Happier Times

Before their marriage ended in a bitter divorce, Brad Pitt and Angelina Jolie were Hollywood’s golden couple. The two fell in love on the set of Mr & Mrs Smith are were quickly dubbed “Brangelina” by the paparazzi. They were together for 11 years and had six children (three of those adopted) before things fell apart.

While together they always appeared to be deeply in love with each other, and this image is a great snapshot of the two together at the Cannes Film Festival in 2010.

11. Call Me Mickey

For his role in Guy Ritchie’s SnatchBrad Pitt made himself look less than flattering. While still sporting a six-pack, Pitt’s messy hair and three-day growth gave him the appearance of someone who hasn’t showered in weeks.

Playing an English gypsy, Pitt’s speech is near unintelligible, only adding to the character. Playing against type, the movie showcases Pitt’s acting ability and versatility and is one of his best performances.

12. The Ocean’s Trilogy

These films all vary in quality, but Brad Pitt is front and center in all three of them. Sharing a screen with the likes of George Clooney, Matt Damon, and Andy Garcia, Pitt is never overshadowed and holds his own. He’s a big part of the franchise and showcases his handsome good looks throughout.

13. Inglourious Basterds

As Lieutenant Aldo Raine, Brad Pitt offered something completely different in the Quentin Tarantino hit Inglourious Basterds. Playing a southern soldier in charge of a company of men who hunt down Nazis, Pitt sports a bouffant hairstyle with a small mustache. Even at 45, he still looks in great shape and has a commanding on-screen presence.

14. The Stuntman

Brad Pitt is the epitome of cool in Quinten Tarantino’s Once Upon a Time in Hollywood. His character Cliff Booth, the stuntman and best friend of Leonardo DiCaprio’s Rick Dalton, is a classic Hollywood archetype with his ripped abs, cinematic good looks, and charming personality. The role won Pitt his first Academy Award for acting and is a credit to his entire career.

15. Refined Brad

Now that he’s getting on in years, Brad Pitt is often seen dressing smartly. Of course, there are still images of him with a dirty beard or stringy long hair that pop up from time to time, but generally speaking, when he’s not filming, Pitt looks pretty good. This shot of him in a tuxedo with a little facial hair and semi-long hair proves he’s still a good-looking rooster.