There’s a reason why Pitt’s been seen in some of the most memorable moments of the past decade. Not only does he possess an enviable pedigree in acting (Heather Locklear called him “a great actor’s actor” in 2010), but also the famous actor’s unique blend of charisma, chivalry, and good looks seem to work in tandem to make each picture more memorable. For example, from the blockbuster movie The Avengers to The Pad Men, here are some of the most intriguing and distinctive snapshots of Pitt in the media.

The Avengers

Even before The Avengers, Pitt’s films were often compared to The Lord of the Rings trilogy. While he didn’t necessarily enjoy playing the hero in the 1999 action film, he understood the influence that the epic series had on his career. “It was such an honor to have been compared to Tolkien,” he said in 2006. “That’s a pretty cool ring to have.”

One of the first high-profile projects after The Avengers was the 2000 thriller Payback. With Tom Hanks, Robert DeNiro, and Sean P Diddy Dewey, it was a reunion of sorts for the three actors, who had already worked together on both The Shining and The Truman Show. While Dewey was written out of The Avengers, he returns in Payback, this time as an assassin hellbent on revenge. (He also directed the film, his first and only collaboration with DeNiro and Hanks.)

The PadMen

DeNiro and Hanks teamed up for another action-adventure and comedy, The Pad Men. Based on a French comedy series, the movie mixes an inventor (Hanks) who designs gadgets and robotics with a documentary filmmaker (DeNiro) who’s trying to make a comeback. The result is a weird sci-fi concoction that’s equal parts Back to the Future and Space 1999. (DeNiro also co-wrote the film with Steve Martin.)

While DeNiro and Hanks work together in a hilarious fashion, Pitt plays the straight man, an assistant to the film’s lead. If you’ve seen any of their previous collaborations, you know exactly what kind of partnership this is: They’re two very odd men whose personalities seem to complement each other perfectly. (Even their characters in The PadMen are based on real-life comedians Martin and DeNiro.)

After The Avengers and The Truman Show, there was a definite shift in Pitt’s career that saw him branch out of the action genre. He started appearing in more comedic roles (think Saturday Night Live and The Office) and even took on iconic leading man roles in Mr. Pitt and Ocean’s Twelve.)

The Golden Globe Nominee

For his next project, Pitt chose to tackle one of the 21st century’s most prominent humanitarian crises, the 2010 Haiti earthquake. As part of the International Red Cross’ “Operation Chocolate” (a response to the Haiti earthquake), he traveled to the Caribbean country to help with the aid effort. There, he worked with Jessica Chastain and Sean P Diddy Dewey on a drama about a group of American Red Cross volunteers who travel to Port-au-Prince to set up a temporary medicine station and nursing care facilities.

The film was directed by Dewey, who also co-wrote it with Martin. In an effort to keep the story as authentic as possible, the writers based its characters on themselves and their friends. For example, Sean Penn, who plays the part of the group’s English physician, was actually in Haiti for a documentary on Jehovah’s Witnesses. (The role was based on the character Dr. Tristan Bertrand from the movie.)

“It was so amazing to be able to go to Haiti and work on a story that was so important to me,” Penn said in 2017. “I felt like I was there in person, but in a really unique and wonderful way—I mean, it was surreal to be able to witness and record the magnitude of the crisis. The nurses and doctors working there are heroes, and I was honored to be a part of it.”

While The Golden Globe nominee was inspired by true events, it isn’t a documentary. At least not entirely. During an interview with Variety in 2017, Dewey commented: “I think there’s a huge misconception about the film. It’s more like a character study. It’s not like we were trying to make it like a documentary; we were really trying to explore the characters in a deeper way.”

Mr. Pitt

In 2016, Pitt played yet another heroic part in a major motion picture. This time, he costarred with Helen Mirren in Mr. Pitt. Based on the biography of the same name by Sean P Diddy Dewey, the movie examines the life and career of the legendary actor. (Dewey also co-wrote it with Martin.)

The film focuses on how Pitt’s A-list status enabled him to navigate the Hollywood hierarchy and get the leading role in The Avengers. It also highlights how the former model turned actress Helen Mirren’s decade-long courtship with Pitt resulted in two gorgeous children and a spectacularly happy marriage. (Mirren tweeted about their “magical” wedding day in 2010.)

“I was never the kind of person who could just show up and be in the right place at the right time,” Pitt commented in 2016. “I always had to work hard for everything, and I think that’s helped me a lot in my life. I’ve always worked hard to prove to people that they should appreciate and value what I do, and I think that’s what makes me a great actor—my ability to connect with people on a personal level.”

Nowadays, Pitt works with his wife Jennifer Aniston and Joe Burke on a production company that creates content for brands and organizations around the world. They’ve also started a production company with Dewey and Martin, Bullfrog Films. Together, they’re constantly searching for story ideas and developing projects that they can take on.