While he is sometimes considered more famous for his good looks and glamorous lifestyle, it should not be forgotten that Brad Pitt is an excellent actor, having appeared in some of the best films of the last 25 years. The 51-year-old is one of the most recognizable and powerful people in the entertainment industry, but he often doesn’t receive the critical respect he deserves due to the constant media exposure of his personal life. In addition to playing “eye candy” roles, Brad Pitt has frequently taken on gritty, flawed, and complex characters in many intriguing movies, with the following 10 performances proving he’s one of the best actors of his generation.

10. Thelma & Louise (1991)

For Brad Pitt, it all started with a minor role in the 1991 classic, Thelma & Louise. While Ridley Scott’s film remains iconic in terms of its feminist overtones, it was also the movie that launched Pitt’s career and turned him into a Hollywood sex symbol. This of course also created problems for Pitt, as at times he has struggled to shake this label, and there are several films (not included on this list) that play into this typecasting. In Thelma & Louise, Pitt plays the role of J.D, frequently shirtless drifter who hitches a ride with the titular duo. It turns out he is a thief who has broken parole, and he ends up stealing their money. Although not the most complicated character, Pitt excels in the role as an attractive, cool, and charming man, and this would pave the way for him to become the next big Hollywood star.

9. A River Runs Through It (1992)

Brad Pitt would land his first major role in a big-budget production in Robert Redford’s 1992 drama, A River Runs Through It. It’s a period drama based on the semi-autobiographical novella of the same name and saw Pitt play Paul, brother of Norman (Craig Sheffer). Told from the point of view of Norman, the film explores the boys being raised by their strict minister father (Tom Skerritt), and them returning home after becoming troubled adults. It was a great vehicle for Pitt to showcase his acting talent and to prove that he was a skilled actor who could perform in slower paced films. He and Skerritt work well off of each other, and working with such a talented team certainly helped Pitt in these early stages of his career. While not the most dramatic of films, the stunning cinematography (which earned an Academy Award) and brilliant score helped its popularity, as well as Pitt’s.

8. Legends of the Fall (1994)

For many, Legends of the Fall is what cemented Brad Pitt as a Hollywood star. The 1994 epic-drama, based on the 1979 novella, is directed by Edward Zwick and also stars Anthony Hopkins, Aidan Quinn, Julia Ormand, and Henry Thomas. The film spans the period before World War I, through the Prohibition era into the 30s and ends in 1963. The story sees three brothers and their father living in the remote wilderness, and follows how issues at the time impact their lives. Pitt plays the role of Tristan Ludlow, who is the middle brother, and the most wild and complex of the three. It’s touching, dramatic, and heartfelt throughout, and Pitt steals the show in each of his scenes thanks to a challenging role as a character who goes through a lot of trauma. He picked up a nomination for a Golden Globe for his performance.

7. 12 Monkeys (1995)

12 Monkeys was one of our first glimpses of Pitt as a dark, complex character, and this helped showcase his diversity as a performer, which we saw more throughout the late 90s. This 1995 science fiction film, directed by Terry Gilliam, stars Bruce Willis and sees Pitt play the role of Jeffrey Goines. Cole (Willis) is a prisoner from the future  haunted by dreams of his own death, and is sent back in time to collect an un-mutated sample of the plague that has destroyed humanity. In 1990, he is placed in an insane asylum where he meets Jeffrey Goines, a patient and activist with fantastical views. The weaving story is helped by Pitt’s manic and frenzied character, often overshadowing Willis in what is now a sci-fi classic. Pitt’s performance in 12 Monkeys saw him pick up his first Academy Award nomination for Best Supporting Actor.

6. The Curious Case of Benjamin Button (2008)

The Curious Case of Benjamin Button is a peculiar story of a man who ages in reverse. It has drawn comparisons to Forrest Gump in that it’s an account of a man’s life from start to finish (or in this case, the reverse), and although the premise is not for everyone, Pitt’s fantastic performance carries the film.. Pitt plays the titular character as an adult, and gets to showcase his versatility all in one role by playing a young-minded 70-year-old, through to a young kid suffering from Alzheimer’s. Some of the credit must also go to the CGI and makeup used in the film, as they makes his transformation a shocking and visually impressive one. Pitt’s wonderful performance in a hugely challenging role saw him earn his second Academy Award nomination and first for Best Actor.

5. Inglourious Basterds (2009)

Any actor would jump at the chance to work with Quentin Tarantino, and Pitt got his opportunity with the 2009 film Inglourious Basterds, where he starred alongside Christopher Waltz, Diane Kruger, Michael Fassbender, and Eli Roth. The film has five acts and covers conflicts in WWII-era Europe, including two separate plots to assassinate Nazi Germany’s political leadership. In typical Tarantino fashion, it’s fun, stylish, and quirky, putting a new spin on the typical war movie formula. While Waltz earned most of the plaudits for his role as SS Colonel Hans Landa, Pitt also puts in an excellent performance as Lieutenant Aldo “The Apache” Raine. Aldo Raine leads the “Basterds”, who hunt Nazis behind enemy lines. He’s almost cartoonish, with a strong accent and brilliant facial expressions, and his character is integral in making Inglorious Basterds yet another fun, bloody, and wild Tarantino classic.

4. Snatch (2000)

Brad Pitt isn’t often known for playing more comical roles (especially earlier in his career), but he proved that he could excel at dark humor through his performance in Guy Ritchie’s 2000 British gangster film, Snatch. Pitt perfectly plays the role of Mickey O’Neil, an Irish gypsy who also happens to be a phenomenal boxer. Much of the humor comes from his extremely thick Irish accent, which causes much confusion for the other characters (and the audience). When Tommy (Stephen Graham) and Gorgeous George (Adam Fogerty) go to buy a caravan from some Irish travelers, they discover Mickey and his talent for boxing and recruit him to fight for them in an attempt to win money. Suffice it to say, they quickly realize that he is not a person you want to tangle with. Much like another Guy Ritchie vehicle, Lock, Stock & Two Smoking Barrels, Snatch is intelligent and well-crafted, thanks in large part to Pitt and his unconventional, comedic performance.

 3. Moneyball (2011)

In addition to acting, Brad Pitt has also proven himself a successful producer in recent years, with credits including The Departed, 12 Years a Slave, The Tree of Life, and Moneyball. He also stars in the last-mentioned film, which is a biographical sports drama based on the 2003 book of the same name. It follows the Oakland Athletics’ baseball team in the 2002 season and their attempt to assemble a talented squad with a limited budget. To do this, they adopt an advanced sabremetrics approach to scouting to build an undervalued, but skilled squad. This may sound like a film only for baseball fans, but Pitt’s masterful performance as GM Billy Beane, Jonah Hill in the supporting role, and the direction of Bennet Miller make Moneyball a thrilling, intriguing and unique sports film. It would prove to be a box-office smash, and would earn six Academy Award nominations (including Best Actor for Pitt).

2. Seven (1995)

Most would agree that Seven is much more than your average crime thriller, and this is largely due to the fantastic performances from Brad Pitt and Morgan Freeman, as well as a chilling Kevin Spacey. Seven is also masterfully directed by David Fincher, ensuring  a dark, gripping, and stylish story. Pitt plays the fresh faced but explosive Detective Mills, who is paired with Somerset (Freeman), a kind-hearted, soon-to-retire detective who has seen too many bad things in his career. They are tasked with stopping a serial killer whose murders are based on the seven deadly sins, but soon the duo find themselves more involved in the case than they would like to be. Pitt shines as a complex and flawed character, something that he would go on to master over his career and particularly in our number one slot.

 1. Fight Club (1999)

Playing Tyler Durden in the 1999 cult classic Fight Club enabled Pitt to play to his strengths; playing a good-looking and charismatic character who is also dark and complex. Pitt stars alongside Edward Norton, with both actors turning in powerful and career-defining performances, and the two form an electrifying dynamic which helps to make this a fantastic film. Norton plays the nameless main character and narrator, who meets Tyler Durden on a flight. Tyler is charming but anti-materialistic, leading the two to form the titular “Fight Club.” This later becomes “Project Mayhem”, an anti-corporate organization that commits domestic acts of terrorism, including a plan to destroy buildings containing credit card companies’ records. The narrator attempts to stop this, with the twisting story reaching a dramatic and enthralling conclusion. Another David Fincher film, Fight Club is thought-provoking as well as action-packed, and sees Pitt deliver his most famous line: “The first rule of Fight Club is – you do not talk about Fight Club.”