In a recent interview with The Sunday Times, actor Gary Oldman confessed that he is ready to end his legendary career. "I’ve had an enviable career, but careers wain, and I do have other things that interest me outside of acting,” he told them. “I’m 65 next year, 70 is around the corner. I don’t want to be active when I’m 80. I’d be very happy and honored and privileged to go out as Jackson Lamb — and then hang it up," Oldman continued, referring to his character in his Apple+ series, Slow Horses, which debuted this past April.

Oldman’s long career has remained relevant due to the particular roles he takes. He can take the lead in an independent film or play a supporting role in a giant blockbuster. He’s a chameleon that can go back and forth between being the hero and the villain. If this is truly the end of such a distinguished acting career, then these are the essential roles that fans should never forget.

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Sid Vicious in ‘Sid and Nancy’ (1986)

Gary Oldman has had a knack for being able to get under the skin of real-life figures. He first developed this by playing the tragic bass player for the 70s punk band The Sex Pistols. This film tells the story between Sid Vicious (Oldman) and his girlfriend Nancy Spungen (Chloe Webb), the latter of whom was stabbed to death, leading to Vicious being arrested for her murder. It’s a chaotic film, with Oldman channeling Vicious’ frenzied nature, leading to a heartbreaking conclusion. Oldman had done some small roles before this, but the prominence of such a popular true story got the attention of movie fans and Hollywood alike, changing Oldman’s career forever.

Lee Harvey Oswald in ‘JFK’ (1991)

Again, we get Oldman playing a real-life personality, this time as John F. Kennedy’s assassin in this film from Oliver Stone. Say what you will about the film’s controversies surrounding its accuracy, but Oldman becomes Oswald, nailing his body language and eccentricities perfectly. While the film would be nominated for numerous Academy Awards, Oldman wouldn’t be recognized. His mastery at playing some of reality’s most disturbed minds may have made him a favorite with fans and directors, but it appeared to have made the Academy uncomfortable for decades.

Dracula in ‘Bram Stoker’s Dracula’ (1992)

While not a real-life person, Oldman taking on the role of Dracula was even more tricky, seeing as how it had been made so famous by the likes of Bela Lugosi and Christopher Lee. Oldman succeeds by playing Dracula completely differently from what we’ve seen before. We don’t get slick-backed hair and capes, but two drastically presented forms, with one as Oldman as a very old man with white hair, and the other as a Dracula with long hair, mustache, glasses, and a hat. It could’ve been silly, but with Oldman, director Francis Ford Coppola, and the Oscar-winning team behind the makeup and costumes, Dracula becomes a different beast without being a clone. Oldman comes across as tremendously scary, while also sexy and captivating.

Drexl Spivey in ‘True Romance’ (1993)

This bizarre film, directed by Tony Scott and notable for being written by a young Quentin Tarantino, is led by a well-known cast with the likes of Christian Slater, Patricia Arquette, Dennis Hopper, Val Kilmer, Christopher Walken, and Brad Pitt. Oldman may have been a bit behind the others in star status, but he steals every scene he’s in as a crazed drug-dealing pimp you don’t want to run into. As he so often does, Oldman fades into the character, this time behind scars, a milky eye, and dreadlocked hair. He’s cool but cunning, a badass but brutally violent. In the end, he leaves us with one of the best film villains of the 1990s.

Stansfield in ‘Leon: The Professional’ (1994)

Oldman masters the art of playing an unforgettable villain once again as an insane, drug-riddled psychopath opposite a young Natalie Portman in her first movie role, and Jean Reno as the titular character in this Luc Besson film. After Portman’s character of Mathilda sees her family killed by Oldman’s Stansfield, she ends up in the care of Leon, an assassin. They then team up to take down Stansfield. Oldman plays a sadistic criminal capable of anything, a mind so despicable that when he finally gets his comeuppance, it’s one of the most satisfying bad guy deaths you’ll ever see.

Zorg in ‘The Fifth Element’ (1997)

Three years later, Oldman would reteam with Luc Besson for a strange sci-fi film that could have gone off the rails and become a complete disaster if not for the performances of Bruce Willis, Milla Jovovich, Chris Tucker, and Oldman. It’s a movie that’s not for everyone, but it earns its cult status as one of the 90s most delightfully peculiar films. Oldman shines by playing the villain yet again. He’s like a cheesy cartoon come to life, but in a fun way, and never in a way that mocks the movie or diminishes the story. In a film with bizarre effects and wardrobes, Oldman is the most over-the-top but successful aspect due to his ability to lean into the zaniness.

Ivan Korshunov in ‘Air Force One’ (1997)

Oldman gets his chance here to play a more traditional, but still, equally frightening 90s action villain in this Harrison Ford-led film that sees the President’s plane hijacked by terrorists. You would be wrong if you went into this one dismissing it as just “Die Hard on a plane.” This is an underrated film not just for Ford, but Oldman. Oldman digs into the stereotypes of other Russian action movie villains and turns into something familiar but also new. Coming off of the heels of The Fifth Element in the same year, Oldman now had two hits in a row that had pushed him beyond being a great character and into becoming a household name.

Sirius Black in ‘Harry Potter and the Prisoner of Azkaban' (2004)

Oldman’s most popular and most anticipated role would have to be this one. The Harry Potter films were monstrous hits in the early 2000s, and this third entry promised that Oldman’s newly introduced character of Sirius Black was a big deal simply from the title. The role was a risky one, with millions already having forged the character in their mind through the best-selling books, but Oldman manages to tap into the material in a way that gives you what you expect but with his own characteristic spin. This more character-oriented film brought in Black as Harry’s godfather. His nature as someone both good but pulled in by the dark was the perfect material for Oldman, who brought out the best in his young cast mates. He would appear in other Harry Potter films, but this one gave him the biggest spotlight.

Jim Gordon in ‘The Dark Knight Trilogy’ (2005-12)

Just as big as stepping into the world of Harry Potter was stepping into the deeply woven world of Batman. There had been so many incarnations of Jim Gordon over the years in film, animated series, and comics, but Oldman’s version became the most memorable. There’s no villainous side to Oldman here. He plays Gordon as a serious man, but one who believes in good and will fight to protect it, even when it comes to helping a vigilante. He was the perfect police sidekick to Christian Bale’s Dark Knight. When we thought he died in The Dark Knight it was tragic, but when he rose again to arrest the Joker, it was one of the franchise’s big-crowd favorite moments. In a world of chaos, for once, Oldman wasn’t the one causing it, but the stoic center trying to keep everything from unraveling.

George Smiley in ‘Tinker Tailor Soldier Spy’ (2011)

For decades, the Academy Awards ignored Oldman’s contributions to film, but finally, after years of thrilling audiences, Oldman got his first nomination for this spy thriller set during the Cold War. Based on the classic novel by John le Carré, Oldman leads a heavyweight cast including Colin Firth, Benedict Cumberbatch, and Tom Hardy, Oldman plays George Smiley, a British intelligence agent who has to come out of retirement to catch a Soviet double agent. It was a challenging role, but one that Oldman makes his own, rather than copying from the past. (Alec Guinness' performance in the TV series over thirty years prior is still iconic.) He proved that he had become not just one of Hollywood’s best actors, but one of its best leading men as well.

Winston Churchill in ‘Darkest Hour’ (2017)

Oldman got his second Oscar nomination and a win for Best Actor for playing Winston Churchill in Darkest Hour. The film follows the Prime Minister in the spring of 1940 during the early days of World War II. A lot of credit goes to the phenomenal makeup team that transformed Oldman so seamlessly into Churchill, but this performance goes way beyond an actor in makeup. He turns Churchill into a three-dimensional person, rather than the heroic and simplistic character he’s often seen as, all without trying to mimic him. The performance works by not giving us a bland hero but a real man.

Herman Mankiewicz in ‘Mank’ (2020)

Oldman got a third Oscar nomination for once more nailing the portrayal of a real-life person. Everyone knows who Winston Churchill is, but perhaps even more challenging is becoming someone that so few know about. Oldman gives a multifaceted performance as a screenwriter whose life is falling apart by his own doing as alcoholism slowly destroys him. This is not a film that stays in sad tropes of the fallen, however, for it’s also one about perseverance. Oldman’s character, Herman Mankiewicz, wrote Citizen Kane, but he had to deal with the cruelty of Hollywood along the way as he tried to save his screenplay. It’s an insightful look into the dark side of filmmaking and gives us a character who’s not always the most likable, but due to Oldman, whose side you will stay on.