Today, I woke up to the sad news that terrific actor and by all accounts lovely human being Alan Rickman had died at the age of 69. Even though he was never ubiquitous, Rickman was such a foundational feature of American cinema that perhaps we took him for granted in some way. He was the charming jerk we could always count on, and he brought tremendous gravitas to every role he played even if he knew the role itself was beyond silly.

It’s incredibly difficult to pick out Rickman’s “best” performances because he, like any true actor, was incredibly generous. He did what he could to best serve the overall film. It wasn’t about stealing every scene or making sure he got the juiciest moments. It was about finding something unique in the character, and making it unforgettable. He didn’t need to chew the scenery to do it, but he was always game for whatever was required. It gave him tremendous range and always made him a welcome presence.

Here are five of his best performances in a career filled with wonderful work.

Hans Gruber, ‘Die Hard’ (1988)

Even though Hans is a thief and a murderer, it’s hard to root against him when he’s so charming. Rickman, who said he didn’t see Gruber as a villain but just as a person who wants something, plays the role so effortlessly. He’s in complete control of every single situation, and even when he gets a little ruffled, you can see him re-calibrate. You can tell Rickman is having a blast with the role (I love the little smile he gives Takagi when he tries to make small talk about their suits), and he really goes for it when he pretends to be “Bill Clay”.

But what’s most important about the performance is that he understands that the villain has to be as formidable as the hero, and one of the reasons Die Hard has endured is that Gruber—who not only represents a polar opposite personality than McClane—is a worthy adversary. Rickman creates that worth.

Sheriff George of Nottingham, ‘Robin Hood: Prince of Thieves’ (1991)

Unlike Die Hard, Robin Hood: Prince of Thieves is not a good movie. It’s an incredibly silly movie, but the only person who seems to realize it is Rickman. Maybe that’s because he’s part of a wacky subplot involving his witch/mother Mortianna (Geraldine McEwan) (you can see these scenes awkwardly integrated in the extended edition), but he’s the only actor in the film who seems to understand that the more director Kevin Reynolds tries to modernize the tale of Robin Hood, the more detached it becomes from reality.

So instead, he wisely leans into Nottingham being a cartoon rather than a three-dimensional, terrifying personality. Other actors would probably crumble under dialogue that has to explain the viciousness of cutting out a person’s heart with a spoon, but Rickman’s delivery made it the most quotable moment of the movie. Robin Hood: Prince of Thieves can be passably entertaining outside of Rickman, but whenever he’s on screen, it’s genuinely fun.

Colonel Brandon, ‘Sense and Sensibility’ (1995)

While Rickman will likely be remembered mostly for his villainous roles, he could also do nobility. In Ang Lee’s Oscar-winning adaptation of Jane Austen’s novel, Rickman plays Colonel Brandon, an old bachelor who falls for Marianne Dashwood (Kate Winslet), but harbors a painful past that he keeps a secret until he eventually chooses to confide in Marianne’s wise older sister, Elinor (Emma Thompson).

Even though no one could do a sneer quite like Rickman, his performance as Brandon shows the depth of kindness and quiet humility he could bring to a performance when called for. While everyone is terrific in the movie, he gives a lynchpin performance that makes us cheer at the end for all the good characters involved.

Alexander Dane, ‘Galaxy Quest’ (1999)

By this point in his career, Rickman would have been acutely aware of an actor’s living nightmare: to only be associated with one role and letting that blind you to the joy of acting. Galaxy Quest is an absolutely inspired film, and Rickman is an essential piece of the puzzle as Alexander Dane, the member of the short-lived eponymous sci-fi show who believes he’s too good to keep doing fan conventions and reciting his character’s signature line “By Grabthar's hammer, by the suns of Worvan, you shall be avenged.”

But Rickman also has the insight to play to Dane’s more vulnerable moments, not just the comical frustrations. Dane isn’t a riff on Leonard Nimoy (if anything, he’s sending up fellow British stage actors who think they’re too good for sci-fi comedy). He understands what Galaxy Quest is trying to do on the whole, and that understanding allows him to hit both the comic beats and the emotional ones with equal precision.

Severus Snape, ‘Harry Potter and the Deathly Hallows: Part 2’ (2011)

While I was tempted to simply list the Harry Potter franchise as a whole, it really isn’t until Harry Potter and the Deathly Hallows: Part 2 that Rickman gets to put a beautiful capper on the character. Until then, he had to be patient with Snape. He couldn’t turn him into a one-dimensional buffoon, but he did have to sit on the sidelines a bit. Until Half-Blood Prince, Snape is merely a thorn in Harry's side. There are some telling moments along the way (such as the occlumency lesson), but he’s mostly an occasional nuisance to Harry and he has to get out of the way until the plot.

But Rickman stuck in our minds just enough that when it came time for Snape's big reveal, everything fell into place. Because the character was never one-note, we could buy him as a well-rounded person, and Deathly Hallows: Part 2 gets to show us that deeply damaged person who may have been rotten to his core if not for his deep, undying love for Lily Potter.

Rickman walked this line beautifully. His dying wish to look in Harry’s eyes is gut-wrenching, and I fully agree with fans that Rickman should have been nominated for Best Supporting Actor (look at that year’s nominees and he deserves it more than everyone except the person who won). However, his work will live on regardless of Academy recognition. Alan Rickman played some of our most memorable characters, and keep in mind that I’m not even going into his prolific stage and TV work.

He was the villain you could root for, the reserved hero behind a cold exterior, and so much more.  Rest in Peace.