The 100 Greatest 2000s Movie Characters (60-51)

The 2000s. It was a time of bad fashion, worse music (nothing but boy bands and nu metal), and political strife but it wasn’t all bad. Television was entering its golden era with shows like The Sopranos; The Shield; The Wire and Six Feet Under, the internet was slowly becoming a major part of all of our lives and movies were getting better and better. The auteurs of the ’70s and ’80s were still cranking out masterpieces and the film brats of the ’90s were already inspiring damn fine copycats. Big budget spectacles shared theater space with no-budget indies and nostalgia hadn’t become omnipresent. It was a glorious time to be a movie fan. We were spoiled with good movies and even better characters. Characters that have lived with us for so long, that they make us forget that we first saw them over twenty years ago. The new millennium might’ve been a long time ago at this point but its films and the characters therein, haven’t aged a day.

These are the 100 Greatest 2000s Movie Characters.

60. Don Logan (Ben Kingsley) | Sexy Beast (2000)

I don’t think I’ve ever felt as anxious and uncomfortable when watching a movie as during the Don Logan scenes in Sexy Beast. Played by Sir Ben Kingsley, Logan is a small, aggressive, obsessive psychopath that is used to getting his way. When his old acquaintance Gal says no to his demands, things get spicy, to say the least. No matter how many times I watch Sexy Beast, when the sweat starts to drip from Don Logan’s brow and the veins pop out from his head, I have the urge to watch from behind the sofa.

–Lee McCutcheon

59. Sirius Black (Gary Oldman) | Harry Potter and the Prisoner of Azkaban (2004)

I honestly believe if you could make the Academy forget that the Harry Potter films were part of a billionaire-dollar fantasy franchise a lot of the older actors would have received Oscar nominations for their performances. I’m not saying everybody, but case in point, Gary Oldman acted circles around every other actor in 2004’s Harry Potter and the Prisoner of Azkaban as Sirius Black. Oldman perfectly brought the godfather of Harry Potter to life and although he only appeared in four movies (damn you Rowling for killing him off), he made the most of every scene he was in. Prisoner of Azkaban presents Sirius as a wild murderer, a lunatic and traitor out for revenge, who did his “waiting. Twelve years of it, in Azkaban!” However, once the truth comes out, Goldman is able to portray the more loving and fatherly figure the fans love and hold dear. I understand why Rowling had to kill Sirius Black in Order of the Phoenix, but dammit did I not want to see more of Oldman’s Sirius Black. A phenomenal actor bringing a fan favorite to life. What more could we have asked for?

–Marmaduke Karlston

58. Giselle (Amy Adams) | Enchanted (2007)

Enchanted is the type of film I wish Disney would still make these days (seriously, do they even release original live-action films these days that aren’t part of a brand/IP?). The film is both a parody of and a love letter to Disney classics, especially the films released during Walt Disney’s time, referencing everything from Snow White and Mary Poppins to Sleeping Beauty and Bambi.

However, despite the film’s cast (Patrick Dempsey, James Marsden, Timothy Spall, Idina Menzel, Rachel Covey, and Susan Sarandon) knowing exactly the type of movie they’re making, it is Amy Adams who deserves the most credit for making Enchanted work. Giselle could have easily come across as jokey and one-note, but Adams injected the character with actual heart. It’s a shame that the only reason Giselle isn’t an official Disney Princess is that Disney would have had to pay Adams to use her likeness forever on official merchandise because the character is probably the best princess for kids to have as a role model. Now excuse me while I run off and rewatch Enchanted again.

–Marmaduke Karlston

57. The Faun (Doug Jones) | Pan’s Labyrinth (2006)

Was the faun real? Does it matter? Doug Jones manages his magic, making the ethereal character both frightening and beautiful, something we want to trust – but that shouldn’t be trusted. When we first see the faun he’s decrepit, harmless, but as the film progresses – and the “real world” gets darker and darker – his appearance shifts, he becomes younger somehow, as if feeding off of Ofelia’s unhappiness. We remember how Mercedes tells her not to trust fauns. And yet, in the end… well. Guide, gatekeeper, friend and sometimes foe, the Faun is unforgettable, with a fantastic makeup design and the incredible Doug Jones bringing him to life. Even if he wasn’t real (and he was for me) he was unforgettable.

–Bob Cram

56. Donnie Darko (Jake Gyllenhaal) | Donnie Darko (2001)

So, let’s set aside the meaning of Donnie Darko and whether it makes sense or not. This is about Donnie the character, as played by Jake Gyllenhall in one of his earliest roles. Despite the craziness of the plot and details (like Donnie’s visions of Frank) the arc of Donnie himself is not unlike that of a typical John Hughes character. A societal outcast with a cynical view of life, but with a decent heart, struggles against a life that feels like it’s inevitable only to embrace the actions that will help those around him. While everyone feels like the world is against them sometimes, in this case Donnie is right – the world is trying to fix itself, and it will come at Donnie’s expense. Gyllenhal manages to make Donnie likeable, even when he’s giggling about the apocalypse, burning down a pedo’s house or even shooting a guy in a rabbit costume. Donnie’s nihilism turns into selflessness, but in a way that actually validates his earliest nihilistic thoughts. No wonder he laughs at the end of things. When the universe really is out to get you, that’s really the only sane choice.

–Bob Cram

55. Yu Shu Lien (Michelle Yeoh) | Crouching Tiger, Hidden Dragon (2000)

Entrusted to deliver the prized sword of her longtime friend (and secret lover) to his acquaintance, Yu Shu Lien then feels immense shame when it’s immediately stolen. In order to fulfill her oath and to regain some honor, she then embarks on an epic quest of Kung Fu fury to get it back. With Everything Everywhere All At Once making all the money right now, it’s insane to think that this was considered the twilight of Michelle Yeoh’s career. Apparently there’s an age limit placed on actress’s careers where they’re forbidden from kicking ass after 35. Yeoh clearly didn’t get that memo because she kicked all the ass then and she continues to kick ass over 21 years later. And she’s one of the only ones I can think of that can kick ass while having poise and grace. It’s a performance that reminds me a bit of an inverse Mifune. Where he was usually out of control and unpredictable, she’s measured and composed but they both have that je ne sais quoi that makes it impossible to take your eyes off them. They own the screen every time they’re on it. Yeoh’s presence is immediately captivating. She helps draw you into the world while anchoring it in real human emotion. I want her to get the sword back not because she feels duty bound or because it’s her job. I want her to get it back because she knows how much it means to her friend and his happiness means more to her, than her own safety. It’s a grand romantic gesture trojan horsed in a bunch of action. Which automatically makes her the best love story heroine ever.

–Sailor Monsoon

54. Walt Kowalski (Clint Eastwood) | Gran Torino (2008)

It’s hard to imagine this movie coming out today. Everything is black and white now. Cut and dried. We are all stereotypes. Unable to break free of whatever label has been placed on us by society. Whatever box has been ticked on our behalf.

But people aren’t really that simple. And human relationships aren’t that simple either. And that’s what Gran Torino is about. That’s what Walt Kowalski is about. At first, Walt seems like a caricature. He’s the old man yelling at you to get off his lawn. He’s got nothing better to do than be a grumpy old, racist asshole.

But behind that cartoon is a person with real feelings, real hurts, real hopes, real potential—a person capable of caring for and loving other people. Walt shows us that things aren’t black and white or cut and dried and that stereotypes break down once you look beyond the surface and get to know the actual human behind the label. I’m sure someone somewhere has decided that Gran Torino is horrible and awful for a variety of different reasons, but I think we could learn a lot from Walt Kowalski.


53. Robert Ford (Casey Affleck) | The Assassination of Jesse James by the Coward Robert Ford (2007)

If Jesse James is the realization of the mythical outlaw, then Robert Ford surely is the realization of the fanatic who idolizes the myth. A wide-eyed lover of all things fed to him by pulp and gossip, Casey Affleck’s Robert Ford is the embodiment of a fan who gets a peek behind the curtain. A cinephile, if you will, who discovers too much movie magic at play to the point of becoming disillusioned with it all. It isn’t enough that he’s infatuated with Jesse James, Ford all but emulates his hero. The young fan puts a tilt to his hat, attempts a swagger that would never come naturally, and ultimately takes on the depressive personality when the magic fades. Once he becomes disillusioned with the godlike persona, discovering a man, cruel and petty and incapable of living up to the legend, Robert Ford seeks to carve out his own bit of fame by way of taking down his hero, by killing the myth. Only with the deed done, and garnering his own bit of notoriety, does he find himself truly in the shoes of his former hero: isolated and alone, high on his own pedestal. It’s all a remarkable trajectory and characterization that can easily go overlooked, but there is a sort of pathetic bit of pathos that oozes from the naïve Robert Ford that flows freely when the hero-worship disappears and he himself can’t cope with the realities in place of the stories.


52. Leonard Shelby (Guy Pearce) | Memento (2000)

“How am I supposed to heal if I can’t feel time?” I’m a sucker for identity stories, particularly ones involving amnesia. Is who you are simpy a result of all your experiences? Or is there something else, a deeper core to your personality that would assert itself, even in the absence of those particular moments? Would you, in fact, be a better person without all of that baggage? Or a worse one? The thing about Leonard, played with grace and heart by Guy Pearce, is that he doesn’t have that sort of amnesia. Instead, he has anterograde amnesia – the inability to form new memories. He can’t really remember much since the death of his wife. But the the notes he’s written – and the tattoos on his body – document the search for the man who killed her. The narrative structure of the film as written by director Christopher Nolan from a story by his brother Jonathan, unfurls both backwards and forwards in time as we learn why Leonard has killed a man and how he came to that point. We also learn about Leonard and how his heart is broken every day. He knows his wife is dead, but no time has passed since that moment. Revenge is something that often occurs to someone when a bad thing happens to them, but time blunts that rage. Leonard doesn’t have that luxery. He can’t make new friends, or watch new films or heal his heart. We want him to, though. We want to so badly that even the ending can’t turn us against him. We don’t want to believe what Teddy (Joe Pantoliano) says – and after all, Leonard keeps a photo of the man that says “don’t believe his lies” on the back. I don’t want Leonard to be any more hurt and broken than he already is. That’s how well Guy Pearce makes us feel for him.

–Bob Cram

51. Bryan Mills (Liam Neeson) | Taken (2008)

“I don’t know who you are. I don’t know what you want. If you’re looking for ransom, I can tell you I don’t have money but what I do have are a very particular set of skills. Skills I have acquired over a very long career. Skills that make me a nightmare for people like you. If you let my daughter go now, that will be the end of it. I will not look for you, I will not pursue you. But if you don’t, I will look for you, I will find you and I will kill you.”

Has there ever been a more quotable line from an action film than the one Liam Neeson’s Bryan Mills says to the men that took his daughter? The actor, who rose to prominence with his acclaimed starring role in Schindler’s List, had mostly built a career out of dramatic performances in more serious fare than the average blockbuster film. Beginning with 1999’s Star Wars: Episode I – The Phantom Menace, Neeson started to take on roles that would reach a wider audience, appearing in Christopher Nolan’s Batman Begins and The Chronicles of Narnia adaptations. However, Taken by far had the biggest impact on his career. The audience had seen action protagonists like Bryan Mills before, but what they hadn’t seen was Liam Neeson embodying that character. There’s a reason Neeson has primarily starred in action films since Taken was released. The man does a great job of humanizing the grizzled and/or broken men he portrays and that’s thanks to his early theatre background and spending the first two decades of his career honing his craft with dramatic roles. Neeson’s Bryan Mills is all business and if he comes knocking at your door, it’s best you just do what he says.

–Marmaduke Karlston

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What do you think of the selection so far? Who are some of your favorite 2000s characters? Maybe they will show up further on the list!