The 100 Greatest 2000s Movie Characters (50-41)

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.

50. Mary Margaret “Maggie” Fitzgerald (Hilary Swank) | Million Dollar Baby (2004)

“I was born two pounds, one-and-a-half ounces. Daddy used to tell me I’d fight my way into this world, and I’d fight my way out.”

Maggie Fitzgerald is a fighter. She grew up in utter poverty born into a family of trash. Her life is nothing but a series of obstacles she’s had to endure and overcome. Because of (or perhaps in spite of) that, she has just one dream: to become a boxer. It’s a dream she’s had for a very long time and she’s finally going to pursue it. Problem is, she’s a dish washer with zero experience who’s far too old. But she’s used to obstacles. Nothing is going to stand in her way. Not even the legendary trainer Frankie Dunn (Clint Eastwood) when he tells her that he doesn’t train girls. Not even when she finally wears him down and gets him to train her and he still tells her she’s no good. Not even when he gets her some fights and the other girls beat the shit out of her. She keeps going, keeps fighting. Until the end when she decides to finally stop fighting and it’s one of the most soul crushing moments in film. Her dream may not have happened just the way she wanted it to but there’s no denying she died a true fighter.

–Sailor Monsoon

49. Enid Coleslaw (Thora Birch) | Ghost World (2001)

Ghost World takes place in a world of weird but relatable characters. Every person that inhabits this world feels slightly off, like they’re all flesh and blood comic book characters adapted from some obscure hipster graphic novel. Well, that’s because they are and they did. Daniel Clowes is about as niche a writer as they come and while Ghost World is one of his more accessable comics, it’s still not mainstream in anyway. The man writes about weirdos living eccentric lives doing mundane things. That’s exactly what this movie is and that’s why it works. Nothing else feels like this movie. It has it’s own vibe as the kids say. It’s like Wes Anderson directed Napoleon Dynamite but with no money and a lot less awkward cringey quirk. I mean, the name Enid Coleslaw is not that far off from Napoleon Dynamite but that’s about where the similarities end. She’s an 18-year-old cynic who thinks she knows everything and looks down on those she thinks haven’t figured “it” out yet. Suffice it to say, her friend circle is very small. There’s her age appropriate best friend and her second best friend who’s considerably older and far more introverted. He’s a socially awkward album collector she clicks with for some reason. It started off as a lark but the more she talks to him, the more she connects with him. She’s never fit in with people her own age, so a creepy ass Steve Buscemi as a hangout buddy makes about as much sense as anything else she does. She’s just trying to find her way in life and right now, she’s just enjoying her time at this weird metaphorical (and later, literal) bus station until she can move onto her latest adventure.

–Sailor Monsoon

48. Chow Mo-wan (Tony Leung) and Su Li-zhen (Maggie Cheung) | In the Mood for Love (2000)

I’ve got a soft spot for movies about people not getting what they most desire. Mac wishing he could trade places with Gordon and stay in Ferness with Stella in Local Hero or Guy and Girl falling for each other but realizing it can never be in Once—both of these movies leave me feeling melancholy, but at least that’s something real. And maybe that’s what appeals to me about these kinds of movies and these kinds of characters.

In the Mood for Love is one of those movies. Chow and Su’s budding relationship feels so real throughout the entire length of the film. There’s never a time in the whole movie where these two people don’t feel like whole humans. They meet, have no real reason to be friendly, but as it dawns on them that their spouses are having an affair with one another, the two grow close and eventually fall in love. But it’s not to be, and the movie ends on a note that is not that different from that final shot of the red phone booth and the ringing phone that goes unanswered in Local Hero. It’s enough to make a grown man weep, and it’s enough of a reason to include Chow and Su on this list.

–Billy Dhalgren

47. Eli (Lina Leandersson) | Let the Right One In (2008)

Eli doesn’t want to be friends. Eli doesn’t know when their birthday is. Eli doesn’t smell so good. Eli needs blood to live and needs to be invited in. Eli is a vampire, and they’re not really sorry about it. The first time I watched Let the Right One In… (Tomas Alfredson’s adaptation of John Ajvide Lindqvist’s novel) I remember wishing I’d had a friend like Eli when I was Oskar’s age. A time of my life filled with upheaval and bullying. Eli, after all, supports Oskar and even defends him – albeit in an ultraviolent way (that pool scene is still fantastic). They bond over a shared sense of isolation and alienation.

The last few times I’ve watched the movie, however, I’m very aware of how old Eli is. How many times they’ve had to do this particular dance. Of how their caretaker, Håkan, may well have started off exactly like Oskar. How Oskar would now (in 2022) be approaching Håkan’s age and how maybe Eli would be starting to think about befriending another child… (I wouldn’t say no to a sequel.) And yet, I still feel for them, still want Oskar and Eli to be friends. Eli is a monster, but they have loyalty, they have a need for friendship, they have the ability to give and receive trust and love and understanding. Or at least that’s what Lina Leandersson’s performance indicates. I don’t know that all of my childhood friends turned out to be good people, but I’m still glad I had them. And I would still have lent Eli my Rubik’s cube.

–Bob Cram

46. Royal Tenenbaum (Gene Hackman) | The Royal Tenenbaums (2001)

If Hackman had retired here, he’d have about as good a send off as any actor could dream of but he decided to keep working another three years producing shit like Welcome to Mooseport, Runaway Jury and Behind Enemy Lines (which I actually like.) Not only is this one of his best performances but it might be Wes Anderson’s finest creations. He’s not as funny as some or as memorably eccentric as others but few are as complex. He’s a piece of shit with almost no redeeming qualities who is as bad a husband as he is a father. He’s like a ghost who haunts his own family who comes back into their lives years after they exercised him. All but one of his children are upset with his arrival and they want anything to do with him but since he’s the one that fucked them all up in the first place, it feels appropriate that he’s the one to fix it. But in true Wes Anderson fashion, he even fucks that up. He has an emotional connection with his eldest son and gives him a space to feel vulnerable, and in the process, helps him unload some emotional baggage he’s carrying but other than that, he almost makes everything worse. And yet, because it’s Hackman, you can’t help but love the son of a bitch.

–Sailor Monsoon

45. Miranda Priestly (Meryl Streep) | The Devil Wears Prada (2006)

The lady boss of all lady bosses. Played to perfection by Meryl Streep, Miranda Priestly is demanding (almost irrationally so), blunt and terrifying as the Editor in Chief of fashion magazine, Runway. She is arguably one of film’s greatest villains, not only due to her intimidating, disparaging behavior but because she is also shown to be complex thanks to moments of vulnerability that shine through the icy exterior. She is the kind of character that you love to hate and even when you’re grimacing at her judgmental stares and sharp retorts, you still can’t help but be impressed by her as well. While The Devil Wears Prada revolves around the evolution of Anne Hathaway’s Andy Sachs, it’s truly Miranda’s movie.

–Romona Comet

44. Mike Wazowski (Billy Crystal) and James P. “Sulley” Sullivan (John Goodman) | Monsters, Inc. (2001)

Mike and Sully certainly have one of Disney’s greatest animated friendships. The two meet at Monsters University and end up as workers in the mail room at Monsters, Inc. We all know what happens from there. Voiced by Billy Crystal and John Goodman, Sully and Mike are two very different monsters who approach situations in completely different ways, but you never doubt their loyalty to one another. Sully is the brawn and Mike is the brains and the two simply do not work without the other. They’ve certainly endured as two of Pixar’s most popular and most beloved characters, getting a prequel (Monsters University) and also a Disney+ series called Monsters at Work, where Mike and Sully occasionally make an appearance.

–Romona Comet

43. Dobby (Toby Jones) | Harry Potter and the Chamber of Secrets (2002)

I was late to the party with the Harry Potter franchise. It just looked like some silly shit to me. Emblematic of that silly shit is Dobby the house elf. I remember seeing the character in trailers and then catching snippets of the movie during holidays when family would be watching the movies, and what I saw annoyed the hell out of me.

Well, eventually, on another one of those holidays, I ended up sitting down and watching the first movie. And then I read the first book. And then I read all the books and watched all the movies, and at this point, I would say that I am a fan of the franchise (not a big enough fan to watch those shitty-looking prequels, though). But I’m still not a fan of Dobby the house elf.

First off, it’s just a terrible design. The character is ugly. Why not make him cute? Or at least ugly-cute like Yoda. And on top of that, they made the little fucker so annoying. It’s like the filmmakers saw The Phantom Menace and decided to use Jar Jar as inspiration for Dobby.

Dobby is a terribly-designed character from the aesthetics to the personality. And I wish Harry would never have given him that sock.

–Billy Dhalgren

42. Alan Garner (Zach Galifianakis) | The Hangover (2009)

What can I say about Alan? He’s a dumbass. An absolute dumbass, but gosh darn it he’s a lovable dumbass. He’s the brother-in-law no one wanted at the bachelor party and yet he HAS to be there. He’s the brother-in-law to the guy who is barely in the movie. And on top of it, he’s the cause of all their problems in the film because he’s a dumbass.

Alan idolizes Phil (Bradley Cooper) like you wouldn’t believe and mimics him as much as he can. And I get it, Phil’s a dick, but a charismatic dick. And besides Alan doesn’t know any better, he’s like a child. He never curses (minus two times) and he’s always laid back like he doesn’t have a care in the world. I don’t know what else to say, Galifianakis just nails the Alan character 100%.

–K. Alvarez

41. Randy “The Ram” Robinson (Mickey Rourke) | The Wrestler (2008)

Whether you are a fan of professional wrestling or not, everyone should watch The Wrestler. Mickey Rourke stars as aging wrestler Randy the Ram. Wrestling is all he has known throughout his life and when his body starts to let him down, he tries his best to come to terms with the reality of his situation. As he gets a job in a deli, tries to reconcile with his daughter, and explores how to lead a normal life, you can’t help but empathize with him. He’s made many mistakes but at heart seems like a good person desperately seeking redemption. A complex character and the whole reason the film works.

–Lee McCutcheon

60-51 | 40-31

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!