The 100 Greatest 2000s Movie Characters (90-81)

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.

90. Nick Naylor (Aaron Eckhart) | Thank You for Smoking (2005)

There are certain performances I’m shocked didn’t catapult their actors into the A list and Aaron Eckhart in Thank You for Smoking is one of them. It got him the role of Harvey Dent in The Dark Knight but other than that, it doesn’t seem like his phone has been ringing off the hook and I honestly can’t understand why. 2005 was a helluva year for leading actor performances, so I can understand why he got overlooked a nom but I feel like the Academy still would’ve snubbed him regardless. It’s the type of performance they never know how to award. He’s funny (which they hate) but he’s also dramatic (which they love) but the film is funny (which they hate) but it’s also darkly satirical (which they love) and their heads just exploded. They like easy characters they can put in a box because it’s easier for them to classify but Nick Naylor can’t be and won’t be put in no box. He’s a fast talking tobacco lobbyist with loose morals who loves his son but also loves his job. He’s very good at debating people with double talk, fancy words and shaky logic. He takes pride in the fact that he can convince almost anyone of anything, a skill he even tries to pass on to his son. But after his life is threatened and the carefully built house of cards he helped build starts to topple, he starts having a change of heart. It’s a character arc that doesn’t go exactly where you think it would because deep down inside, you don’t really want to see him change. Watching him demolish opponents with his words alone is as entertaining as any fight scene. He’s a scum bag working with the Devil but because Naylor is so charismatic, you want him to never stop. He’s a lovable piece of shit you’re almost rooting for. It should’ve done for Eckhart what Iron Man did for Robert Downey Jr. Which, coincidentally also wasn’t nominated. Get your shit together Academy.

–Sailor Monsoon

89. David / Tsotsi (Presley Chweneyagae) | Tsotsi (2005)

On the film’s poster, there are two taglines — “Hope Set Him Free” and “In This World… Redemption Just Comes Once” which tells you all you need to know about this movie. Based on context clues, it’s safe to assume that the film is about someone needing to atone for either one major sin or a lifetime of crime and that they only have one shot at it. That’s basically Tsotsi in a nutshell but a more accurate tagline would be “Does Everyone Deserve Redemption?” After accidentally killing someone during a robbery gone bad, Tsotsi, a gang leader located in the slums of Africa, ends up with a three month old baby. Realizing it’s his one shot at redemption, he does everything in his power to take care of the baby until the time is right to return it but complications keep rearing their ugly head. Since a life of crime is all he knows, taking care of an infant is as alien to him as reading Mandarin but with his conscience eating away at him, he’s forced to grow as a person. He now has a purpose in life and it’s to give this baby a better life than he ever had. It’s a simple story grounded by an incredible lead performance. Chweneyagae adds layers of complexity to a clichéd character we’ve seen a million times before. His eyes are the film’s secret weapon. There’s a lifetime of hard living, bad decisions and deep sadness behind them. I have no idea what the actor was pulling from to give this performance but I hope it wasn’t anywhere near as bad as what Tsotsi goes through.

–Sailor Monsoon

88. Vincent (Tom Cruise) | Collateral (2004)

Remember that time in Tom Cruise’s career when he allowed himself to be at the whim of a great director? That was fun. All the praise to Michael Mann for giving us Cruise at his most sinister. It’s always fun when actors play against type. But it’s especially fun when the quintessential Hollywood leading man takes on a role as a cold-blooded killer. As he lurks in the back seat of the cab, Vincent instills a palpable sense of fear in both Max (Jamie Foxx) and the audience alike. Cruise’s Vincent feels equal parts precisely calculated and completely unhinged – and that’s what makes him so amazing to watch.

–Raf Stitt

87. Willie T. Stokes (Billy Bob Thornton) | Bad Santa (2003)

A mall Santa during the day and a safe cracker at night, Willie uses the cover of his temporary gig to do some reconnaissance and while that’s all well and good, there’s one major problem with his plan: he’s a hardcore alcoholic. He’s a short-tempered, mean-spirited lush who berates and/or fucks everyone he meets. He’s as vile and hateful as the Grinch and antisocial and loathsome as Scrooge but without the greed. Which makes his eventual redemption all the more powerful.

In addition to his mall shenanigans and drunken escapades, he also builds a friendship with a weird kid named Thurman Merman. At first he can’t stand him, but over time, the kid’s odd eccentricities start to rub off on Willie and soon he’s beating up other children who bully him and he even steals him a pink stuffed elephant. It’s not as big a gesture as saving Christmas or buying a cripple kid a turkey but seeing as how Willie is one of cinema’s biggest assholes, it’s a big deal.

–Sailor Monsoon

86. J. Jonah Jameson (J. K. Simmons) | Spider-Man (2002)

Has there ever been a better casting choice in the history of comic book cinema than JK Simmons as J Jonah Jameson? Every scene in Raimi’s Spider-Man trilogy that features the J. Jonah Jameson character is filled to the brim with fantastic kineticism. Simmons brings an energy that matches Raimi’s campy yet heartfelt interpretation of the Spider-Man story. While many of his most memorable moments feature top-notch comedic wit, J Jonah Jameson shines brightest when his emotional side gets time to shine.

–Raf Stitt

85. Nikolai Luzhin (Viggo Mortensen) | Eastern Promises (2007)

Wedged somewhere between Jodorowsky’s Dune, Giraffes on Horseback Salad (an insane collaboration between The Marx Brothers and Salvador Dalí) and Christ Killer: Gladiator 2 is Eastern Promises 2, one of the greatest unmade movies ever. While I think it stands alone and doesn’t really need a sequel, there’s a ton of potential for a trilogy because they was always the goal. Cronenberg never intended Nikolai Luzhin to be a one and done character. We were going to follow his rise within the Russian mafia while dealing with life as an undercover agent. It’s played as a twist at the end of the first movie but that was supposed to be but a tease for a much more expanded role in the sequel. That, along with the Mafia storyline, could’ve produced one of the all time great crime epics but since it was cancelled, it’s now just one of the best films of the decade and amongst Cronenberg’s best. Since he’s an enigma who’s impossible to read, Luzhin demands more screen time. I would love to see which side he’s more involved in or which side he pledges more allegiance to. Is there an internal conflict or is he playing both sides against the middle. I have no idea and I kinda love that. As much as I’d love a sequel (it’s not too late Cronenberg!), I love that I’m forced to answer the questions myself and I don’t want to. I like the fact that he’s a mystery. But man, I really would’ve loved to have seen him methodically take out each crime lord so that he can get to the top to either take it over or tear it all down. Goddamn it I want a sequel.

–Sailor Monsoon

84. Clementine Kruczynski (Kate Winslet) | Eternal Sunshine of the Spotless Mind (2004)

Clementine is a flawed character. She is moody, irrational, and just feels incredibly real. Eternal Sunshine is a fantastic film all around but it’s centered around its two main characters. Without their chemistry, it just wouldn’t work. As the characters fall in love, out of love, and everything in between, you don’t know if you want them to stay together or never see each other again. That’s down to the complexity of its leading duo and in particular, Clementine, who is my favorite thing about one of my favorite movies.

–Lee McCutcheon

83. Zé Pequeno / Lil Zé (Leandro Firmino da Hora) | City of God (2002)

A character so evil, they could make a list of the best villains twice. Once as a kid and the other as a young man because, while not drastically different in behavior, the two have vastly different types of motivation driving their crimes. The boy murders anyone he sees indiscriminately with the slightest provocation. He kills because killing is fun. He’s not doing it for fame or profit, he simply enjoys the act of murder. His systemic slaughter of an entire hotel is arguably the single most cold-blooded act any child has ever committed on film. If Rhoda Penmark is considered a “bad seed” for killing a couple of kids for shoes and trophies, Lil Zé is a bad orchard.

And that’s just flashbacks. His time as a kid is less than 20 minutes of the film. The bulk of the film is Lil Zé as a young man and with age, comes maturity. Gone are the days of being a homicidal loose cannon and in its place, the days of being a homicidal loose cannon but with ambition. He still kills anyone he wants but now he has a goal: to take over the titular City of God.

Fun Fact: this film is based on a true story.

–Sailor Monsoon

82. Mickey O’Neil (Brad Pitt) | Snatch (2000)

Brad Pitt would have been the last person I expected to play the part of an Irish traveller and bare knuckle boxer in a Guy Ritchie movie. The accent needed is an unintelligible version of English in a thick Irish accent, but it proved no problem for Pitt. His character Mickey O’Neil loves his fighting, caravans, hare coursing and whiskey, but loves his mother even more. When his story comes full circle it’s a thing of beauty, and even though it’s a relatively small part, it displays some of Brad Pitt’s best character work.

–Lee McCutcheon

81. Stitch (Chris Sanders) | Lilo & Stitch (2002)

Created by the mad scientist Jumba Jookiba for reasons unknown, Experiment 626 (also known as Stitch) is a small blue, koala-like space creature who’s primary function is annihilation. He’s bulletproof, fireproof, and can think faster than a supercomputer. He can see in the dark, and lift objects three thousand times his size. He’s the ultimate weapon of destruction and he’s running loose on the island of Hawaii. But since this is a Disney film and not another sequel to Critters, his destructive impulses are kept in check by an adorable little girl named Lilo. She teaches him about the joys of Elvis and the importance of ‘ohana – the Hawaiian term for family. Her love and acceptance of him, rewrites his programming and changes him from a monster, to a member of her family. He’s more than just a tool of destruction and he’s more than just a deformed pet, he’s family.

–Sailor Monsoon

100-91 | 80-71

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!