The 100 Greatest 2000s Movie Characters (70-61)

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.

70. Shaun (Simon Pegg) | Shaun of the Dead (2004)

Rom-zom-com Shaun of the Dead is SO good, so much fun and it works every level it aims for. Much of that has to be down to Simon Pegg – both as co-writer and as the titular character. Embodying the perfect (or imperfect) mid-life slacker, Shaun is a lost soul without ambition or focus, but with a good heart. He just can’t seem to find a reason or the energy to change his life, despite losing his girlfriend, having a shitty job, and not getting along with his stepdad. Usually in a romantic comedy there’ll be some inciting incident to spur our hero on to becoming a better version of themselves, and Shaun of the Dead is no different – it just happens to be a zombie apocalypse that makes Shaun step up, shake off his lethargy and move forward with his life. Like any good RomCom it’s the relationships that make or break the film, and here Shaun’s friendship with Ed (Nick Frost), his romance/breakup with Liz (Kate Ashfield) and even his antagonism with his stepdad (Bill Nighy) all work and ground the film. If I say I saw a little of myself in Shaun when the film came out, is that too much? Yeah, too much. Never mind.

–Bob Cram

69. Buddy Pine / Syndrome (Jason Lee) | The Incredibles (2004)

Comic book super villains are a dime a dozen. Most are either bland CGI monsters that want to destroy the world by punching it to death or are glorified terrorists that have overly complicated plots that usually involve a laser shooting a giant hole in the sky. We’re living through the golden age of superhero films but as big as the budgets get and as fun as the heroes are, the villains almost always get the shaft.

The Incredibles is one of the few exceptions. Syndrome may appear on the surface to be nothing more than another byproduct of the James Bond cliche machine with his elaborate lair and impressive gadgets but it’s his motivations that set him apart from every other Bond or superhero villain. He’s not in it for world domination or a twisted sense of purpose, he’s doing it to be a hero. Every superhero he kills is just another stepping stone on his path to fame and adulation. He’s the dark side of fandom personified.

–Sailor Monsoon

68. Jesse James (Brad Pitt) | The Assassination of Jesse James by the Coward Robert Ford (2007)

Could there be anything more cinematically American than the gunslinging cowboy? A stony stare beneath a ten-gallon hat; the shimmer of iron nestled within a hunk of leather; dust kicked up beneath the thunder of hooves—images of American myth, myth that happened to at first go hand in hand with pulp novels and, shortly after, moving pictures.

Nearly a century after America’s fascination and adoration of cinema and the mythical cowboy comes a certain introspective fascination with the legend behind the myth, with the man. Enter Jesse James, perhaps the quintessential legend of the American West: a rebel embodying the American narrative up to that point, a man with a disdain for law and authority so deep and charming that he could garner the hearts and minds of his countrymen (never mind he would brandish a barrel to also garner dollars from those very countrymen). In Andrew Dominik’s The Assassination of Jesse James by the Coward Robert Ford, Brad Pitt lends his own mythical presence to show us a reality so many were willing to ignore. We see the charm of the outlaw early on. We see his folk hero status on display: robbing from the rich and, in a fashion, giving to the poor. But we are also treated with the humanity of the man, of the man who is well aware of his own celebrity. We know the isolation and depression the rebel cannot escape. The charms falter and the depression leads to the titular moment that plays perfectly well into the suicidal theory of the man’s demise. Only his end does anything but give him the peace he desired—it rekindles the legend and stokes the myth of the American outlaw as one for reverence.


67. Jamal Malik (Dev Patel) | Slumdog Millionaire (2008)

Based on the novel Q & A by Vikas Swarup (which couldn’t use Who Wants to Be a Millionaire? name for legal reasons and man, it makes all the difference in the world), Slumdog Millionaire has a unique structure in that it’s told largely through flashbacks. Jamal Malik is on the verge of winning 20 million rupees on the Indian version of Who Wants to Be a Millionaire?but there’s a problem — the producers are sure he’s cheating, they just can’t figure out how. Because there’s no way a “slumdog,” working at a minimum wage job, who has minimal schooling could possibly know these answers. The film then goes through each question, and then flashes back to an event in his childhood that supplied the answer. Some of the events are funny, some are heartwarming and others are a bit dark but they’re all memorable enough to stick with Jamal. There’s also a reoccurring subplot involving a girl he’s deeply in love with playing out within the flashbacks that informs his motivations. He needs to win to not only provide a better life for himself but for her and her family as well. Which means the viewer is doubly invested because you want him to win the grand prize and get the girl. You want him to get every victory in life because he’s just so damn likable.

–Sailor Monsoon

66. Malik El-Djebena (Tahar Rahim) | A Prophet (2009)

Depending on the country, this is either the first or film of the decade or one of the last. Either way, it’s so good, it should qualify for both versions of a top 100 films of the decade list. A Prophet is one of the best crime stories ever told. Full stop. The film is about Malik El Djebena, a young French man of Arab descent who is sent to prison after an altercation with a police officer. There, he soon finds himself under the wing of César Luciani, a veteran Corsican crime boss who recruits him to extend his grip in prison to the Muslim section. Malik’s assignments will lead him deeper into the underworld as he works his way up through the ranks. It’s two seasons worth of character drama french pressed into a single, highly efficient narrative. His journey through hell to get closer to Satan to survive the rest of the demons is as brutal as it is harrowing. It’ll stick with you.

–Sailor Monsoon

65. DJay (Terrence Howard) | Hustle and Flow (2005)

After reacquainting with an old friend and sound technician, DJ, a pimp and drug dealer who is dissatisfied with his life, suddenly decides to become a rapper. Even though he has no formal training and is much older than your typical rapper, he decides to fully commit to his newfound passion. He makes deals for equipment, sells drugs for airtime and even has his ladies secure meetings with their special talents. Since he’s used to the hustle, getting everything he needs to go legit is the easy part. The hard part is turning his raw emotions and feelings about life into a song. DJ wasn’t born a songwriter but he has lived as hard a life as the best storytellers, so it’s all about extracting those experiences and turning them into music. Watching the two sound technicians and him workshop a song, edit it, add a beat, edit it and create the lyrics for it is as engaging as a Rocky exercise montage.

Hustle and Flow has the same structure as a music biopic but is much more effective because the end isn’t built into the story. Every music biopic is about a famous musician (either alive or dead), who impacted the world in some way. If they didn’t, there’s no reason to tell the story in the first place. Since DJ is a fictitious rapper, anything could happen. He could die, become famous, crash and burn or give up. Watching his story unfold, as unpredictable as it is, is about a billion times more entertaining than they’ll ever be.

–Sailor Monsoon

64. Napoleon Dynamite (Jon Heder) | Napoleon Dynamite (2004)

In the opening scene, Napoleon clearly and definitively states that he’s going to do whatever he feels like he wants to do. He doesn’t stray from his convictions. He hides tater tots in his cargo pants, he plays tetherball by himself, and he doodles ligers. As much as Napoleon Dynamite remains an eternally wonderful character because of his quirky charm, his legacy is borne of his singular sense of affection. Napoleon doesn’t show love for his friends or brother in traditional ways, but it’s nonetheless evident. Never on better display than his incredible dance routine to Jamiroquai’s ‘Canned Heat’ on behalf of his best friend Pedro’s run for class president. I’m convinced those dance moves could solve most of the world’s ills.

–Raf Stitt

63. Władysław Szpilman (Adrien Brody) | The Pianist (2002)

Władysław Szpilman is an accomplished concert pianist with a thriving career in Warsaw, Poland in 1939. He still lives with his family, consisting of his mother and father, his brother Henryk, and his sisters Halina and Regina. He leads a happy life, surrounded by friends and family that he loves and fans that adore him. It’s as good a life as any man could ask for. But then the war happened and it would never be that way again. His entire way of life was utterly obliterated within a handful of months. Everyone he knew (and literally everyone else) was either rounded up for the death camps or was shot dead in the street. He’s all alone in a graveyard inhabited by the occasional ghoul. His tale of survival is about as punishing a watch as you could imagine. He’s trapped in that nightmare for three years. Anyone would be considered a hero for just making it to a month under those hellish conditions and he made it three years. It’s an incredible story and it’s all real.

–Sailor Monsoon

62. Amélie Poulain (Audrey Tautou) | Amélie (2001)

Amelie might take home the prize for the sweetest of the characters on this list. Her smile is infectious, and her desires remain pure. She represents the best in us. Her imagination leads her to random acts of kindness to those around her. In the end, her incorruptible desire to spread love comes back to her as we get to witness Amelie experience her own true bliss. Personally, I cannot think of a film character more deserving of a happy ending.

–Raf Stitt

61. Daniel Plainview (Daniel Day-Lewis) | There Will Be Blood (2007)

While not exactly a villain, Daniel Plainview is a pretty despicable person. He is consumed by wealth and power and openly admits to hating most people. He uses his son for manipulative purposes and has no issue with taking advantage of people’s naivety to get what he wants. But he is also impossible to take your eyes off. He is brought to life by Daniel Day-Lewis and I don’t think anyone else on the planet would have been capable of pulling the performance off. He completely embodies the role and actually frightened people on set as he stayed in character in between takes. For better or worse, the method acting paid off and helped create one of the greatest onscreen characters of the 2000s, and of all time.

–Lee McCutcheon

80-71 | 60-51

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!