The 100 Greatest 2000s Movie Characters (100-91)

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.

100. Wilson | Cast Away (2000)

I’m about to sing the praises of a volleyball, so bear with me. Cast Away is a two-and-a-half-hour showcase for Tom Hanks’s acting ability. For the majority of the movie, Hanks is the only actor, taking us along on Chuck Noland’s journey to survive. But he’s not necessarily alone. His co-star is Wilson, a volleyball stranded on the island with Chuck. With a smiling face in a bloody palm print, Wilson becomes Chuck’s only companion and over time, his friend and confidante. He becomes fully human to Chuck, and to the audience. We care about this volleyball because Chuck cares about this volleyball. When Chuck decides to risk everything and try to get back home, there’s no way he would leave Wilson behind. And when Wilson falls off the raft and begins to float away, we feel Chuck’s desperation as he tries to save not a mere volleyball, but his only friend of the past four years. When he fails, he grieves the loss of Wilson, and so do we.

–Romona Comet

99. Han Lue (Sung Kang) | The Fast and the Furious: Tokyo Drift (2006)

Often considered the black sheep of The Fast Saga, the third entry in the popular street racing/action film franchise was, at one point, a standalone film about an American teenager (who looked 30) named Sean, who upon arriving in Tokyo to live with his father, has to learn how to drift cars so that he can get the girl and defeat his rival, the Drift King. The film would be mostly forgotten about today if not for one character: Sung Kang’s Han Lue. Kang’s performance as Han was so damn memorable that director Justin Lin had no choice but to bring the fan favorite character back for a quick cameo in 2009’s Fast & Furious. With each new sequel Han was brought back for, Tokyo Drift was retroactively pushed further down the Fast timeline until 2015’s Furious 7 had no choice but to catch up to the events of Tokyo Drift (in glorious fashion, suddenly making Han’s random death in the 2006 film have a whole new meaning). For a character that was initially supposed to be a cool, rich, and Miyagi-type mentor to Sean, Han’s long-lasting popularity allowed for the franchise to diver deeper into the character’s past to show fans the events that led to the Han seen in Tokyo Drift. He’s also the only character in the franchise to have been brought back from the dead twice, so yeah, Han’s the best. No contest.

–Marmaduke Karlston

98. Lieutenant Aldo Raine (Brad Pitt) | Inglorious Basterds (2009)

Overshadowed somewhat by the revelation that was Christoph Waltz in his career-making turn as Hans Landa, Inglorious Basterds boasts another noteworthy performance in the form of Brad Pitt’s Lieutenant Aldo Raine. Pitt, in his first collaboration with director Quentin Tarantino, established an instantly iconic character. Jaw jutting out, sporting a ‘tache, and talking about “killin’ gnatsies” in an unforgettable Southern drawl, the leader of the Basterds cuts an impressive figure onscreen.

–D.N. Williams

97. Rob Gordon (John Cusack) | High Fidelity (2000)

The first time I saw High Fidelity, I didn’t like it. I mean, the movie itself was fine. I thought Jack Black was having fun and the fourth wall breaks were actually implemented well. I just couldn’t stand the main character. I thought he was at best an annoying whiner who couldn’t move on and at worst, an obsessive stalker and shitty boyfriend. He belongs in that weird area between an incel who feels entitled and “the nice guy” who bitches after he gets it but then loses it. He never self-reflects and wonders whether or not he’s the common denominator. He’s the absolute worst and every time he’s on screen, my teeth are in danger of getting ground into dust from me cringing so hard. The fact that he then became a cult hero amongst similar nerds was even worse. Until I realized years later that he was supposed to be garbage, that was the point. The film, much like Fight Club, is embraced by the type of people the film is actively mocking. High Fidelity is not an endorsement of this type of character, it’s a condemnation. You are not supposed to relate to Rob Gordon or find him likable. You’re supposed to recognize his toxicity and use it as a guide book on what not to do or what to avoid. He’s one of the most unlikable humans committed to celluloid and now that I know it’s intentional, I consider him one of the best.

–Sailor Monsoon

96. Bob Harris (Bill Murray) | Lost in Translation (2003)

Sofia Coppola once said that she wanted Bill Murray to star in Lost in Translation so bad, that she not only offered him the role outright, she wouldn’t have made the movie if he had turned it down. In her eyes, there was only one Bob and that was Murray and since Bob is the engine that drives the film, without the perfect Bob, making it would be pointless. She needed a lovable sad sack that could convincingly have an affair, albeit it an emotional one, with a much younger and much prettier woman.

And while the character is a former action star — a thing Murray is most definitely not — he works better in the role than say a Bruce Willis or a Liam Neeson because he’s a clown and clowns mask pain better than anyone else. Bob is a man well past his mid life crisis and is now moving into late stage depression. The point when you have to accept the fact that your glory days are over and if you didn’t leave a legacy behind, it’s far too late to do so now. He’s in Japan not to shoot a new movie or even a small part in a famous TV show, but to do some whisky commercials. It’s the last gasp at relevancy for every fading star and he knows it. He’s horribly depressed and although he has a family back home, deeply alone. He spends his nights drinking by himself at mostly empty hotel bars until one night when he uses the last of his charm to talk to an American student Charlotte (Scarlett Johansson) who’s going through her own bit of depression and they immediately hit it off.

The film then plays as a love story between two people who were never destined to be together but needed each other at that one moment. It’s a fleeting affair that ended almost as quickly as it began but will live with them forever. It’s the type of love story Woody Allen loves to make but works infinitely better here because Bill Murray never comes off as a creep or horn dog. At a certain point, you no longer see their ages and just recognize them as two lonely souls who were lucky enough to be caught in each other’s orbits. Lost in Translation couldn’t have worked without Murray. No other actor could make you want to immediately go on an adventure with them, fall in love in the process and leave you without breaking your heart. Coppola was right, he is Bob.

–Sailor Monsoon

95. John Kramer / Jigsaw (Tobin Bell) | Saw series (2004-17)

To summarize a backstory that gets increasingly more and more convoluted as the series progresses: After being diagnosed with an inoperable tumor, John Kramer (Tobin Bell) decides to take his own life. Miraculously, the suicide attempt fails but instead of counting his blessings or hitting the titty bar, Kramer decides to dedicate his life to punishing those who take their life for granted.

From that point forward, he becomes Jigsaw: torture game enthusiast with a penchant for puppets and pig masks. If you ask hundred horror enthusiasts why they like horror, I’d bet over half of them would say the gore effects. There’s nothing better than seeing creative kills done practically and the Saw series have some of the most ingenious kills in all of horror. And that’s far more important than whatever bullshit backstory they use to pad the length of these films.

–Sailor Monsoon

94. Derek Zoolander (Ben Stiller) | Zoolander (2001)

A true testament to the comedic skills of Ben Stiller, he took what easily could’ve been a one-note Saturday Night Live character and made him into an instant icon. Zoolander is a male model who’s dumb. That’s all there is to him. That’s his entire character. He’s the walking personification of “pretty but dumb”. His idiocy is the punchline of every joke. And yet, somehow it still works. Even the gag that every one of his looks is identical has a great payoff. I think a large part of his effectiveness is having him bounce between characters who are bemused and/or frustrated with his lack of intelligence, characters that are just as dumb as he is and situations that are outright bizarre. It helps keep the joke fresh, otherwise, it would’ve turned stale and repetitive like the sequel. Stiller was all over this decade but he never produced anything half as funny as Derek Zoolander.

–Sailor Monsoon

93. Davy Jones (Bill Nighy) | Pirates of the Caribbean: Dead Man’s Chest (2006)

The Pirates of the Caribbean franchise has a knack for fun-to-watch bad guys. It was hard to imagine a more entertaining foe than The Curse of the Black Pearl’s Captain Barbossa, but when Davy Jones clicks and slurps his way into Dead Man’s Chest, it is a sight to behold. Jones is the captain of the Flying Dutchman who was once a mortal pirate. He fell in love with the sea goddess Calypso and was entrusted with the task of ferrying the souls of those lost at sea to whatever comes next. After some lovers’ drama, Jones convinces the other sea captains to bind Calypso in human form, then cuts out his own heart and stores it in a chest (okay so maybe he’s a little overdramatic). He proceeds to pervert the purpose of his ship, damning himself to become the tentacle-faced captain we meet in the second installment of the Pirates franchise, along with his damned crew, who all look like they’ve spent too much time around Dr. Moreau’s island. Jones is a fascinating villain, and while most of what we see of Jones is CGI, Bill Nighy does a tremendous job of imbuing him with life using only his devilishly distinctive voice and expressive eyes.

–R.J. Mathews

92. Leonidas (Gerard Butler) | 300 (2006)

Zack Snyder’s movie adaptation of Frank Miller’s graphic novel is made mostly of machismo, oiled muscles, and slow motion. It’s a film that could easily become nothing but bloody spectacle (and I’m sure for many that is EXACTLY what it is), but for me, that film is saved by Gerard Butler’s turn as Leonidas, King of the Spartans. While the character is indeed as full of machismo, oiled muscles (and slow motion) as the film, Butler imparts a dark and sardonic wit to the character that saves him from being a simple stereotype. He’s almost the ancient world equivalent of an 80’s action hero, tossing off one-liners and spearing bad guys with equal energy. The movie is full of great action moments and macho one-liners, but nothing beats the moment when he lets the Persian messenger know what he thinks of bending the knee. It’s been parodied and memed to death, but “this is SPARTA!” is still one of the great badass moments in cinema.

–Bob Cram

91. Edward Cullen (Robert Pattinson) | Twilight (2008)

For about seven years in the late 00s, the world was gripped in Twilight fever. You couldn’t go anywhere without seeing Team Edward or Team Jacob shirts. Couldn’t turn on the television without seeing a commercial or hearing a news story about it. Couldn’t go online without seeing gifs or memes or videos about how much it sucks. A poorly written YA soap opera turned poorly written AND directed softcore porn for tweens became a monster cultural sensation. A large part of that was due to Robert Pattinson as Edward. Teen boys (and most but not all teen girls) didn’t really give a shit about Bella and anyone that’s Team Jacob is a liar, so it stands to reason that Edward was the draw. He had as many devotees as detractors. One side loved his obsessiveness, brooding and dreamy eyes, while the other side thought he was a lame-ass sparkle fairy. But either way, you had an opinion. And most likely, a strong opinion. This is more than one can say about any character from Divergent or Hunger Games or Maze Runner or Fifty Shades. Edward was a conversation starter. You either loved him or hated him. Either way, you talked about him or were forced to listen about him multiple times for about five years. That’s a helluva run for a sparkle fairy.

–Sailor Monsoon

Last Decade | 90-81

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!