The 100 Greatest 2000s Movie Characters (80-71)

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.

80. Paikea Apirana (Keisha Castle-Hughes) | Whale Rider (2002)

Tradition vs progress has been the theme of many a recent Disney movie with Brave and Moana being the best examples but Whale Rider started the trend. Kahu Paikea Apirana (Keisha Castle-Hughes), a twelve-year-old Māori girl whose ambition is to become the chief of her tribe, must fight against its antiquated traditions and customs. According to their ways, the village leader should be the first-born son, a direct patrilineal descendant of Paikea, the Whale Rider, he who rode on top of a whale from Hawaiki. Due to a family tragedy, Paikea believes it’s her destiny to fulfill that position and she’s going to fight tooth and nail to get it. If this was an American film, that plot synopsis would 100% suggest a grrl power message with an uplifting ending and a soundtrack that’s indistinguishable from a Kidz Bop collection.

But this isn’t an American film. It’s more concerned with reality than a feel good storyline. Whether she becomes the chief or not, isn’t the point of the film. Nor is it about a young girl singlehandedly changing the status quo. It’s about challenging norms and traditions. Just because this is how it’s always been done isn’t enough justification to not try an alternative. As long as the situation doesn’t become worse, there’s nothing inherently wrong with change. The world needs new perspectives from time to time. Paikea isn’t trying to dismantle any systems but to just work within them. She doesn’t want the job to prove any point or to make anyone else look bad. She just feels an obligation to the position and hates the fact that she has to fight for it in the same place because if she was born a male, it would be given to her. That’s the major difference between this and those Disney movies. In Brave and Moana, the main characters are fighting for their freedom, in Whale Rider, she’s fighting for equality.

–Sailor Monsoon

79. Caden Cotard (Philip Seymour Hoffman) | Synecdoche, New York (2008)

When it comes to the work of Charlie Kaufman, you either think he’s a genius or one of the most pretentious writers working today. There’s almost no in between with Synecdoche, New York being the perfect litmus test. Roger Ebert named it the best film of the decade, while Rex Reed, Richard Brody, and Roger Friedman all labeled it one of the worst films of 2008. Where you’ll fall depends on the level of enjoyment you get from dissecting motifs, unraveling symbolism, your knowledge of Jungian psychology and postmodernist philosopher Jean Baudrillard’s concept of simulacra and simulation, your threshold for surrealism and your love for Philip Seymour Hoffman.

That check list alone is about as hipster douchebag pretentious as you can get, so I get it if you just checked out completely but if you managed to make it to the end without your eyes rolling so hard that they popped out of your skull, you most likely subconsciously nodded in appreciation of Philip Seymour Hoffman. There’s not a single cinephile walking the Earth that didn’t love him when he was here and doesn’t miss him now that he’s gone. He was one of the greats and this is one of, if not, the best performance he ever gave.

Even the critics who hated this movie sung the praises of Hoffman because even a blind man could see how much he has to do in this movie. If Shrek’s analogy of ogres being like onions is correct, than Caden Cotard is the king of the ogres because he’s nothing but layers. He’s an ailing theater director who’s work on an increasingly elaborate stage production about his life begins to blur the boundaries between fiction and reality. His family is falling apart, his body is falling apart, the production he’s working on is falling apart and his mind is slowly deteriorating. That’s plenty of material for any actor to really sink their teeth into but since this is a Kaufman film, that’s far from the only things going on with Hoffman’s character. There’s enough evidence to support any number of theories including the fact that he might be dead the entire time, a hypochondriac, a man suffering from Cotard’s syndrome, a woman, a homosexual or just another actor hired to play Caden Cotard. There’s more going on with this character than just about any other in film history.

–Sailor Monsoon

78. Albus Dumbledore (Richard Harris & Michael Gambon) | Harry Potter film series (2001–2011)

The headmaster of Hogwarts and founder of the Order of the Phoenix, Albus Dumbledore is an important character in J.K. Rowling’s Wizarding World franchise. The character fulfills a similar role to Yoda in the Star Wars films, training and guiding his young protege (in this case Harry Potter instead of Luke Skywalker) to defeat the villainous threat looming over the story. Richard Harris originally portrayed the wise, old wizard in the first two Harry Potter films, showing off Dumbledore’s more mischievous and light-hearted side. It is well known that Harris only took on the role of Dumbledore at the request of his grandchildren, who told the acclaimed actor that they would never speak to him again if he refused the offer to play the character. After Harris’ passing in 2002, Michael Gambon stepped into the role and portrayed the character more mysteriously and darker than Harris had. And while the Harry Potter films featured a large number of popular British actors inhabiting the teaching staff at Hogwarts, it’s hard to that anyone could have done a better job at playing Dumbledore than the two thespians who successfully brought the character to life.

–Marmaduke Karlston

77. Wikus van de Merwe (Sharlto Copley) | District 9 (2009)

After his Halo film fell apart, Neill Blomkamp went back to the project that got him hired in the first place — Alive in Joburg. It was a six minute short about aliens trying to integrate into a neighborhood in Johannesburg. It was more of a tech demo than an actual narrative short but there was clearly enough meat on the bone to be expanded into a feature length film. He kept the faux documentary style, fleshed out the world and the aliens and even ladled on some political subtext for good measure. He had all the right ingredients to make a great cake but what brought it all together, the frosting if you will, was the decision to cast Sharlto Copley as the lead. He was a friend of Blomkamp’s who helped produce the original short but who had almost no acting experience.

Whoever fronted the money almost definitely pushed for a bigger name but Blomkamp stuck to his guns and it’s the best decision he’s ever made in his career. Every time he feels down about all the various projects he’s been attached to falling apart, he should take solace in the fact that he gifted us Sharlto Copley. It’s one of those once in a decade discoveries like Nick Frost, Michael Clarke Duncan or Rosario Dawson that comes out of nowhere and instantly becomes one of your favorite screen presences. His performance as Wikus Van De Merwe wasn’t just a great debut, it’s one of the best characters of the decade (hence it’s inclusion.) His arc from being a goofy, by the book MNU agent to being hunted as an alien hybrid is as entertaining as it is heart breaking. He sells the unintentional comedy just as well as the tragedy. He’s losing himself and he’s desperate. It’s a lot for any actor to convey and for a first timer, it’s insane as a debut. His performance is one of the reasons the film was a monster success and it could be argued was what bought Blomkamp his next three movies. If only he could write something for his buddy that was as good again.

–Sailor Monsoon

76. Walter Kovacs / Rorschach (Jackie Earle Haley) | Watchmen (2009)

When I think of the Watchmen film, I think of Rorschach. I think of his twisted face as he utters the infamous line ‘I’m not locked in here with you. You’re locked in here with *ME*’. Even though the line is taken straight from the comic, a large part of what makes it memorable is how Jake Earle Haley spits the words out with complete venom. He also looks the part, from his size and shape, to his hair and facial expressions. He doesn’t have the biggest part in the movie, but he is one of the most memorable things in it. Yes, there were a few substantial changes made to his character. He’s essentially a less extreme, toned-down version of Rorschach. He feels a little more badass and less creepy than the comic book iteration. But he is still one of the best comic book characters, and characters in general, from the 2000s.

–Lee McCutcheon

75. Jack Byrnes (Robert De Niro) | Meet the Parents (2000)

We deserve more funny Robert De Niro roles. Kudos to director Jay Roach and co-star Ben Stiller for uncovering De Niro’s hilarious side. Not all dramatic actors can translate to the world of comedic acting. De Niro perfectly captures the absurdly terrifying experience of meeting your in-laws and everything that can go wrong while doing so. As Jack, De Niro maintains the gravitas which makes him one of the greatest actors of all time, while simultaneously being able to get loose in a way that allows the comedy to flow. Jack is the ultimate hard shell to crack. Watching Stiller’s Greg Focker attempt to continuously fail to crack the shell and Jack’s unfaltering resistance to it remains one of the best comedic rivalries in any movie.

–Raf Stitt

74. Claireece “Precious” Jones (Gabourey Sidibe) | Precious: Based on the Novel ‘Push’ by Sapphire (2009)

One of the great fuck ups in Oscar history is giving Sandra Bullock the award for The Blind Side over Gabourey Sidibe for Precious. It’s an egregious example of rewarding the actor and not the performance. It’s the same reason Julia Roberts won for Erin Brockovich, Al Pacino won for Scent of a Woman or Denzel Washington winning for Training Day. The Academy either felt like it was their time or were rectifying a fuck up. Since this was Bullock’s first nomination, it was most definitely the former. Or maybe I’m giving them too much credit. It could very well be just as simple as they just didn’t see it. The majority of the Academy is made up of crusty ass old white dudes and Precious might’ve been too much for them. It’s not an easy film to watch and Sidibe’s performance is as raw as it gets.

If it wasn’t for Mariah Carey, the director could’ve easily passed certain parts of this off as a documentary. That’s how real every actor feels in this movie. There’s not a shred of artifice anywhere in Precious. It’s documenting a hard reality for many people and it never wants sugar coats the uglier aspects of the story. Precious goes through a lot. She does not have an easy life. Her mother is a monster, her living situation is trash, her neighborhood is awful and her future prospects are non existent. Every day is a struggle and that’s putting it mildly. But as bad as it is, it never turns into Harmony Korine or Gaspar Noé film. Sidibe keeps it from becoming unbearable. Her indomitable spirit balances out the depressing elements. She won’t be beaten by life. Even though her life is terrible and it might never get better, she perseveres. Precious is one of the strongest characters of the decade and she was fucking robbed at the Oscars.

–Sailor Monsoon

73. Ennis Del Mar (Heath Ledger) and Jack Twist (Jake Gyllenhaal) | Brokeback Mountain (2005)

Two men intertwined by an undeniable fate – Ennis Del Mar and Jack Twist share a love that is forbidden and raw. We can’t help but cheer for them even though we know they are unlikely to ultimately end up together. As much as anything else, Brokeback Mountain is a movie about clashing forces. Our central clashing forces are Ennis and Jack. They are the yin to each other’s yang – polar opposites that cannot exist without the other. Their tragic love story is also filled with an unmatched beauty. They can’t quit each other, and we can’t quit enjoying them as incredible film characters.

–Raf Stitt

72. Sergeant First Class William James (Jeremy Renner) | The Hurt Locker (2008)

Although he had been working for well over a decade by this point, The Hurt Locker was Jeremy Renner’s breakout role. It buys him the rest of his career. He gets The Town because of it (along with another Oscar nom) and that eventually leads to Hawkeye. He might’ve gotten the shit ever of the stick when it comes to Marvel superheroes but he made the character his own. But as good as he is, there’s a part of me that wishes he passed on the role because his career hasn’t been as interesting as it was before Thor and The Avengers. Basically what I’m saying is, he needs to make more of this and less of The Bourne Legacy. The longer he gets away from this, the harder it’ll be for audiences to even remember a time when he was amazing. Because holy shit is he amazing in this. He plays bomb diffuser Sergeant William James who is assigned to dispose of explosive devices in Iraq. It’s a task that is incredibly dangerous, but James has grown obsessed with placing himself in life-threatening scenarios, and has trouble adjusting to a normal life. His addiction to near death experiences is a by product of his post-traumatic stress disorder. It’s an interesting and extremely complicated depiction of a war hero. He’s undoubtedly saving lives by putting his life in danger but he’s only putting his life in danger for the adrenaline rush. It’s the kind of complexity I wish Marvel superheroes had but oh well.

–Sailor Monsoon

71. Penny Lane (Kate Hudson) | Almost Famous (2000)

More than anything else, Penny Lane’s engine is run by music. Her motivation is as pure as any other character in Almost Famous. And although she isn’t the protagonist of the film, it would be hard to argue against her being the heart and spirit of the movie. Watching her run through the airport to the tune of Led Zeppelin’s “Tangerine” is one of the best needle-drops in movie history. I cry every single time. Kate Hudson’s charm shines through in an infectious manner. Penny Lane’s care for who and what she loves rubs off on us by the end of the movie, which is what a great movie character should do.

–Raf Stitt

90-81 | 70-61

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!