11. Dignan (Owen Wilson) in Bottle Rocket (1996)

We should all strive for the long-term optimism that Dignan (Owen Wilson), the protagonist of Anderson’s first feature film Bottle Rocket, has in his life’s blueprint. However, we probably shouldn’t base a 75-year plan on stumbling up the underworld ladder of criminality. Still, Dignan’s absurdist exaggeration of relatable human emotions—like the fear of mediocrity and the yearning for purpose—became an Anderson trademark that has endeared his characters to us for decades.

While Dignan isn’t as fleshed out as Anderson’s later characters, the depth of his delusion shifts from comedic to cautionary in the film’s final moments. As he sits in prison, his last words—“They’ll never catch me, man. ‘Cause I’m fucking innocent.”—perfectly encapsulate his unwavering belief in his own fantasy. Even in comedy, Anderson creates characters who can tickle our funny bone while simultaneously breaking our hearts.