30. Drexl – “True Romance” (1993)
Not one to let a wig and makeup do all the work, Gary Oldman focused all the lunges and jitters of his hyper-physical period into this trigger-happy dirtbag. The irony of seeing such a gross character blatantly appropriate aspects of black culture isn’t lost on us in light of one of the most prominent criticisms levied at his creator.
29. Clifford Worley – “True Romance” (1993)
In a fast-paced film wearing an oversized heart on its sleeve, Clarence Worley’s father Clifford brings a bit of genuine pathos. Tarantino may not have cast or directed “True Romance,” but Dennis Hopper seems like the choice he would have made, and Hopper’s gruff and honest paternal figure is surprising and welcome, even when he gets nasty provoking the gangster played by Christopher Walken.
28. Aldo Raine – “Inglourious Basterds” (2009)
We’ve seen weirder things than an Alabama hillbilly leading an all-Jewish squad of Nazi killers, but Brad Pitt’s exaggerated accent pushes this Army officer fully into a cartoonish realm. Raine’s anti-facist exuberance is infectious, but he really gets interesting when, dismally under-prepared, he infiltrates the very core of the political force he hates.
27. Vincenzo Coccotti – “True Romance” (1993)
In one sequence, thanks in no small part to a pitch-perfect performance from Christopher Walken, this mobster is enshrined as one of the unforgettable silver screen gangsters. Who else could deliver “You’re a cantaloupe!” with such panache? Coccotti is showy with articulation of his own dangerous nature, but Blue Lou Boyle’s consul doesn’t hesitate to back up his talk.
26. Ordell Robbie – “Jackie Brown” (1997)
He’s ambitious and determined, but this small-time gun runner isn’t nearly as smart as he thinks he is. Samuel L. Jackson nails Robbie’s demeanor, keeping us hooked with snappy patter while revealing just enough vulnerability to make his failures even more satisfying than his brief moments of success.
25. O-Ren Ishii – “Kill Bill: Volume One” (2003)
This top Tokyo crime lord climbed to her gangland leadership position over a hill of bodies, but the commanding and ruthless assassin is not without some lingering glimmers of compassion for her old compatriot. Implications of serious friendship between O-Ren and Beatrix Kiddo add depth to the first heavy antagonist in “Kill Bill,” and O-Ren’s elegant end is as respectful as the violent story gets.
24. Mr. Blonde – “Reservoir Dogs” (1992)
We’re told about more of Blonde’s out of control violence than we actually see, but even before White and Pink are cowed and angered by his diamond heist shooting spree, we’ve seen Michael Madsen use an empty stare and charming smile to create a deeply disconnected sociopath. He’s among the most authentic villains in Tarantino’s films, and possibly the most frightening.
23. Butch – “Pulp Fiction” (1994)
This Bruce Willis character riffs on an old film noir trope: the fighter who has a plan to rip off domineering bookmakers. Yet Tarantino pushes him into weird territory, making what felt like a very familiar character part of the film’s most bizarre turn. Events in the sadist’s basement also gives Butch a chance to show his true character, when he turns back to save Marcellus Wallace from a miserable fate.
22. Zoe Bell – “Death Proof” (2007)
It might seem a bit odd to call the stuntwoman’s first star turn a “character,” as the “Death Proof” daredevil seems to be basically a play on her real-life persona (even credited as ‘herself’). That said, it would also be criminal to overlook Bell’s incredible physical performance as the core of the exploitation homage’s electric nervous system.
21. Elle Driver – “Kill Bill” (2003-4)
Like an inverted image of O-Ren Ishii’s steely killer, Daryl Hannah’s spiteful, bitter hitwoman is the most devious and grimy nemesis Beatrix must face. Appropriately, their brutal battle is a wince-inducing highlight, and Hannah spits venom (“that’s right, I killed your master!”) as if inspired by the very sort of creature that presumably ends her life.