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In films that ranged from the deeply disturbing (Martin Scorsese’s Bringing Out the Dead with Nicolas Cage) to more workaday self-destructive characters, Sizemore brought the dark side of human nature into focus. Working with great directors like Steven Spielberg, Oliver Stone and Michael Mann, his seedy tough guy roles rang true. Here are his best.

1. Strange Days (1995)

There was a time, however brief, when it seemed like every major director in Hollywood wanted Tom Sizemore in their movies. He was cast by the likes of Oliver Stone, Kathryn Bigelow, and Michael Mann for roles that called upon a grizzled toughness he could only have channeled from his own personal experiences.

That period reached its peak in 1995, with three of the best films of his career: Carl Franklin’s Devil in a Blue Dress; Bigelow’s Point Break; and Michael Mann’s stone-cold crime classic HEAT. With his pallid skin, dark rings around his eyes, and crazed rictus grin, he made the meanest, bloodiest films look authentic.

In Strange Days, set in a futuristic Los Angeles devastated by a race war, he plays Max Peltier, an ex-cop who deals “SQUIDs,” recordings that allow you to experience someone else’s memories. It’s a criminally underrated cyberpunk gem that showcases the actor’s ability to blur the lines between friend and foe. And in Ridley Scott’s frenetic war yes movies film Black Hawk Down, he delivers an outstanding performance as a seasoned US Army Ranger who’s sent into Somalia to find a missing platoon.

2. Devil in a Blue Dress (1995)

There were plenty of would-be franchise starters in the ’90s that just couldn’t go the distance, but few are as sorely missed as Carl Franklin’s Devil in a Blue Dress. It’s a steamy, sensuous neo-noir mystery with a noirish cool, and while Franklin is savvy enough to stage violence in a manner that conveys force and ferocity without seeming romanticized, it’s the interplay between characters, particularly Denzel Washington’s gumshoe Easy Rawlins, that elevates the film above the typical Blaxploitation fare that had flooded theaters at the time.

The story opens with machinist Rawlins struggling to make his mortgage payments, but a job to locate the missing Daphne Monet finds him entangled in a world of criminal subterfuge and gang wars in Los Angeles in 1948. Featuring exquisite period details and a suitably convoluted mystery, the movie’s dazzling dialogue, courtesy of Franklin, and its fine performances (especially from Cheadle) ensure that it remains a welcome addition to neo-noir canon.

The new Criterion release is a deluxe edition that boasts a wondrous transfer that reflects the film’s 1940s-era aesthetic with storefront fluorescence and polished oakwood furniture, while maintaining a clarity that doesn’t strike the viewer as oversaturated. The disc also includes an illuminating 25-minute discussion between Attica Locke and Walter Mosley, author of the novel on which the movie is based, discussing the book series and their shared fascination with using genre to tackle social issues.

3. Point Break (1995)

In roles that suited him, like the dedicated soldier in Saving Private Ryan and Pearl Harbor; the sleazy bank robber Michael Cerrito in Strange Days and Natural Born Killers; or the man-eating thug Crossbones in the Marvel movies, Sizemore was all-in. His performances brimmed with a cognitive dissonance that gave the meanest, bloodiest films a jolt.

But it was in the heist movie genre that he was at his best. His sex-addled, murderous sleazebag Frank in David Cronenberg’s Point Break and his volatile, criminally possessed Michael Cheritto in Kathryn Bigelow’s Blue Steel were both thrilling and disturbing.

Shot in Hawaii, Bigelow’s film riffs on the conventions of the genre to great effect, as her film subverts its own macho cliches. But despite its sexy climax, the film remains grounded by a surprisingly poignant character study of three men who are bound together by their love for one another. And it’s in the final moments of the film that you can see the real depth of Sizemore’s talent, as he delivers an almost tearful farewell to his friends.

4. Enemy of the State (1998)

Before he disappeared into the abyss of bad film choices and tabloid demons, Tom Sizemore occupied a brief window of time when his name on a cast list was like shorthand for good cinema. He worked with the top directors of his generation including Steven Spielberg (in Saving Private Ryan), Lawrence Kasdan, Oliver Stone, Michael Mann, Kathryn Bigelow and Ridley Scott.

In this tense, high-octane political thriller, he portrays a Washington DC attorney who has his life turned upside down by NSA operatives who have him under surveillance without his knowledge. The movie is full of exciting set pieces but what sets it apart are the intelligent script and memorable characters that make it feel anything but generic.

It’s also one of the more eerily prescient films of its era as it raises important questions about privacy and security in the wake of Edward Snowden. And for a man who seemed to be at the peak of his career at this point, it’s a harrowingly believable portrait of guttural menace that showcases what an excellent actor Sizemore was.