In honor of the second season premiere of "The Blacklist", where James Spader plays good guy/bad guy Raymond “Red” Reddington, we took a look back at Spader’s storied history of playing not-so-nice guys. While the '80s saw him showcase his evil yuppie side, he graduated to intense, morally ambiguous guys in the '90s, but his latest role might have him on his worst behavior yet.
'Pretty in Pink' (1986)
Probably the first step on Spader’s path to pop cultury villainy was the snobby Steff in “Pretty in Pink.” While “The Blacklist”’s Red engages in global espionage, Steff partakes of a slightly more mundane form of bad guy tactics: He’s a jerk to Molly Ringwald’s Andie because she comes from a poor family, and tries to discourage rich kid Blane from going out with her. The nerve!
‘Less Than Zero’ (1987)
After “Pretty in Pink,” there was no going back to good. When the first of the Brett Easton Ellis movies — about Los Angeles’ young, pretty and sometimes drugged-out — needed a scary dealer, they turned to Spader, who slicked back his hair to terrorize his former “Tuff Turf” costar, Robert Downey Jr. Spader wouldn’t have many nice roles until “Sex, Lies and Videotape,” and even there he’s playing a guy cursed with impotence.
By 1994 Spader was freely wobbling back and forth between good and evil. He was firmly on the latter side in Mike Nichols’ curiously polished trashy werewolf movie, where he’s the guy who makes the mistake of sleeping with Jack Nicholson’s wife — right before Nicholson turns lycanthrope. Spader even gets his shoes micturated upon by Jack.
‘2 Days in the Valley’ (1996)
The immediate post-“Pulp Fiction” era was a nasty one, with weak imitations flooding the market. One of those was this Altmanesque ensemble piece, which counted among its many characters Spader’s bespectacled, psychopathic hitman. He wields a permanent smirk as he guns down chunks of the cast or plays with his girlfriend (Charlize Theron).
'The Office' (2011-2012)
So maybe Robert California wasn’t quite as bad as some of Spader’s other nefarious roles, but he wasn’t exactly a good guy, was he? He seemed to thrive on keeping all of his employees slightly off-balance with his intense but unreadable management technique, and we all know there’s nothing worse than a bad boss.
'The Avengers: Age of Ultron' (2015)
In perhaps his strongest run of villainy yet, Spader will be voicing Ultron, the villain in the upcoming “Avengers” sequel. Sure, some of those other guys wreaked havoc in their high schools, or across the country, but Ultron? That guy’s working some interstellar wickedness.