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‘Blacklist’ Star James Spader Then & Now: How He Became The Guy We Love to Hate

From a preppy jerk in 'Pretty in Pink' to a smooth-talking layer on 'Boston Legal' he's a good bad guy

In July 2023, the popular NBC thriller series The Blacklist aired its final episode after an impressive 10-year run that yielded 218 episodes. Played by Emmy Award-winning actor James Spader, the protagonist Raymond “Red” Reddington is a mysterious former government agent turned criminal who works with the FBI to track down a “blacklist” of dangerous individuals that he has a unique level of access to.

Seeing as Spader has played a variety of strange, morally ambiguous characters in his 40-plus year career, Reddington was an ideal role for the award-winning actor. Now that Spader has hung up Reddington’s fedora for good, we’re taking a look back at some of James Spader young roles in iconic movies of the ’80s and ’90s.

James Spader in The Blacklist (2013)
James Spader in The Blacklist (2013)Davis/Universal Tv/Sony Tv/Kobal/Shutterstock

James Spader young

Spader’s first role was a bit part in the 1978 movie Team Mates, when he was just 18 years old. While he was struggling to make it as an actor, he worked odd jobs which included shoveling horse manure at a stable and teaching yoga.

In 1981, he had a small role in Endless Love, which starred teen queen Brooke Shields. From there, he took on parts in a number of early-’80s TV movies, and in 1985, he had his first starring role in Tuff Turf, where he played a teen who becomes entangled with a gang. The movie also featured Kim Richards, who is best-known today for being one of the Real Housewives of Beverly Hills, and a young Robert Downey Jr.

Related: Young Robert Downey Jr.: A Look at His Dramatic Hollywood Journey From Bad Boy to Three-Time Oscar Nominee

James Spader, Kim Richards, Robert Downey Jr. in Tuff Turf (1985)
Tuff Turf (1985)New World Pictures/Kobal/Shutterstock

Spader soon became a fixture of the teen movies of the time, which were led by the so-called “Brat Pack” of Emilio Estevez, Anthony Michael Hall, Rob Lowe, Andrew McCarthy, Demi Moore, Judd Nelson, Molly Ringwald and Ally Sheedy.

Rob Lowe and James Spader in Bad Influence (1990)
Spader, right, with Brat Pack star Rob Lowe in Bad Influence (1990)Epic/Kobal/Shutterstock

While Spader, with his luxuriant blond hair and intense stare, had Brat Pack looks, he was a bit more — shall we say — quirky than other members of the group, and frequently played unsavory yet compelling types — a trend that would continue throughout his career.

As he described it in a 2014 Rolling Stone profile, “I didn’t really look like a character actor, yet those were the roles I loved to play… If you were a character actor who didn’t necessarily look like a character actor, you had to play bad guys.”

Related: Matt Dillon Young: A Look Back at the Handsome Actor’s Days as the Ultimate ’80s Teen Idol

One of his most memorable roles in this vein was in the classic 1986 John Hughes movie Pretty in Pink, where he played Steff, an obnoxious, preppy guy who was constantly smoking and sneering while wearing Miami Vice-style linen suits. As legend has it, Spader played a jerk so convincingly that the film’s casting director had to overcome a visceral distaste for the actor in order to give him the part.

James Spader in Pretty in Pink (1986)
Spader in Pretty in Pink (1986)Paramount/Kobal/Shutterstock

More oh-so-’80s roles followed, including turns in Mannequin (as a sleazy store manager), Baby Boom (as a sleazy businessman), Less Than Zero (as a sleazy drug dealer) and Wall Street (as a sleazy lawyer). Less Than Zero, a stylish 1987 adaptation of the popular novel, saw Spader and Robert Downey Jr. pair up once again.

Robert Downey Jr. and James Spader in Less Than Zero (1987)
Robert Downey Jr. and James Spader, right, in Less Than Zero (1987)20th Century Fox/Kobal/Shutterstock

Spader won acclaim two years later for his starring role as a man who videotapes women talking about their sex lives in the indie movie Sex, Lies, and Videotape. The movie was shot for a low budget but went on to be a success (thanks in part to its provocative subject matter) and helped spawn a new generation of artsy independent filmmaking. In a contemporary review, film critic Roger Ebert compared Spader to a young Marlon Brando and James Dean. Following this part, Spader repeatedly took roles in sexually-charged dramas, among them White Palace, Dream Lover, Crash and Secretary.

James Spade in Sex, Lies, and Videotape (1989)
Sex, Lies, and Videotape (1989)Moviestore/Shutterstock

While he’s best known as the guy you love to hate, Spader’s filmography in the ’90s and ’00s showed his capacity for taking on a wider range of roles in different genres. He starred in comedies (Critical Care), sci-fi movies (Stargate) and even historical biopics (he played Republican Party operative William N. Bilbo in Steven Spielberg’s Lincoln). While Spader may have told Rolling Stone “It can never, ever, ever get weird enough for me,” some of his roles are certainly weirder than others.

James Spader in White Palace (1990)
Spader in White Palace (1990)Moviestore/Shutterstock

James Spader TV roles

Before The Blacklist, Spader played Alan Shore in the legal drama The Practice from 2003 to 2004. He won an Emmy for the role, and then reprised it in a spinoff, Boston Legal, alongside William Shatner and Candice Bergen.

In a rare feat, he’d win another Emmy for the same role for his work in Boston Legal, and the popular series ran for five seasons, from 2004 to 2008. Spader and Shatner became friends, which came through onscreen, and Shatner described Spader as an actor with a “penchant for detail and the truth.”

Mark Valley, Lake Bell, James Spader, William Shatner, and Rhona Mitra in Boston Legal (2004)
Mark Valley, Lake Bell, James Spader, William Shatner and Rhona Mitra in Boston Legal (2004)Robert Trachtenberg/Abc-Tv/Kobal/Shutterstock

Boston Legal was Spader’s first starring TV role, but there was initially pushback to casting him. As series creator David E. Kelley recalled, “I was told that no one would ever welcome James Spader into their living room.” He was told that while people liked watching Spader in movies, “they will never let him in their own home.”

Similarly, several actors passed on the role of Reddington in The Blacklist before it went to Spader. In both cases, casting him paid off as the shows earned loyal fanbases. He also briefly joined the cast of the beloved sitcom The Office as CEO Robert California in 2011, following Steve Carrell’s departure.

Who is James Spader’s wife?

Spader currently lives in New York City with his longtime partner, Leslie Stefanson, an actress-turned artist who he met during the 2003 movie Alien Hunter. Prior to dating Leslie, James was married to set decorator Victoria Spader, 63, whom he met while working on the set of the film, Sex, Lies, and Videotape. The couple was married for 17 years before they split in 2003.

James Spader and Leslie Stefanson 'The Avengers: Age of Ultron' film premiere, Los Angeles, America - 13 Apr 2015
Spader with Leslie Stefanson at the Avengers: Age of Ultron premiere (2015)Broadimage/Shutterstock

What James Spader is doing next

The Blacklist kept Spader busy for a decade, and his most recent film role was in the 2015 Marvel blockbuster Avengers: Age of Ultron, in which he played the evil robot title character. The director, Joss Whedon, called Spader his “first and only choice” and said, “He’s got that hypnotic voice that can be eerily calm and compelling, but he can be very human and humorous.”

Now that The Blacklist is over, we don’t know what Spader will be doing next. In a profile in The Guardian he referred to himself as the kind of actor who doesn’t have a lot of “things in the pipeline” at any given time, saying, “Unless I’m showing up on the set and acting I prefer to have nothing to do with the actual business of being an actor.”

It’s likely that in the wake of The Blacklist ending, he’ll kick back with nights at the jazz club and return to the screen whenever he finds something that inspires him. Whenever that may be, we look forward to seeing what kind of weird and wonderful roles he takes on next.

Catch up with more your favorite actors here:

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