There have been a few characters in television history who left a lasting impression on the public, often transcending traditional archetypes of heroes and villains, one of which is Raymond Reddington, the criminal mastermind from TV’s greatest characters as well as one of the most intriguing protagonists.
What made him such a memorable presence, however, is not just his multifaceted nature but his sheer genius, his evolution from fugitive to FBI informant, and his unwavering devotion to those he loves. People are drawn to complex yet highly intelligent anti-heroes- figures with a fractured yet undeniable moral com. And for the fans of The Blacklist, there are many characters who, despite their unique peculiarities, share Reddington's allure.
10 Michael Westen
Burn Notice
Michael Westen, the central character of Burn Notice, shares several traits with Raymond Reddington. Westen is a former CIA spy with a complex history who becomes suddenly blacklisted from the system without any explanation. Despite becoming a private spy, he refuses to let go of his past, using his skills to investigate his burn notice. A master of espionage, Michael is highly skilled at manipulating and adapting to any circumstances.
Like the protagonist of The Blacklist, he has also adopted a mentality of "the end justifies the means."
However, Michael's primary goal is to help those in need, which is a stark contrast to the more self-serving motives of Raymond Reddington. Rather than a criminal turned FBI hero, Westen is a vigilante attempting to follow his own idea of right or wrong. However, despite having mostly noble intentions, he also operates within a grey area. Like the protagonist of The Blacklist, he has also adopted a mentality of "the end justifies the means."
9 Alan Shore
Boston Legal
The truth is that part of what made Raymond Reddington such a legendary figure in the crime genre was the hypnotic performance of James Spader. With his penetrating gaze and self-assured smirk, Spader exudes the sense that he knows far more than anyone else can even begin to comprehend—a gift shared by both Reddington and another of his iconic roles, Alan Shore. As a consequence, both the characters end up standing out in their respective shows.
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Alan Shore might be a lawyer and thus operates within the legal system, but that same position gives him a keen knowledge of the criminal world. This allows him to exploit the fallacies of the law to his advantage- and not always in the most ethical way. Because of their quick wit, manipulative skills, and the fact that they are interpreted by the same actor, the two figures share the same irresistible albeit slightly wicked charm.
8 Walter White
Breaking Bad
One of the most groundbreaking and complex figures in television history, Walter White shares Raymond's deceptive and cunning nature. A cancer-stricken teacher who slowly evolves into a meth kingpin to secure his family’s future, the protagonist of Breaking Bad captured the hearts of millions with his tragic descent into moral ambiguity. Despite his increasingly questionable actions, however, Heisenberg remained a sympathetic figure throughout the show, earning iration from some along the way.
Although his actions often contradicted his intentions, Walter never completely lost his empathy and continued to care deeply for his family and his partner. Like Raymond, he could be incredibly protective of those he loved. Furthermore, despite his late start in the criminal world, he proved highly effective due to his unparalleled resourcefulness and willpower. However, unlike Red, Walt lacked a cold, controlled demeanor, which ultimately led to his downfall. Perhaps, had he started earlier in life, before being diagnosed with terminal cancer, he could have had more time and lucidity to adapt to the criminal underworld.
7 Thomas Shelby
Peaky Blinders
Thomas Shelby, the charismatic leader of the Peaky Blinders gang, is another anti-hero who shares traits with Raymond Reddington. The head of the Shelby family, Thomas is a complex and morally ambiguous man who navigates the brutal world of crime in early 20th-century Birmingham, all while attempting to maintain his strict code of honor and protect his loved ones. Cillian Murphy's performance, like Spader's, brings a chilling intensity to the character.
Similarly to Red, Thomas is able to thrive in the criminal environment, manipulating most situations to his advantage and always thinking ahead.
Both characters captivate the public with their layered personalities and unpredictable moves. And both are fiercely protective of those who are in their inner circles. However, whereas Shelby's influence and political game are limited to Birmingham, Raymond is one of America's most wanted criminal masterminds.
6 Saul Goodman
Better Call Saul
A man who hides behind the law, Saul Goodman is another mastermind who expertly manipulates the system as he finds convenient. Like Jesse Pinkman once said: “You don’t want a criminal lawyer. You want a criminal lawyer." If they were to forces, Saul and Raymond would probably be invincible. Both incredibly resourceful and quick-witted, they could use their knowledge of their respective fields to achieve any goal.
Like Red, Saul is an effortlessly captivating anti-hero who might not always play by the rules but still conquers the viewer because of its unpredictable nature and infinite nuances. There is an emotional depth to the characters that makes them inherently sympathetic. However, Reddington and Saul are also significantly different. Albuquerque's most prominent lawyer does not share the stoic and unshakable facade of the FBI's cleverest informant and is more likely to fall prey to his doubts and fears. With his more honest vulnerability and over-the-top behavior, Goodman is often underestimated—a disastrous mistake.
5 Sherlock Holmes
Sherlock
One of the most brilliant characters on television, and in the history of literature, Sherlock deserves to be mentioned when discussing iconic figures like Reddington. The investigator of Baker Street is a relentless truth-seeker, always chasing after the most absurd crimes to uncover what might be hidden before less vigilant eyes (and not-so-sharp minds). The version of the character played by Benedict Cumberbatch in BBC's Sherlock is the perfect example for this comparison.
It is true that, compared to Red, a former crime lord, Sherlock has always fought with the good guys. However, that does not make him the morally superior hero his allies might perceive him to be. He might not have the villainous backstory of America’s most wanted man, but he has nonetheless proven himself capable of bending his morality to achieve his means. Sherlock's unparalleled reasoning skills and keen attention to detail might force him into an endless cat-and-mouse game with Raymond, where their comparable talents would make for a fascinating rivalry.
4 Berlin
Money Heist
Berlin might have been one of Spain's most wanted criminals with slightly sociopathic tendencies, but he was also, before that, the devoted brother of The Professor. His character was the heart of Money Heist, and as much as the series never ceased to be intriguing, it was clear it would never be the same after his death. With his calculated nature and effortlessly charming persona, he was not so dissimilar to Raymond.
The two anti-heroes share many qualities (and flaws). Aside from the impeccable performances of their actors, Berlin and Raymond are incredibly intelligent and sarcastic. They conceal their occasionally disturbing ruthlessness under seemingly sophisticated and polite behavior. Despite their cruel streak, they have a firm code of honor, valuing loyalty and camaraderie above all, while also standing by their strong albeit warped idea of justice. Furthermore, although it has repeatedly been questioned, Berlin, like Raymond, deeply cared for the few people close to him.
3 Benjamin Linus
Lost
The most intriguing character of Lost, Benjamin Linus, might not be the criminal mastermind stereotype that Reddington represents, but he clearly possesses the sheer genius, strategic mind, and moral ambiguity needed to compete with him. As the cryptic leader of "The Other", he is a highly intelligent and motivated individual who manages to give a hard time to the survivors of Oceanic Flight 815. And, although vague and mysterious, his reasons are always present.
Like Reddington, Ben's deceptions and enigmatic history are so well-crafted that it becomes challenging even for the public to see through him. Furthermore, the two figures start as more traditional villains, only to gradually evolve into anti-heroes, earning the loyalty of the fans over time. However, unlike Raymond, most of Ben’s actions are revealed to be driven by personal trauma and insecurities, investing the character with a vulnerability that makes him more human compared to the more stoic protagonist of The Blacklist.
2 Tony Soprano
The Sopranos
The original anti-hero, the man who paved the way for other TV protagonists to lean into their darker impulses, Tony Soprano is the worthy ancestor of Raymond Reddington. As a key figure and, later, boss of the New Jersey-based mafia environment, Tony is a layered protagonist, capable of unspeakable cruelty and moments of surprising vulnerability. Interpreted by James Gandolfini, he remains one of the most legendary characters in history.
Similarly, the two characters demonstrate exceptional competence in their respective worlds, which earns them the respect of the public.
Tony made it possible for inherently cruel characters to emerge as the heroes of the story, provided their arcs follow a specific formula. For instance, although they operate outside the law and harbor sociopathic inclinations, these characters cannot—and should not—be entirely devoid of empathy, as is the case with the Soprano boss and Reddington. Similarly, the two characters demonstrate exceptional competence in their respective worlds, which earns them the respect of the public. Both Tony and Raymond walk the line between iration and fear. However, although their stories aren’t immediately sympathetic, Tony comes across as more relatable.
1 Neal Caffrey
White Collar
Before Raymond Reddington, another redeemed criminal stole the heart of the public. Neal Caffrey is a world-class con artist and thief, who uses his charm and intelligence to survive and thrive in the criminal underworld. Like Red, he is forced to end up working alongside the FBI. Because of the similarities between their backstories and circumstances, many consider The Blacklist to be the White Collar's replacement TV show. However, James Spader's series is far darker than its inspiration.
Aside from the more lighthearted tone of White Collar, the protagonists of the two stories also share some significant differences. Caffrey is less ruthless than Reddington and far more reluctant to cross moral lines after all, his crimes are limited to forgery and deception. Nevertheless, similarly to the criminal mastermind of The Blacklist, the former con man is also amiably witty, unpredictable, and willing to operate in gray areas.
The Blacklist
- Release Date
- 2013 - 2023-00-00
- Network
- NBC
- Showrunner
- Jon Bokenkamp
Cast
Dianne WiestRuth Kipling
Raymond 'Red' Reddington
WHERE TO WATCH
- Directors
- Andrew McCarthy, Michael W. Watkins, Bill Roe, John Terlesky, Donald E. Thorin Jr., Christine Moore, Kurt Kuenne, Terrence O'Hara, Adam Weisinger, Mahesh Pailoor, Karen Gaviola, Stephanie A. Marquardt, Steven A. Adelson, Daniel Willis, Matthew McLoota, Bethany Rooney, Joe Carnahan, Paul A. Edwards, Alex Zakrzewski, David Platt, Jean de Segonzac, Jono Oliver, Michael Zinberg, Paul Holahan
- Writers
- Jonathan Shapiro, Kelli Johnson, Brandon Margolis, Daniel Knauf, Dawn DeNoon, Aiah Samba, Dave Metzger, Justine Neubarth, Dave Thomas, Kim Newton, Vincent Angell, David Merritt II, Chap Taylor, Daniel Voll, Elizabeth Benjamin, John Zinman, Wendy West, Anthony Sparks, Jim Campolongo, Kristen Reidel
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