15 Morally Gray Characters That Leave A Lasting Impression

American actor Clint Eastwood on the set of ‘The Good, The Bad and The Ugly.’

Corbis via Getty Images

Sometimes it is fun to root for the bad guy. However, if the work is done incredibly well, you may even have to ask yourself, “Wait, are they actually the bad guy?” Morally gray characters allow audiences to think about the nature of right and wrong and even think about their own ethical codes. In many ways, morally gray characters are more true to life than perfectly good heroes and entirely evil villains. Real life is colored by shades of gray and people with complex motives and emotions. Morally gray characters can bring a level of realness or relatability to media.

What Qualifies As Morally Gray?

There isn’t an exact definition for “morally gray.” Most audiences and readers will know it when they see it. However, the trope boils down to characters who are not fully good or evil. It is similar to being morally ambiguous but often connects more to direct actions and motivations. Morally gray characters can be the heroes, villains or even side characters in their stories as long as the character exhibits both positive and negative qualities or actions.

Morally Gray characters overlap with antiheroes. However, there are some differences between the two tropes. Many antiheroes are on redemption journeys, and while morally gray characters can be redeemed, it isn’t as common in the trope. This list focuses explicitly on literature and film; however, ethically gray characters exist in many types of media (and are often heavily featured on TV).

15 Unique Characters With Morally Gray Tropes

Morally gray characters allow the audience to examine their own ethics and beliefs. They are shaped by the ethos of society and often mirror the ethical debates that permeate the larger culture when done right. Morally gray characters also create nuance. Their inclusion allows us to see flawed heroes and understandable villains. While morally gray characters exist in all genres, they are extremely common in superhero media, psychological films, fantasy and gothic literature and other genres that explore ethical themes.

A list like this is hard to write. There are so many characters in literature and film. Furthermore, moral grayness is a product of the society in which it is written or produced. Morally gray characters are a mirror of the current societal morality. For example, in the past, queerness and homosexuality have been tied to morally gray characters and themes. However, as society has more or less started to embrace LGBTQ+ characters, their grayness has faded. Similarly, older works often look at vainness, hedonism and adultery, while more modern works look at violence, betrayal and selfishness. Gender and sexuality also shape this discussion over time. This list takes a broad approach to moral grayness as well as the works considered. Importantly, when it comes to the ranking, this list looks at the quality and how morally gray the character is instead of the work as a whole.

15. Captain Louis Renault, Casablanca (1942)

Not all of the best morally gray characters are the main character. While many characters in Casablanca are emotionally and even morally complex, the only really gray character is relatively secondary: Captain Louis Renault, as portrayed by Claude Rains. Casablanca follows Rick, a nightclub owner whose life is complicated when he decides to help a leader of the Czechoslovak Resistance, Victor Laszlo, escape Morocco and the Nazis, even though Laszlo is traveling with an old flame of Rick’s, Ilsa Lund.

While Renault is a morally corrupt policeman who even works directly with the Nazis, he also shows a backbone in moments where it matters, leading Rick to famously say to him, “Louis, I think this is the beginning of a beautiful friendship.” Even in moments of heroism, Renault feels entirely out for himself. Directed by Michael Curtiz, Casablanca stars Humphrey Bogart and Ingrid Bergman. It is an American film classic that was added to the Library of Congress in 1989. Here’s where you can find Casablanca.

14. Dr. Frankenstein, Frankenstein (1818)

Not to be confused with Frankenstein’s Monster, Victor Frankenstein is a central character in Mary Shelly’s 1800s Gothic horror classic. There are many versions and adaptations of Frankenstein, and the doctor can range from a monster/madman to a touching creator. However, the original novel is fairly different than many of its adaptations. In the original text, Victor turns to the study of science after the death of his mother.

The novel follows a scientist who creates a humanoid creature. While Dr. Frankenstein flees from the creature out of fear, they meet again, and the monster tries to force Victor to create a female creature for him. Victor has ethical concerns, and he destroys the female, which leads to bloodshed. The mad scientist archetype is usually associated with moral ambiguity, and Frankenstein is really where this archetype originated. Here is where you can find Frankenstein.

13. Charles Foster Kane, Citizen Kane (1941)

Citizen Kane follows a ruthless, wealthy man and a mystery left after his death. Many entries on this list celebrate their characters’ ambiguity. Citizen Kane is a little different. The film reads more as a cautionary tale about how ignoring morality leads to personal rot. The film’s plot was loosely based on the life of William Randolph Hearst. Citizen Kane follows Charles Foster Kane from his boyhood to the end of his life after his morally gray choices leave him wealthy but alone.

Directed by and starring Orson Welles, the film was controversial upon its release, given that its main character was based on a powerful man who was still very much alive at the time. Even so, it was nominated for nine Academy Awards. The film has a wonderful plot and message, but it is also notable for its technical advances, especially the extended use of deep focus (a technique where the foreground, mid-ground and background are all in sharp focus). Here’s where you can find Citizen Kane.

12. Travis Bickle, Taxi Driver (1976)

While the vigilante has become a more celebrated and heroized trope in media, almost all vigilantes fall under the morally gray umbrella. Arguably, the best portrayal of a vigilante in film comes from Martin Scorsese’s classic psychological drama, Taxi Driver. The film follows Travis Bickle, a veteran, whose insomnia drives him to patrol the streets of New York as a vigilante.

The film stars Robert De Niro, Jodie Foster, Albert Brooks (in his feature debut), Harvey Keitel, Leonard Harris, Peter Boyle and Cybill Shepherd. The film caused some real-life controversy after it inspired John Hinckley Jr. to attempt to assassinate Ronald Reagan in 1981. However, the film is still considered a classic and one of the most significant films ever made. Here’s where you can find Taxi Driver.

11. The Man With No Name, The Good, the Bad, and the Ugly (1966)

The Man with No Name appears in three Spaghetti Westerns that make up Sergio Leone’s “Dollars Trilogy:” A Fistful of Dollars (1964), For a Few Dollars More (1965), and The Good, the Bad and the Ugly (1966). While all three films are Western classics, The Good, the Bad and the Ugly is often touted as the best of the series. The character is heavily influenced by the titular character in Akira Kurosawa’s 1961 samurai classic, Yojimbo (the first film in the series, A Fistful of Dollars, is arguably an unauthorized remake of Yojimbo). However, when it comes to morality, The Man with No Name feels more dubious than Toshiro Mifune’s take on the classic samurai.

As portrayed by Clint Eastwood, The Man with No Name is a drifter motivated by money and his warped sense of justice. In The Good, the Bad and the Ugly, The Man (also nicknamed Blondie in this film) joins a tenuous partnership with a Mexican outlaw to find reward money and buried treasure during the American Civil War. The film also stars Eli Wallach and Lee Van Cleef. While it is now considered a classic, the film originally premiered to poor-to-mixed reviews. While it is a beautifully directed film, not everything ages well in it. Salon included it on their list of “Seven Totally Racist Films Your Parents Love,” and it does have a central character in Brownface. Here’s where you can find The Good, the Bad and the Ugly.

10. Tyrion Lannister, A Game of Thrones (1996)

While it is the first book in George R. R. Martin’s A Song of Ice and Fire series, many will find 1996’s A Game of Thrones novel synonymous with a later TV show of a similar name. There are some differences between the book and the TV show; however, Tyrion Lannister appears in both, and in both, he appears as morally gray. He isn’t at his most duplicitous in the first book, but still acts in his own self-interest and preservation throughout the work. Honestly, many of the characters in the series could have found a home on this list.

A Game of Thrones has a pretty complex plot; however, it follows House Stark, House Lannister and the North as political tensions rise in the fantasy world of the Seven Kingdoms of Westeros. Most of the characters in the (currently) five-book series are morally complex, and the series doesn’t shy away from themes like sex, power, religion, corruption and moral ambiguity. Here’s where you can find A Game of Thrones.

9. Emma Bovary, Madame Bovary (1857)

Many of the most famous morally gray characters are male, and (at least in more modern works) their reasons for moral ambiguity usually stem from violence. However, when it comes to morally gray characters (especially in classic works), their ambiguity often comes from vanity or promiscuity. These characters are also often tragic. One of the most famous characters that fits this archetype is Emma Bovary in the classic French novel Madame Bovary by Gustave Flaubert.

The novel follows a young woman who craves romance and excitement in her life, leading her to adultery and suicide. Emma Bovary is a tragic figure who may not even seem fully morally gray to modern audiences. However, in 1850’s France, her hedonism shows a lack of moral character. Madame Bovary is a beautiful and heart-wrenching classic novel. Here’s where you can find Madame Bovary.

8. The Kim Family, Parasite (2019)

Parasite is a morally complex film. There are almost no characters that are not at least a little morally gray. The comedy/thriller from Bong Joon-Ho follows the Kims, a low-income family, who con their way into working for a wealthy family in Seoul. The film will have audiences rooting for a family that lies, scams and even poisons a woman.

Parasite stars Song Kang-ho, Lee Sun-kyun, Cho Yeo-jeong, Choi Woo-shik, Park So-dam and Jang Hye-jin. It was the first Korean film to win an Oscar; it won four, including Best International Feature Film and Best Feature Film (making it the first film to win both categories). Here’s where you can find Parasite.

7. Hamlet and Claudius, Hamlet (C. 1600)

William Shakespeare’s Hamlet is a play about moral ambiguity, and that is reflected in its two main characters. From just the plot synopsis, it may seem clear-cut: Claudius kills Hamlet’s father to steal the throne of Denmark and marry the queen. However, the play is about greed, revenge and uncontrolled emotions. Claudius is the villain, but he shows a surprising amount of remorse and guilt over his actions, while Hamlet is consumed by revenge.

While the play is quintessential high school reading, it is best seen live. There are also many adaptations of Hamlet, from the 1948 Laurence Olivier version to the 2014 Bollywood version Haider. Here’s where you can find Hamlet.

6. Jef Costello, Le Samouraï (1967)

Le Samouraï is one of the chicest films ever made, and its protagonist, Jef Costello, drips coolness. The film is very French and very 1960s, but that is what makes it so good. It follows Costello, a hitman, who must evade police and his own crime bosses after a hit on a nightclub owner. Portrayed by Alain Delon, Costello is a hitman, but you still side with him as he navigates the criminal underworld and evades police.

Directed by Jean-Pierre Melville, it also stars Nathalie Delon, Cathy Rosier and François Périer. Le Samouraï was wildly influential on the action/hitman genre. The character feels very connected to later films, especially by directors like Martin Scorsese and Quentin Tarantino. Here’s where you can find Le Samouraï.

5. Dorian Gray, The Picture of Dorian Gray (1891)

The Picture of Dorian Gray is a classic work of Gothic Literature. Written by Oscar Wilde in 1891, the book follows Dorian Gray, a man who exchanges his soul for eternal beauty and youth. The work is about narcissism and hedonism, and Gray is a vessel to examine these themes along with another character, Lord Henry “Harry” Wotton. While Lord Henry lacks moral character, Gray must create his own moral compass throughout the work.

The book itself was seen to be morally questionable, and Wilde had to remove sections to avoid violating British laws guarding public morality. However, contemporary reviewers still found it shocking. A shorter, novella-length version of the work was originally published in 1890 in Lippincott’s Monthly Magazine. A novel version was published the following year. In 2011, a new uncensored version, The Picture of Dorian Gray: An Annotated, Uncensored Edition, was published by the Belknap Press. Here’s where you can find The Picture of Dorian Gray.

4. Jack Sparrow, Pirates of the Caribbean: The Curse of the Black Pearl (2003)

There are five Pirates of the Caribbean movies, and they range sharply in quality. However, the first film is surprisingly good for an action movie based on a 1960s amusement park ride. While there is a lot to love about The Curse of the Black Pearl, the standout is arguably Jack Sparrow as played by Johnny Depp. Sparrow is a quintessential morally gray character. Throughout the series, his allegiances and motives are in a constant state of flux. There is a chaos that surrounds his character as he is often acting only in his best interest (with moments of vague chivalry and caring for others… though there are few).

Pirates of the Caribbean: The Curse of the Black Pearl follows Sparrow, a drunken pirate captain, a governor’s daughter and a blacksmith as they must break a powerful curse and steal a remarkable ship. The film also stars Keira Knightley, Orlando Bloom, and Geoffrey Rush. It was nominated for five Oscars and earned Depp a SAG Award. Outside of the films, Sparrow became a cultural phenomenon. Here’s where you can find Pirates of the Caribbean: The Curse of the Black Pearl.

3. Adrian Veidt, Watchmen (1986-1987)

There are multiple film and TV versions of the classic graphic novel, Watchmen. However, the book is superior to arguably all of them. Originally published as a 12-comic run from 1986 to 1987, Watchmen comes from writer Alan Moore and artist Dave Gibbons. The graphic novel follows a complicated alternative history as members of a group of former superheroes are murdered in the lead-up to a mass destruction event.

One of the central heroes is Adrian Veidt, codenamed Ozymandias. Including him on this list is a bit of a spoiler (further SPOILER ALERT) since it is revealed that he is also the villain of the story. While Veidt is behind the deadly plot, his motivation is a sincerely held vision of world peace. One of the best things about Watchmen is its trove of complex characters; for a book about superheroes, there aren’t always clear-cut villains and heroes. It is a beautiful and influential work in the comic book genre. Here’s where you can find Watchmen.

2. Loki, The Avengers (2012)

From Harley Quinn to Erik Killmonger to Magneto, superhero films often have great morally gray villains. One of the best is Tom Hiddleston’s take on Loki in the MCU. The character has appeared in many Marvel films, including Thor (2011), The Avengers (2012), Thor: The Dark World (2013), Thor: Ragnarok (2017), Avengers: Infinity War (2018) and Avengers: Endgame (2019). The character bounces between hero and villain, which is fitting given that he is based on a Norse god associated with mischief, deception and shape-shifting.

The MCU’s version of Loki is morally grey as he is usually out for himself. However, he is arguably at his most villainous in 2012’s The Avengers. Marvel’s first team-up movie follows a group of heroes who must stop Thor’s brother Loki from using a powerful object to take over Earth. Directed by Joss Whedon, it stars Robert Downey Jr., Chris Evans, Mark Ruffalo, Chris Hemsworth, Scarlett Johansson and Jeremy Renner. It was the first Marvel movie to make over $1 billion, and it led to three direct sequels: Avengers: Age of Ultron, Avengers: Infinity War and Avengers: Endgame. Moreover, the blockbuster defined what the next ten years of superhero movies would look like. Here is where you can find The Avengers.

1. Lady Eboshi, Princess Mononoke (1997)

Princess Mononoke is a beautiful animated film from Studio Ghibli. Directed by Hayao Miyazaki, the film is set in the Muromachi period (around AD 1400) and follows an epic war between kami (forest deities) and humans. One of the central characters in this war is Lady Eboshi. She’s a complex character. She wants the best for her people and even fights for the women and the sick. However, her plans for bettering her world come at an environmental and spiritual cost. Princess Mononoke is a wonderfully nuanced film that doesn’t shy away from moral ambiguity.

Princess Mononoke is arguably the film that established Studio Ghibli outside of Japan. It was a critical and box office juggernaut, holding Japan’s box office record for domestic films until 2001’s Spirited Away. It was also the first animated film to win the Japan Academy Film Prize for Picture of the Year. Here’s where you can find Princess Mononoke..

Bottom Line

The line between right and wrong can often be thin, not only in media but also in life. Morally gray characters let us to explore the realities of morality and our own ethical codes.

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