The Best Heroic Thieves and Why We Love Them

When someone mentions the word "thief," who do you think of first? 

There are many characters from all over the world spanning the course of history that fit the idea. You know, the charming, fearless criminal full of wit and charm? That's the one!  

If you're a fiction aficionado, you may think of characters that fuel pop culture legends. Gamers know Sly Cooper, Nathan Drake, and Edward Kenway by their distinct styles. Novel and comic readers know masterful criminals like Arsène Lupin and Selina Kyle have captured hearts for years. Thieves have a certain allure about them that's present in both modern entertainment and throughout storytelling history.

Countless factors draw us toward those willing to take on daring feats and pickpocket society's most discreet. Maybe it's the fact that our favorite thieves subscribe to the "steal from those who deserve it" ideology. Maybe they're stealing back a usurped family heirloom. Or, maybe we root for them because professional thieves appreciate a good challenge—we all like a character with some guts.

No matter why we love them, these fictional characters are nothing short of awe-inspiring. They outsmart any target, lift any valuables, and infiltrate the most secure places on earth. High-stakes heists are nail-biting when you care about the characters involved. Plus, any way you slice it, effective thievery takes a certain amount of refined skill and improvisation. Add in some motivating vigilantism, and you have a compelling plot that we can all find inspiring.  

This character archetype is also incredibly versatile. We can look back on seafaring tales and see real-life pirates dominating the scene. In the world of fiction, we immediately recognize Marvel's iconic Black Cat and DC's Catwoman. Let's examine some of the most notable (or notorious) thieves to lay claim to the thieving throne:

BLACK CAT

Felicia Hardy is one of Marvel's most iconic female thieves. To sum her up in her own words, "I'm not a hero. I'm a thief. Born a thief. Raised a thief. Will die a thief." Her father, a renowned cat burglar, always encouraged her to only aim for the best. She took this lesson to heart. Black Fox, her father's mentor, freed her from prison after she was arrested. She quickly became his new pupil, and after learning a good deal, Felicia donned the Black Cat costume. Her first mission was to break her father out of prison, which led to her meeting Spider-Man. The DLC in Marvel's Spider-Man explores part of their relationship via gameplay. 

CATWOMAN

Selina Kyle is an expert thief in DC Comics who regularly crosses paths with Batman. She has lots–and I do mean LOTS–of comic history. In the New 52, Selina learned to steal while in a group home. A while later, after getting caught stealing, she began work at the mayor's office. While there, she discovered a file stating that her identity was not what she believed it to be. Someone pushed her off a roof when she investigated further. Then, after she became Catwoman, she discovered those files had been wiped away. More recently, having more or less cast her villainy aside, she often operates as one of Batman's allies.

ASSANE DIOP

Assane Diop leads a Netflix show titled "Lupin," inspired by the iconic Arsène Lupin. Recognized as "​​the most entertaining criminal genius in literature," Lupin was first created by Maurice Leblanc. In fact, he rivals Sherlock Holmes in Leblanc's books. A reformed thief, the original Lupin is a criminal genius. Though he changed his ways and became a detective, his fellow police often suspect him and doubt his change of lifestyle. In the Netflix show, Assane Diop is a unique spin on the character. Lupin's mastery of disguise, extraordinary heists, and overall flair inspires him on his quest for revenge.

CARMEN SANDIEGO 

Thieves are even popular in edutainment franchises. Brøderbund's Carmen Sandiego is an expert thief as well as the leader of the Villainous International League of Evil. Carmen is constantly chased by the ACME Detective agency, and she also recently had a Netflix revival in 2019. This newer show presents her as the heroine aiming to take down V.I.L.E. (Villainous International League of Evil) Nice acronym, by the way.

SLY COOPER

A character inspired by Arsene Lupin, Sly Cooper adds his own spin to the thieving genre. Hailing from a long line of thieves, Sly Cooper makes a name for himself through sheer tenacity and creativity. Like Lupin, Sly spends most of his free time in Paris. When on the job, he uses clever wiles and expert techniques to pull off unbelievable heists against equally unbelievable odds. 

Sly and his team distinguishes themselves by stealing only from other thieves (the best of the best, of course). His antithesis, the fearless Inspector Carmelita Fox, is relentless in her pursuit of his capture. After spending years chasing his family's legacy, Sly realizes that not all legacies are diamonds once you crack them open. Some are best left buried. A tale of friendship, resilience, gravitas, and adventure, Sly's chapter in the book of fiction is a standout act. The series furthers his allure as a charming rogue while also establishing his own legacy. A legacy that may soon be resurrected, considering fans may be expecting another installment.

NATHAN DRAKE

Next in line is none other than Uncharted's Nathan Drake himself. Nathan doesn't exude a suave style like some of the other thieves. Let's be honest, a life spent searching for ancient civilizations like Shambhala and The Atlantis of the Sands doesn't exactly lend itself to a suit and tie. However, we do see him dress up a little in Uncharted 4. 

More of an improviser, Drake can talk himself out of almost any situation. And when words fail, he's a fairly accomplished brawler and marksman. As a thief, explorer, and history buff, he becomes one of the few people to set foot in ancient cities lost to time. In fact, by the start of the fourth Uncharted game, he has an attic full of archaic items and fond memories. After outmaneuvering his villains, he often leaves even the richest hidden civilizations empty-handed. Drake chooses instead to escape with something truly priceless: his and his companion's lives. That, and the knowledge that their most recent cataclysmic discovery is forever buried and out of prying hands. Seems pretty great to me!

CHLOE FRAZER

Chloe Frazer is more of a thief in the Uncharted games compared to the treasure hunter Nathan Drake. A woman of quick wit and an equally quick draw, she's a fan of improvisation and doesn't lack grit and fortitude. As a professional thief for hire, she has plenty of experience that leaves her skills in high demand. 

In fact, in The Lost Legacy, we see her steal a key item from the villain's headquarters in her quest to locate the Tusk of Ganesh. Throughout the game, Chloe works with Nadine Ross (from Uncharted 4) to find the priceless mystical artifact. The narrative addresses her character growth, loyalty, and newfound determination. No longer is she the Chloe who cuts her losses. Now, she refuses to walk away from what matters. Not to mention, she's known as "the best driver in the business," and there are more than a few allusions to that fact during the game's many driving sequences. 

EDWARD KENWAY

And who can forget Edward Kenway from Assassin's Creed IV: Black Flag? Pirates often evoke thoughts of robbery and violence rather than master thievery. We may be more apt to think about canon fire and the instantly-recognizable Jolly Roger than stealthy maneuvers. But pirates were no less accomplished in the looting department. Kenway is a Welsh-born privateer who became both a pirate and a member of the British Brotherhood of Assassins. I'm biased due to my love for pirate-related content, but of the many Assassin's Creed games I've seen, Black Flag is by far my favorite.

Why, oh why, do we love them so?

After all my research for this article, I've come up with a theory: we love thieves in entertainment because we all love to see the morally grey. Obviously, we speak about characters who are morally grey, here, not about characters or people who have done heinous, unforgivable acts. Definitely want to make sure that's clear. (Unless we're talking about Game of Thrones Jaime Lannister, at which point I would warn you not to get me started on how they massacred his TV redemption arc… but I digress.) 

A character with a skewed moral compass is just plain fun to see. Complicated backstories make characters more compelling. It sets them up to be able to make bold decisions that would cause someone used to walking the line to hesitate. Sometimes hesitation just isn't an option. 

Flawed characters like these are also more relatable and understandable to us. We can see ourselves in their motives, choices, and decision-making, and occasionally in their quest for redemption. There's more opportunity for exciting action, intriguing choices, and a complex plot because when morally grey characters run the show, they can mess some shit up! In the words of Henry Avery as presented in Uncharted 4, "I am a man of fortune, and I must seek my fortune."  Epic scenes and memorable lines don't fall out of the sky; someone's gotta get their hands a little dirty to stoke the fire.

With such a memorable group of characters across entertainment, the idea of the charming, daring thief won't be going anywhere soon. In a life of 9-5s, taxes, and piles of homework, it's nice to think of how far a little cleverness can get you. Thankfully, there are safer outlets for us flesh-and-bone mortals. You know, those of us who can't disappear in a smoke bomb, leap across mountaintops or don't know the difference between port and starboard. Yes, I had to look it up. This is a judgment-free zone. Isn't it? Isn't it?

Anyway, while I for one won't be stealing jewels and precious coins, I do plan to nick a few hours of gaming this weekend.  

Did your favorite thieves make the list here? Let me know who I missed in the comments!