Steal from the rich to give to the needy. – A tale of thievery as olde as tyme, and one that gains the affections of the masses through radical do-goodery. But that’s a fairytale. Real life is more complicated than just that, and by real life, we mean real fictional Italian jobs and Makatomi Plaza takeovers. We can now fall for these anti-heroes and anti-villains because of their complex backstories, righteous goals, and the writing/talent that brings them to life. They may be stealing a priceless ring or staking out a First Brooklyn Savings Bank, but in the process, their characters are also stealing our hearts. 

Hans Gruber (Die Hard)

Hans Gruber (Alan Rickman) is a villain through and through, and a really good one at that. For Hans, there’s no backstory (other than the fact that he’s had a good education) or explained purpose (the takedown of corporate greed is a sham), yet he is a fully-fledged villain that stands with just as much charisma as our shoeless hero Bruce Willis. He is somehow a genuine delight to behold as he sneeringly takes hostage the 30th-floor office Christmas party and mercilessly begins to off them. 

Rickman did the lofty, intelligent, upturned-nose thing so well in this role that he’d routinely struggle to get out of doing roles in the same veins (Harry Potter, Galaxy Quest). He’s just that kind of fantastic character actor whose antithetical presence to his protagonist counterparts tends to offer half of the appeal, and Gruber is no exception. 

Danny Ocean (Ocean’s Eleven)

First of all, George Clooney. Second of all, the rest of the cast. And the cherry on top of it all is the brilliant writing that caters to all the characters (and their actor’s) talents, culminating in a crockpot of ensemble heist movie wall of fame glory. 

Clooney is the definition of leading man material. It thus leads his merry band of mischievous misfits with skillful prowess as they infiltrate Tony Benedict’s vault, not for the money, but as Rusty (Brad Pitt) comes to find out when she walks down the stairs, for love.  Okay, the money probably didn’t hurt, either. But ‘love’ being the motivation is just icing on an already too-delicious-to-resist cake. The script and the ensemble are so strong that we’d fall head-over even without the romantic inspiration. With that additional motivation, a protagonist thief simultaneously seals the deal and opens the vault to our affections. 

Veronica (Widows)

First of all, Viola Davis. Second of all, Viola Davis. And lastly, the cherry on top and the whole freakin’ sundae, still- Viola Davis. The movie is a breath of fresh air in the concept itself, inviting a group of widows (ah, yes, there’s the title) to team up and participate in a heist movie with more meat than your average popcorn flick typically serves. 

Davis commands the screen, just as we love and expect, as Liam Neeson’s wife, who has to repay his gang’s debt after his last robbery, which leads to their death. Davis has the same lead character quality as the aforementioned Clooney and similarly: ropes together her team, hatches the scheme and carries out a very satisfying heist, all while being just simply stunning. It’s long overdue, considering it was Davis’ first lead role in a three-decade-long career.

Benjamin Franklin Gates (National Treasure)

Who doesn’t love a nerdy, scholastic hero that needs to steal a historical artifact because it belongs in a museum? Because Indiana Jones was momentarily out of commission, our stand-in was Benjamin Franklin Gates. He’s an excellent ol’ boy on a mission- to take the fiery torch of passion from Nicolas Cage’s own words: “- to steal the Declaration of Independence.” 

Why does he need to steal the Declaration of Independence? – To keep it from being stolen. A solid plot for a solid movie brought to life and made eternal like our founding father’s document by Cage, the father of our love for committing to the role 100%, no matter what. 

An additional shoutout needs to be given to Cage’s warm-up thief run of 50 cars in one night in Gone in 60 Seconds.)

Gollum (The Lord of the Rings) 

The complicated creature, initially beginning in The Hobbit as the hobbit Smeagol, fell instantly under the ring’s spell, going so far as to murder his cousin Deagol to be its sole owner. As the legend goes, nearly 500 years of being obsessively consumed by ‘the precious’ morphed his form from a friendly hobbit to a “wretched” and “vile” cave-dwelling creature.

The brilliance in this character, captured using earlier mo-cap technology by the spectacularly transformative Andy Serkis, is the duality in his personality. Gollum is both to be feared and never trusted, but also pitied. Serkis crafted such tender moments that make us feel deeply for the torture that the ring has induced on swallowing his life and yearn for his return from its evil grasp. 

John Bridger (The Italian Job)

Why Donald Sutherland gets to hold the chief thief status while only getting a fraction of the screen time is partly due to his film history. In The Italian Job, he marries the sweetness of his role in Ordinary People with the gentlemanly command of his Casanova. He’s perfectly cast as the godfather of this remake gang. While Marky Mark offers an adorable Jr. replacement, Sutherland gives the pinnacle of crookery for all his followers to aspire to. 

He’s worldly, slick, sly, and a learned shepherd to his flock. Even though he’s murdered (2003 spoiler alert) early on in the movie, he is the type of presence we can still feel throughout the film. We want his death avenged because we quickly grew an umbilicus to him in those brief moments while he was still alive. 

Wanda (A Fish Called Wanda), 

In A Fish Called Wanda, the multifaceted scream-queen Jamie Lee Curtis swam more profound into the comedy stream as the fishy femme fatale with every other character on her hook in their 13-million pound jewelry heist. It’s a very ‘Cleesey’ (John Cleese) comedy, and Curtis splishes and splashes with the best of her fellow cast mates proving to be the optimal combination of zany and seductive. 

Her sense of humor goes beyond the script for the character, and Cleese credited her for improvising many of the lines that ended up in the film. She also says she purchased toothbrushes for each male costar on the first day of the shoot, saying, “You know, because it’s gross! You’re just gonna be making out with all these strange people. So I asked them to go brush their teeth.” 

Sal (Dog Day Afternoon)

John Cazale is the character actor who always seems so closely tied to the inside of his character’s soul that you lose sight of the actor. The 39-year-old Cazale was cast to play the should-have-been 18-year-old Salvatore “Sal” Naturale only because of this pure talent. In Dog Day Afternoon (directed by Sidney Lumet and based on an actual incident), our leads aren’t heroes, villains, or anti-heroes.

The stressful situation of a bank heist that shouldn’t be is the antagonist. We want everyone to make it out okay. As we roll through the ill-fortuned bank job, our dreading comes in time with Cazale’s increasing anxiety, boiling up like a steaming kettle. He’s not the type of loose canon fortified with terrifying iron strength. That’s how our fear of Cazale can be mixed in a cocktail of empathy. We can see that he’s teetering on a glass shelf that could shatter at any moment, and we’d give anything if we could protect him.