As readers and writers, we’re drawn to grey characters. We can’t help it. And what’s greyer and more complicated than a hit man with a romantic side, conscience and/or high moral standards?

Sure, killing is bad. Killing isn’t a choice we can approve in real life.

That said, we don’t exactly love watching accountants (though The Accountant is a fun movie about a highly atypical accountant), angelic social workers, or extremely ethical and by-the-book lawyers on screen.

We want characters that can kick ass, draw blood and inflict pain on those who deserve it. We also want them to have a side that knows to protect the innocent.

Now, the movies  I’ve picked are mainly from the 90s or more recent. Don’t hesitate to add your favorites in the comments, from whatever era they might be. I’d love to check those movies out.

But here’re some of the first hitmen I and some of my dear friends love and remember.

• Léon starring Jean Reno (1994)

Ah, the first gentle hitman most of my generation has been exposed to. A middle-aged contract killer saves a girl whose family is killed, and he goes on to protect and mentor her. Of course of all the relationships here, the one between Léon and his young friend (12-year-old friend, to be exact) is the most ambiguous and controversial.

Was it a father/daughter thing? Was it romantic? It kind of looked that way to some extent.

But either way, Léon keeps her alive. I need to rewatch this as it has been awhile. Oh, and Gary Oldman is the baddie.

 

• Assassins starring Sylvester Stallone (1995)

The 90s is the era where a lot of my favorite movies come from. A lot of entertaining and dearly rewatchable movies came out of that decade. Assasins is one of my favorite action films to revisit.

First, the casting is awesome and weird:

Sylvester Stallone as the “cuddly” hitman, a gorgeous but wacky Antonio Banderas as the “villain” hitman, and Julianne Moore as an introverted, cat-loving and smart hacker. But it somehow works in that 90s way.

Stallone’s character deserves to be here because he has a strong sense of morality: He doesn’t kill the innocent (which unsurprisingly doesn’t include other hitmen who might or might not be his friends).

Banderas’ character will kill anything and anyone if it means he’ll get paid or even pleasure and convenience. And boy, does he love to kill.

So when Stallone fails to kill Moore and chooses to protect her instead, a stubborn Banderas is sent after to finish the job. Moore and Stallone become partners in crime (in getting the killers off their back, not killing), while also liking each other. And really, if you’re a cyber-criminal who doesn’t like most people, an almost-retired hitman who has a romantic side does sound eligible. Oh, and he likes cats!

 

• Grosse Pointe Blank starring John Cusack (1997)  

 

John Cusack plays a hilariously neurotic hitman with issues. The pace (and the comedy) picks up when he needs to go to his high school reunion and kind of falls for an old classmate in the process. There’ll be a lot of shooting and blood before this guy can find his happily-ever-after.

 

• John Wick starring Keanu Reeves  (2014)

I’d argue John Wick is the most realistic action film here. Our hero sure does kick too much ass, and we need to suspend some disbelief, but at least he runs out of bullets and gets hurt and stuff.

But the style, pace, and fight choreography make John Wicirresistibletable addition to the genre. The character seems tailor-made for Keanu Reeves: silent, reserved, and smooth; deadly only when disturbed.

John Wick is the perfect romantic hero too: he is a bad-boy-turned-good when he falls in love and leaves the business of killing. (I didn’t see anything bad besides the job, but come on, having been a hitman for the mob is surely enough to label him bad). And he doesn’t want to return. He grieves quietly for his deceased wife with the adorable dog she gifted him and gets the adrenaline pumping by driving his beloved car.

But when his former boss’s clueless, entitled, and stupid excuse for a son kills his dog, beats him up, and steals his car, he is understandably mad and decides to kill him. It’s not his fault the boss decides to send an army after him and increases collateral damage.

But can we get behind a gorgeous, charismatic and kickass retired killer who is avenging the memory of his wife and getting rid of the world of some very bad people in the process? Absolutely.

 

• Shoot ‘em Up starring Clive Owen (2007)

This is the funniest film on the list and also has the best soundtrack. It might be the most entertaining too. Anyway, my judgment is a bit biased. I love a good mindless entertainment flick. I also love rock music, Clive Owen, and Paul Giamatti. So… The movie might change how you feel about carrots, though. You’ve been warned.

So we have a homeless-looking, carrot-eating and very competent killer who happens to help a woman give birth. When the mother is killed, he saves the baby and just tries to survive with the baby through the whole movie. At some point, he needs the assistance of former flame/prostitute ……. who provides some motherly love for the little one, and a totally different kind of loving to our sexy hitman. 

 

• Crying Freeman starring Mark Dacascos (1995)

Frankly, I don’t like Crying Freeman as much as the others, but it has its own appeal. It’s based on a comic book, and the movie goes by comic book logic and physics, which is what makes this flick fun. If you don’t take anything seriously, you’ll probably have a better time.

But the hitman is gorgeous, and when he “confronts” his supposed victim/murder witness, she’s in her bathrobe and in her bedroom. She was quite taken by him, having already painted an impressive and sizable portrait of the killer. Now, I should mention that she’s not exactly the most rational and life-loving person on the planet, having lost her parents to another hitman and blamed it on herself for about two decades.

So her reaction to about to be killed by this guy is lying on the bed and closing her eyes. His reaction to this is taking his clothes off and getting on the bed with her, and then well…you know.

Of course, he has to do some naked killing after their hot session, but it all comes with the territory. But at least these killers had the decent timing of coming after they had sex, so they didn’t give our hitman, called Crying Freeman, the chance to prove he could kill people while he’s giving his object of lust/love an orgasm. (Yes, I’m referring to the Shoot ‘em Up scene between Clive Owen and Monica Belluci.)

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There should be a sexy and conscionable contract killers list for female characters, but honestly, I couldn’t think of anyone besides Nikita. And I’m more familiar with the TV series where she wasn’t exactly a contract killer.

So please do mention your favorite female killers that fit the context. Who are your favorite deadly but cuddly hitmen?