Updated 03/14/2023 at 12:40 p.m. ET:
For some reason, gangsters in movies and on television are always popular. People are just infatuated with someone who doesn’t take orders from anyone and does what they want, even if it hurts others around them.
Think about it, how come popular characters in fictional entertainment like Succession and Empire have gangsta personas? Gangsters intrigue us.
Some of the actors have even taken home Oscars for their incredible roles in the film.
Rodney – Baby Boy
I don’t have enough fingers on my hands to count how many times I’ve seen this hood classic. Although Snoop Dogg has acted in plenty of movies and TV shows, he always just comes across as his normal self.
Levar – Get Rich or Die Tryin’
“You know you fucked up right?” I know Bill Duke did not utter that line in this movie, but it’s something about his delivery that’s always frightening and the same could be said for his acting in Get Rich or Die Tryin’.
Sugar Ray – Harlem Nights
I mean what else is there to say? It’s Richard Pryor, the greatest comedian ever, in the classic 1989 film, Harlem Nights. Of course, he’s on this list.
Big Meech – BMF
This show hasn’t reached iconic status yet. But, it’s pretty legendary that Lil Meech is portraying his real father in the show BMF. It’s not hard to believe, he looks just like him.
Deebo – Friday
Yes, I know Deebo was just a neighborhood bully on a bike, but would you be brave enough to tell him that he’s not a gangster?
Frank Lucas – American Gangster
Was anyone cooler than Denzel Washington in American Gangster? Just like he does in all of his roles, Denzel immediately became the coolest gangster ever when he portrayed the 1970s crime boss.
Jules Winfield – Pulp Fiction
Surprisingly, Samuel L Jackson’s performance as Jules Winfield in Pulp Fiction garnered him his only Oscar nomination in 1995. But, if he was going to only be remembered for one role, it was this one. He was easily the most terrifying and entertaining aspect of this movie. His “Big Kahuna Burger” monologue is still one of the most amazing scenes in cinema history.
Tommy “Buns” Bundy – Belly
Nas as Sincere in Belly was great. But DMX was the one who truly was the star of this movie. While watching the movie, it really doesn’t feel like he’s acting, it just looks like he’s being himself.
Cleo – Set it Off
This robbery move isn’t necessarily the most “gangsta” on this list, but if there was one character who embodied gangsterism, it was Cleo. The way she went out at the end of this movie was Tony Montana-esque.
Doughboy – Boyz n the Hood
“They either don’t know, don’t show, or don’t care about what’s going on in the hood.” That iconic line came from the 1991 film’s most iconic character, Doughboy, who just happened to be played by one of the hottest rappers of the time, Ice Cube. Despite, that introspective quote, he was the most ruthless character in the movie.
O-Dog – Menace II Society
Despite all of the acting Lorenz Tate has done, this is still his most iconic role. I love the relationship between O-Dog and Caine in this film, even if it didn’t end well for both of them by the end of the movie.
Foxy Brown – Foxy Brown
One of the most beautiful actresses ever often played ruthless characters. In Foxy Brown, Pam Grier is cold-blooded in this story of revenge.
Coffy – Coffy
Similar to Foxy Brown, Coffy is also a story of revenge and features the always-gorgeous Pam Grier.
Nino Brown – New Jack City
Wesley Snipes was the man in the 1990s. Jungle Fever, White Men Can’t Jump, Passenger 57, Blade. These were all legendary movies for Snipes, but his most legendary was his role as Nino Brown in New Jack City.
Birdie – Above the Rim
All of 2pac’s movie roles are iconic. Juice, Poetic Justice, Gridlock’d. But, as a big sports fan, I always love his performance as Birdie in Above the Rim.
Alonzo – Training Day
“King Kong ain’t got shit on me!” I mean what else is there to say? Yes, I know he’s a cop in this film, but his actions would say otherwise. This film gave Denzel Washington his second Oscar overall and is only one in the Best Actor category.
Mitch – Paid in Full
The early 2000s were good for Mekhi Phifer. He was great in O, Paid in Full, 8 Mile, Honey and many more, but he was at his best in Paid in Full. Don’t let the tears in the above pic fool you, he was as ruthless as any other character in the movie and the way he went out in this movie still pisses me off to this. day.
Rico – Paid in Full
I wonder why Com’ron never did any more movies after his role as Rico in Paid in Full? Yeah I know he was the antagonist of the movie, which viewers didn’t discover until the end, but he still did a great job at being arrogant and unlikeable.
Marilyn “Madam” DeVille – All the Queen’s Men
We didn’t forget about the ladies. Eva Marcille portrays a strong businesswoman who uses all of her power to stay at the top of the nightclub world. She will do whatever it takes, even if it will cost her her life.
Li’l Dice – City of God
If you haven’t seen City of God, I highly recommend that you do. This Brazilian gangster was ruthless as a damn child and straight terrifying as an adult.
Avon Barksdale – The Wire
The Wire is the greatest TV show of all time and has a couple of iconic gangstas in it. One of my favorites was Avon Barksdale, who was portrayed by Wood Harris. He had his morals and always believed in following the “rules,” but would take anyone out that got in his way, even if it was a close friend.
Stringer Bell – The Wire
For many fans of The Wire, after they watch the show for the first time, Stringer Bell is one of their favorite characters. He’s smart and good-looking so I get it. But after a second watch, fans realize how ruthless and in some cases naive he is. To this day, the rooftop scene between Stringer and Avon is still the best television scene ever.
Marlo – The Wire
In a show filled with brutal and cold-blooded characters, Marlo was the most callous. He just didn’t care. If they were seen as just a tiny threat, he would take them out. It didn’t matter if it was a security guard at a liquor store or the head of another drug operation.
Snoop – The Wire
While Marlo was the brains behind the Baltimore drug trade, Snoop was the muscle. Whenever he wanted someone taken out, Snoop was normally the one doing it. I still have nightmares of her shadow at the playground.
Omar – The Wire
Omar is the best character on the greatest TV show of all time. Portrayed by Michael K. Williams, Omar was the most quotable character on the show, “Come at the king, you best not miss, “It’s all in the game though, right?” the quotes just never end. Just watch the above clip that should tell you everything you need to know about how Omar was perceived in Baltimore.
Franklin Saint – Snowfall
No, I will not be arguing about Snowfall vs. The Wire. But I will acknowledge that Damson Idris is excellent as Franklin Saint. The fact that this British actor has perfectly gotten down as a West Coast accent is still insane to me.
Bumpy Johnson – Godfather of Harlem
Forest Whitaker’s portrayal of real-life gangster Bumpy Johnson in the Godfather of Harlem is something to behold. But, it shouldn’t be a surprise, after all, Whitaker has an Oscar of his own.
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