Top 5: The five greatest gangsta rappers of all time
(Credit: Hip Hop Hero)


Top 5: The five greatest gangsta rappers of all time

The hallowed brilliance of a hip hop ‘Top 5‘ is that it puts your mind to the test. Of course, picking out your favourite rappers or their favourite songs is easy. Usually, such selections roll of the tongue like sweat rolls off an athlete’s back. But, given the parameters of squeezing those selections down to just five, it means we have to engage a little extra part of our brains. Given a chance to pick out our favourite gangsta rappers of all time, we can remind ourselves of just how potent the genre is.

It may seem like an area of hip hop that is rooted in the golden age of the genre, and there’s a good reason for that, during hip hop’s march to the top of the music pile, it enjoyed a savagery that can only truly be comparable to punk rock. A refusal to conform and a desire to represent the life that surrounded the rappers and artists below encouraged them to create visceral, vibrant, and, ultimately, violent music.

In the late 1980s and early ’90s specifically, the notion of gangsta rap began to infiltrate the mainstream. Thanks in part to the aforementioned brutality, the subgenre has quickly become one of hip hop’s most beloved. Whether it’s because the imagery and songs created are directly related to the audience’s life or, perhaps more prominently, the tracks about gangbanging, shooting guns and defending your zip codes offered a piece of Hollywood-esque escapism. Guns, money and glamour.

However, the reality for most of these rappers was far from glamourous. Most of the artists in the list below were a part of real-life gangs before they made it in hip hop. It means that the art they were creating was directly lifted from the reality that surrounded them. Originated on the West Coast, as time has moved on, the East Coast has also produced its fair share of gangsta rap legends.

The subgenre has exploded and given a foundation to much of what hip hop has become. While it may seem contradictory to rely on such a brutal genre to break into the mainstream, it was these artists’ ability to ruffle conservative feathers that ironically brought their style to the masses. But, who are the five greatest gangsta rappers of all time?

Top 5 greatest gangsta rappers:


Okay, so we’re cheating a little bit on this one. Grouping the potent rappers in N.W.A. into one entry is a way for us to celebrate the individuals that created one of the best rap groups of all time. Of course, Dr Dre and MC Ren can be regarded as originators of the genre, but it was their counterparts, Ice Cube and Eazy-E, that really drove the point of gangsta rap home.

Eazy-E is, without a doubt, the most notorious gangsta rapper of all. The artist was a gangbanging long before he ever stood close to a microphone, and it was this fearsome refusal to be anything other than “real” that attracted Dre to the artist in the first place. Then there is Ice Cube, who perhaps typified the group and the gangsta rap genre when he said during a famous press conference: “Our art is a reflection of our reality.”

This sentiment can be heard throughout the group’s discography with their debut album Straight Outta Compton a paint-by-numbers gangsta rap rulebook.

Tupac Shakur

Naturally, gangsta rap would be nowhere near as prominent today without Tupac Shakur. There is simply no doubt that Tupac Shakur‘s legacy will remain untarnished for decades to come. The rapper wasn’t just a landmark lyricist or extremely gifted performer, he was, the voice of a generation, the leading light of his field and, like many heroes before him, he is remembered as an icon.

But, just as iconic as his progressive politics, was his commitment to “thug life”, a statement he had tattooed across his stomach. The icon may have been killed when he was starting to reject the notion of being a gangsta but he was slain thanks to a typical street dispute.

Across his songs and albums, Tupac never shied away from being a gangsta and he spoke of violence as easily as he did social injustice. It is a perfect combination that makes him one of the best to ever do it.

Wu-Tang Clan

It’s hard to underestimate just how important the Wu-Tang Clan were to the evolution of hip hop. Concepts like ‘hardcore hip hop’ and ‘posse cuts’ had been firmly established within the genre, but the late 1980s East Coast hip hop world mainly was populated by alternative groups like De La Soul and A Tribe Called Quest.

Meanwhile, out in Compton, California, a new group brought a harder, more aggressive, and more streetwise version of hip hop into the mainstream. To call N.W.A. controversial would be underselling it: this was a group whose most famous song was a direct attack on the police and got them a disapproving letter from the FBI. Never before had anyone in hip hop inspired so much enthusiasm, fueled so much rage, and attracted so much attention.

The Wu-Tang Clan didn’t need to prove their authenticity: a collection of friends and family members from the Stapleton Houses projects of Staten Island, the Wu created their own world of ‘Shaolin’, complete with violent altercations, drugs, chess, and kung fu references. Stepping into Enter the Wu-Tang (36 Chambers) felt like stepping into an alternate universe, with its murky production and radical verses that found nine MCs, all bringing a different vicious style.

The Notorious B.I.G.

The other side of the explosive Tupac coin, Biggie Smalls, aka The Notorious B.I.G., was one of the biggest gangsta rappers on the East Coast. As well as being routinely seen as one of the few rappers who really lived the lifestyle he was rapping about, Big’s position as a former Brooklyn hustler has always leant weight to his work.

Though his feud with Tupac will undoubtedly define his legacy, Big and the West Coast rapper were thick as thieves at one point. However, as their discussions turned into disses, their verbal assaults turned into something more violent.

When the news of Biggie Smalls, aka The Notorious B.I.G.’s death, hit the airwaves, it left an entire generation of fans stunned into silence. Biggie’s impact on the growth of hip hop is immeasurable, and, in 1997, he was perhaps the brightest light in the world, proving to transcend culturally and genre divides at ease.


Beginning life in the Wild West Coast, Ice-T was always an underground rapper of serious intent. Displaying a complete refusal to conform to any path laid out for him, T has remained one of the most influential voices in the genre. As well it should be, the paper can easily be seen as one of the genre’s forefathers.

His album Rhyme Pays was drenched in gangsta rap imagery and even got the glorious accolade of becoming the first hip hop album to gain the “explicit content” warning label. Naturally, such a glowing endorsement set Ice-T up for mainstream success.

Never a part of a single gang, Ice-T was affiliated with both the notorious Bloods and Crips that dominated the hallways of his Crenshaw high school. He sued this reality to create art that transcended the confines of hip hop and made Ice-T into a pioneer.