All-Time Greatest Rappers

The rap game has changed dramatically over the years, going from its humble origins with DJs spinning records at parties for MCs to rap over to its status as popular music today, with many rappers holding the title of being some of the richest and most famous artists in the world. In that time, many great streetwise poets have proven their abilities to come up with insightful lyrics and clever wordplay while flowing over the hottest beats.

Many different styles have emerged, and many rappers claim they deserve to be included in conversations about who is the greatest of all time. Such a distinction is nearly impossible to pick, but we have chosen four who are serious contenders for the top spot. Read on four for the four greatest rappers of all time.

2pac

Tupac Shakur was born and brought up in New York City and moved to Baltimore as a young teenager, yet the rapper, having relocated to the Bay Area in his late teens and later came to Los Angeles, is perhaps the greatest West Coast rapper of all time and was the region's major player in the East-West rap wars. In some ways we never got to know what he was truly capable of, as he was shot in a drive-by when he was just 25, a death that will be forever shrouded in mystery and controversy over who did it, why they did it, and if it ever actually happened. 

However, his death just added to his legend, as did his massive catalog of unreleased music that allowed for a steady supply of new Tupac albums to still come out even after he died. While it is his tragic untimely death and his legendary beefs that many know him for, his music, which was always introspective and poetic while still oozing with his “thug life” swagger, is what will make him remembered by future generations.  

Eminem

Hailing from Detroit, Marshall Mathers was from the beginning much more than just a “white rapper,” and his unique style and deeply personal lyrics lit a fire with audiences, making him one of the most successful artists of all time. He got his big breaker later than the average rapper, with his breakthrough major label debut “The Slim Shady LP” not releasing until he was in his late 20s, but his experience coming up in the battle rap scene (as dramatized in the fictionalized but still biographical film “8 Mile”) made him an unstoppable force on the mic. 

In the early 2000s, Eminem was America’s most transgressive cultural figure, and his ability to consistently shock and make headlines was a sign of our pre-social media era naivete. In the beginning, many wrote him off as someone selling shock value gimmicks, but hundreds of millions of albums and countless awards later, Eminem has proven himself to be one of the greatest and most important artists of his generation, and he left a mark on the world of music by greatly expanding the audience for rap music.

The Notorious B.I.G.

“Biggie Smalls is the illest,” rapped The Notorious B.I.G. on the song “The What.” That was the ninth song on Biggie’s debut album “Ready to Die,” and by that point it was already hard to disagree with him. B.I.G. only had that one album to release in his lifetime, and then his sophomore work Life After Death ironically came out just weeks after he was gunned down in a drive-by on a visit to Los Angeles.

Getting killed in a highly mysterious shooting when he was just 24, his life has many parallels with Tupac Shakur’s and the two will always be inextricably linked, both because of their deaths less than a year apart, their status in the hip hop coastal wars with Biggie representing the East Coast, and their status as two of the greatest who have ever hit the mic. Biggie died on top, but you still get the sense that he was just getting started, and it is easy to imagine that if he had lived, the Brooklyn icon would still be at it outrapping the competition decades later. 

Jay-Z

In 2019, Jay-Z was awarded the title of hip hop’s first billionaire, and he had quite the (hard knock) life getting to that point, starting from a rough childhood growing up in a Brooklyn housing project without a father present and an adolescence that saw him selling crack and getting shot at. He spent nearly a decade trying to make it as a rapper before his debut “Reasonable Doubt” dropped when he was 26, and the rest is history, with the rapper seeming to get bigger with every album to becoming one of the biggest names not just in hip hop but in all of music. 

Now, music practically feels like a side project for Shawn Carter, whose business empire includes music streaming, sports bars, clothing brands, artist management, champagne, film production, and more. When he does put out music, though, he always proves that he hasn’t missed a step, staying ahead of trends and showing the new generations how it is done. He is also half of the entertainment industry’s greatest power couple, and he and his wife Beyonce have even put out a collaborative album and toured together.