Ranking the top 20 greatest and most successful rappers of all time

Pimp C might not have been the most successful rapper, and he might not have had the longevity (he died prematurely after an overdose on lean), but his influence is undeniable – Frank Ocean and Big Sean count themselves as disciples. For proof of his genius, you don't need to look any further than "Big Pimpin'," the Jay Z track he and fellow U.G.K.-er Bun B featured in. In just eight bars, Pimp C snatches ownership from Hov. His delivery was so sick nasty, he didn't even feel like he had to be in the music video for the song. But more importantly, Pimp C posed one of hip hop's greatest rhetorical questions: "Now, what y'all know about them Texas boys?"

The man who's a.k.a.'s include "Dark Gable" and "Blackanova" is largely credited for bringing the braggadocio and swagger to hip hop. It's true, and not only that, but Big Daddy Kane did it with clever rhymes and smart one-liners. 

It makes sense that Slick Rick is seen as a pioneer of hip hop as storytelling device. The British-born MC is, after all, quite the character – the bling, the eyepatch, and his penchant for doing voices come to mind.

How good was Big Pun? So good he only needed to release one album to enter the conversation for the greatest rappers of all time. His debut "Capital Punishment" is basically a double album full of banging tracks that featured Big Pun rapping as if his life depended on it. Like others on this list, Christopher Lee Rios passed away well before his time (he died of health complications stemming from his weight). Not only was he one of the greats, but Pun was also the first Latino rapper to burst out into the mainstream.

Nowadays, DMX is thought of as a nostalgic curiosity, a formerly popular artist who's become a novelty because he did a rap version of "Rudolph the Red-Nosed Reindeer." This is baffling, as DMX is one of the rawest and hardest MCs to ever live, and from 1998 to about 2003, the Ruff Ryder was arguably the most dominant and successful rapper during that period. His first five albums, (all released during this period) reached the top of the Billboard Chart, a feat surpassed only by Beyonce. 

There isn't another rapper – dead or alive – who is most closely associated with the streets than the Houston native. Scarface has embodied the "rap song as documentary" ethos going back to his days with Geto Boys – "My Mind is Playing Tricks on Me" to this day is the greatest hip hop song about struggling with mental issues ever recorded – and hasn't stopped since.

The Doggfather's longevity and success is a testament to his brilliance. The LBC rapper was there for the early days of G Funk – Snoop revitalized Dr. Dre's career, who was feeling uninspired and burned out after leaving N.W.A. – and he was here for hip hop's invasion of pop music. 

Being forced to pick your favorite member of the Wu-Tang Clan is what I imagine parents feel when they're asked who their favorite kid is. The diplomatic answer is to say that they're all special in their own way – very true when it comes to Wu-Tang. But really, every parent has a favorite, and in my case it's Ghostface Killah. After "Enter The Wu-Tang (36 Chambers)," GFK put out "Iron Man" and "Supreme Clientele," and he collaborated with Raekwon on "Only Built 4 Cuban Linx." If anyone deserves the "Ironman" moniker, it's most definitely him.

Here's a partial list of rappers who have cited "The Kool Genius of Rap" as a direct influence: Jay Z, Raekwon the Chef, Nas, Biggie Smalls, Mobb Deep. The Corona, Queens MC is one of the progenitors of hardcore rap, and his delivery can best be described as machine gun firing complex, multi-syllabic rhymes.  

Who is he? THE MC! In sound clash, KRS-One is the Blastmaster, one of the OGs of boom bap hip hop. As part of Boogie Down Productions, KRS-One held it down for the Bronx, and as a solo artist, he's been one of the greatest and most authentic voices in hip hop history.

Marshall Mathers is proof that the way in which you deliver a rhyme is oftentimes more important than what's actually being said. Eminem's biggest criticism has always been the substance of his lyrics – they can be sophomoric, homophobic, sexist – which, is extremely fair. But his flow is unlike any other. It's so concise, clever, clean, and caustic. It's genius.

Chuck D is the political preacher of hip hop. His booming delivery and socially conscious lyrics make his rhymes the hip hop equivalent of a Martin Luther King, Jr. sermon or Malcolm X speech. Straight up, Public Enemy is the most important rap group in the history of the genre, and Chuck D is a huge reason why.

Many people argue that Ice Cube ruined his hip hop legacy after becoming a mainstream actor that made children's movies. Many people are idiots. N.W.A. is one of the most culturally significant groups in all of music, period. But when a young O'Shea Jackson decided to leave the group and go solo in 1989, they lost the edge that made them dangerous. Ice Cube would go on to make some of the most sucessful records on the '90s after going solo – his three first albums, "AmeriKKKa's Most Wanted," "Death Certificate," and "The Predator" all went platinum.

When Kendrick Lamar was a kid, he saw Tupac perform on the roof of Compton swap meet while recording the music video for "California Love." At that moment, a young Kendrick told himself that he'd be his generation's Tupac. He's accomplished that goal. When his first album, "Section.80," came out, people thought he had potential. By the time "Good Kid, M.A.A.D. City" came out, K-Dot had been upgraded to being the future of hip hop. With "To Pimp a Butterfly" an "DAMN.," Compton's finest proved that the future was already here.

Andre Benjamin pretty much ended the West Coast/East Coast beef that had dominated hip hop through much of the '90s when he and fellow Outkast member Big Boi took the stage at the 1995 Source Awards to accept the "Best New Artist" trophy. "The South got something to say," a defiant Andre 3000 told the crowd. With that statement, not only did Three Stacks redefine hip hop as being more than just a bicoastal affair, but he also put Atlanta on the map. Without Andre 3000 and Big Boi, there would be no Migos, no T.I., and no Killer Mike. 

Jay Z has been one of the most dominant artists – not just rappers, artists – of the last 25 years. His mastery of the mic is nearly unparalleled, and his verbal dexterity is so brilliant that the Songwriters Hall of Fame had to induct him in 2017 – the first time a rapper has been given that distinction – in order to maintain their credibility. Hov made "Reasonable Doubt, The Blueprint," and the "Black Album." What more proof do you need?

If you were to ask your favorite rapper who his or her favorite MC is, nearly all of them would say it's Rakim. They'd probably tell you that what they love most about Rakim is how easy and effortlessly he made rapping out to be. And it is... if your name is Rakim. For a lot of rappers on this list, the first time their minds were blown by the concept of internal rhymes was probably the first time they listened to Eric B. & Rakim's "Paid In Full."

Nas put out "Illmatic" when he was 19-years-old. Nasir Jones could've walked away from the game after dropping the greatest rap album of all time (this isn't open for debate) and he would still be a contender for "greatest MC of all time." But he didn't. Instead, Nas went on to make "It Was Written" and "Stillmatic" – both instant classics – and "The Lost Tapes," the gold standard on what a compilation album should be like. As if that weren't enough, he also ethered Jay Z when the latter tried to come for him.

In his book, "The Rap Yearbook," author Shea Serrano claims that even if Biggie Smalls wasn't the greatest rapper of his era, he was certainly the most fun largely because he rapped about life as if his hardships were yours, as if his wins also belonged to you. Honestly, that's the best summary of the Brooklyn rapper. A lot of people claim the Notorious B.I.G. is the greatest rapper in history because no other MC has connected with them quite like Biggie did, and you know what, that line of argument goes a very long way when it comes to the "greatest ever" conversation.

Come on, guys. It's not even close. No disrespect to the other MCs on this list, but Tupac Shakur is on a whole 'nother level all by himself. Not only was he one of the most commercially successful rappers of all time – his estate still makes millions despite the fact that he's been dead for more than 20 years – but he was prolific, too. He didn't make music, it just flowed out of him – his last album, "The Don Killuminati: The 7 Day Theory" was written and recorded in a week. Pac also made not one, but two iconic West Coast anthems – "California Love" and "To Live and Die in L.A." – and he singlehandedly went to war with just about every one of your favorite rappers, Nas and Biggie come to mind, and walked away the winner. Oh yeah, and "Hit 'Em Up" will forever be the greatest diss track ever recorded. If all this doesn't make someone the greatest ever, I don't know what does.