10 Rappers We Underestimated

We'll admit it, we slept on these guys. But you probably did too.

January 30, 2014

Image via Complex Original

Over the years, there have been a few rappers who we just knew were going to be big stars from the moment we first heard them. From legendary acts like The Notorious B.I.G. to more recent artists like A$AP Rocky, it was obvious that these rappers were born to be stars. But it takes the perfect blend of lyricism and style, not to mention one hell of a back story, to achieve longevity in the rap game. It's why so many rappers aren't able to sustain a career that lasts more than one or two albums.

Because of all this, there have also been quite a few rappers over the years who we didn't think were going to be stars the first time we heard them. In certain cases, it was because of their sound. In others, it was their sketchy (or not-so-sketchy!) past. There are even a few rappers who we never thought would even have a hit song, but somehow they did. But whatever the reason, there have been lots of rappers who have surprised us by overcoming their perceived flaws and launching successful rap careers.

Here are the 10 Rappers We Underestimated Greatly.

Written by Chris Yuscavage (@ChrisYuscavage)

Drake

Why we underestimated him: We didn't think an actor-turned-rapper from Canada who sung as much as he rapped could ever become the hottest rapper in the game.

When he proved us wrong: When he dropped his critically-acclaimed mixtape, So Far Gone, in 2009 and proved that he could rap just as well as he could sing.

We obviously weren't the only ones who jumped on the Drake bandwagon back in '09. Since then, he's released three platinum albums and sold more than five million albums total. He's also set a new record by hitting No. 1 on the Billboard Hot R&B/Hip-Hop Songs chart 11 times. And he's ranked at or near the top of every "Hottest Rappers/MCs" list that's been released in recent years on a consistent basis. So much for all those preconceptions we had of him five years ago.

Rick Ross

Why we underestimated him: We didn't think a guy who stole his rap moniker from drug kingpin "Freeway" Rick Ross and his rap style from Young Jeezy would survive being exposed as a former correctional officer.

When he proved us wrong: When he followed up his first two albums, 2006's Port of Miami and 2008's Trilla, by demonstrating marked improvement on the mic on 2009's Deeper Than Rap.

To be honest, we're still a little bit surprised that Ross was able to overcome the C.O. scandal and continue his career, despite the major hit that his credibility took after the controversy. But he has consistently enjoyed success ever since 2009's Deeper Than Rap. He beat the once invincible 50 Cent in a battle, he dropped great albums (Teflon Don), great mixtapes that might as well be albums (Rich Forever), and he made game-changing songs ("B.M.F."). Not to mention he also found time to make MMG one of the hottest labels in the game. Who needs a solid back story when you make great music?

Childish Gambino

Why we underestimated him: We didn't think anyone would take a sitcom actor/writer who used a Wu-Tang Clan name generator to create his rap name seriously.

When he proved us wrong: When he showed everyone that his rap career was not a joke by dropping his debut album, Camp, in 2011.

It took six mixtapes, an EP, and an album to do it, but Gambino finally forced people to take him seriously as a rapper. His debut album peaked at No. 11 on the Billboard 200 chart and has sold more than 240,000 copies to date. And his most recent effort, Because the Internet, did even better, charting at No. 7 on the Billboard 200 chart and selling almost 200,000 copies. The best part is, if there's still anyone who doubts his mic skills all you have to do is link them to this video and they'll become true believers. The craziest part is that Gambino's best days as a rapper are probably still ahead of him.

2Pac

Why we underestimated him: We didn't think that one of the dancers/hype men for the group Digital Underground would go on to become one of the greatest rappers of all-time.

When he proved us wrong: When he launched a solo career in 1991 and dropped his debut, 2Pacalypse Now, an album that tackled all sorts of social issues like poverty, racism, and teen pregnancy.

Though 2Pac's first two solo efforts, 2Pacalypse Now and 1993's Strictly 4 My N.I.G.G.A.Z., didn't launch him into the spotlight immediately, he transformed into a star within just a few years. In 1995, his third album, Me Against the World, topped the Billboard 200 chart when it was released, as did his Death Row Records debut, All Eyez on Me.

To date, he has sold more than 75 million albums total (including his posthumous releases) and is obviously considered one of the all-time rap greats. And to think, he used to be one of the guys who played the background in a rap group...

Lil Wayne

Why we underestimated him: We didn't think he'd have much of a career after Cash Money fell apart and we definitely didn't think he'd eventually become the Best Rapper Alive.

When he proved us wrong: When he dropped his 2004 album, Tha Carter, and then followed it up by going on an absolute tear on the mixtape circuit over the next five years.

Prior to Tha Carter, Wayne had scored a handful of hits both on his own and as a member of Cash Money's Hot Boys. We thought he was cool, but no one thought he was on his way to becoming the beast he eventually became. Wayne took things to another level in 2004 by releasing the first of eight consecutive albums to land on top of the Billboard Rap Albums chart.

He has sold more than 15 million albums during his career, scored dozens and dozens of Top 40 hits, and many of his mixtapes—including 2006's Dedication 2, 2007's Da Drought 3, and 2009's No Ceilings—are considered classics in their own right. All that for a guy we once thought would never contribute anything more to hip-hop besides the phrases "bling bling" and "drop it like it's hot."

Kanye West

Why we underestimated him: We didn't think that a brash, overconfident hip-hop producer who favored polo shirts and Louis Vuitton backpacks and compared himself to Michael Jackson could actually ever compare to Michael Jackson.

When he proved us wrong: When he released his debut album, The College Dropout, in 2004 and it was immediately hailed as one of the best rap debuts of all time.

Looking back now, it's amazing to think that there were many labels out there who wrote Kanye off. Although his debut is the highest-selling album of his career, every single solo project that Kanye has released since then, including last year's Yeezus, has debuted No. 1 on the Billboard 200 chart. He has sold more than 20 million albums. Kanye has changed the rap game in immeasurable ways and influenced nearly every single rapper out today. And to think, they thought Pink polos would hurt the Roc.

DMX

Why we underestimated him: We didn't think that a dog-loving MC from Yonkers who called his debut single, "Born Loser," would ever amount to much.

When he proved us wrong: When he turned his love for canines into his 1998 hit single, "Get At Me Dog," and followed it up by releasing his gritty debut album, It's Dark and Hell Is Hot.

X was, is, and probably always will be, rough around the edges. But people loved his aggressive style of rapping in the late 1990s—after labels basically spent all of the early '90s fronting on him. But when he did finally break through, he had a major impact; his first five albums all debuted at No. 1 on the Billboard 200 chart. To put that into perspective, Beyoncé is one of the only other artists to ever have the first five albums of her career debut at No. 1. Not bad for the "born loser."

2 Chainz

Why we underestimated him: Lil Wayne was the main reason his group—Playaz Circle—scored a hit with "Duffle Bag Boy." Also, his name was Tity Boi. Nuff said.

When he proved us wrong: When he changed his name to 2 Chainz, released his stellar mixtape, T.R.U. REALigion, and created a whole new identity for himself.

2 Chainz did such a good job of rebranding himself in 2012 that some casual rap fans didn't even realize that 2 Chainz was Tity Boi. T.R.U. REALigion was full of fun rhymes and lots of personality (even the mixtape's cover, which featured 2 Chainz using a urinal, got a laugh out of us). And thanks to the new moniker that he created, 2 Chainz' debut solo album, Based on a T.R.U. Story, debuted at No. 1 on the Billboard 200 chart. To say 2 Chainz has made a huge transformation as a rapper would be an undastatement.

Flo Rida

Why we underestimated him: We were 100% sure he was going to be a one-hit wonder.

When he proved us wrong: When he continued to put out hit after hit.

Pop quiz: Name a Flo Rida album. Does Mail on Sunday or Only One Flo ring a bell? Eh, not likely. But Flo Rida—who had one-hit wonder written all over him after "Low" went 7-times platinum—has been able to put out a strong of hit singles since 2007, and 11 of them have earned platinum distinction from the RIAA.

We're not going to sit here and tell you that we love every one of them or that we're huge Flo Rida fans (if anything, it pains us to call him a "rapper"). But you have to respect what this guy has been able to do. Plus, we don't see him stopping anytime soon.

Jim Jones

Why we underestimated him: We didn't think Cam'ron's former hypeman would release a single that reached No. 5 on the Billboard Top 100 chart.

When he proved us wrong: When he made "We Fly High" in 2006.

True, Jones has struggled to maintain the same success that he enjoyed back in the mid-2000s. But outside of Cam, he's been the most successful member of The Diplomats, both in sales and on the Billboard charts.

All five of his solo albums have debuted in the top 20 on the Billboard 200 chart. He struck gold with "Pop Champagne" in 2008, just two years after "We Fly High" took off and eventually went platinum. And he's done it all through a partnership with E1 Music (formerly known as Koch Records), meaning he hasn't had the same kind of label backing or support as anyone else on this list. That's pretty impressive for a former hype man who wasn't even the second best rapper in his crew. (Peace Juelz!)