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Hip-Hop Legends in Training: Five Artists On The Way To Legendary Status

Tupac Shakur: legend. Michael Jordan: legend. The first person to combine dough, sauce, cheese and pepperoni to create pizza: major legend. In the case of Comedy Central’s new animated series Legends of Chamberlain Heights, legendary comes in the form of benchwarmers Grover, Milk and Jamal of the Michael Clarke Duncan High basketball team, the Black Holes.

This trio of swag-challenged freshmen is determined to make high school history by any means necessary, from Grover’s pursuit of senior hottie Cindy to Jamal going all Walter White and concocting his own designer party drug, “Jamalies,” out of Milk’s mom’s stash of prescription pills.

Despite the crew’s formidable challenges (including Milk’s racist dad and Grover’s deadbeat brother), their boundless bravado and more than a little luck find them well on their way to actual high school legend status. Check out the story of these legends on Wednesdays (tonight) on Comedy Central and anytime on the CC app.

Achieving legendary status in the world of hip-hop is an equally challenging endeavor where many are called to the mic, but few are chosen to be graced with the moniker of rap legend.

In the current cavalcade of rap superstar wannabes stand a handful of MCs who’ve elevated above the rest and are well on their way to join the likes of Kendrick Lamar, J. Cole and Drake as the next generation of hip-hop legends.

Chance the Rapper

Like the leads of Legends of Chamberlain Heights, Chicago’s Chance the Rapper started his march towards legendary status as a high school student. After being suspended from his prep school for weed possession, Chance used the time off to craft his first mixtape, 10 Day, and start his steady ascent to star status. His second mixtape, the 2013 release Acid Rap, propelled him to the head of hip-hop’s emerging class of contenders and the title track landed on President Obama’s 2016 summer playlist. Sharing the spotlight with his boys, he directed attention to fellow Chicagoans Donnie Trumpet and the Social Experiment, a band in which he is just another member, with the critically acclaimed 2015 release, Surf, also a free download. He’s still humble enough to be a fan while looking out for his own legion of faithful followers (and sticking it to the man). Eager to give back, he uses his influence to look out for people in need, a sign of a true legend in the making. He’s also pretty good at dancing like an inflatable arm-flailing tube man. That has to count for something.


The latest in a long line of influential Atlanta rappers, Future got his start as part of the legendary ATL crew, the Dungeon Family. It was during those salad days when he earned with his moniker, since his style sounded like (wait for it) the future. After a slew of mixtapes, his debut album would feature his first collaboration with Drake, starting a big-money partnership that would eventually result in the pair crafting a joint album, What a Time to Be Alive. Blending his unique use of Auto-Tune with a slurring vocal style to psychedelic effect (a.k.a sounding like you’re twisted on a double-cup of actual “dirty Sprite”), Future’s immense influence in the world of hip-hop has already spawned a legion of similar-sounding artists (some would even say imitators) from the next generation of emerging MCs, most famously Brooklyn rapper, Desiigner, who crafted the biggest hit Future forgot to record, “Panda.” He’s blowing up arenas across the country with Drake on the massive Summer Sixteen tour, which keeps selling out as many shows as they can tack on to it. He’s had three No. 1 albums in less than seven months. He even named his son (with R&B singer Ciara) Future, setting him up for a pretty solid rap career of his own in the next 20 years or so. He’ll be the one calling Jaden Smith old in 2032. As long as daddy Future keeps getting the club turned up with banger after banger, he just might be hitting the road with his junior version around the same time. Now that’s legendary.


Coming straight out of Compton, YG is a straight-up gangsta. Like, an actual gangsta, being a renowned member of notorious West Coast street gang, the Bloods. He doesn’t use words that start with the letter C, because of the Bloods archrivals, the Crips. Hence, the title of his latest album: Still Brazy. You’ll certainly never catch him wearing the color blue, that’s for sure. He reps Compton’s legacy G-funk sound to the fullest, making music that directly references the likes of local legends like DJ Quik and Dr. Dre. He keeps it G no matter where he goes, unashamed to admit that the first time he pulled a gun was in a church. In YG’s world, it’s like the ‘90s never ended. Keeping it true to the rules of the street, the longer he can roll to the top of the charts as one of hip-hop’s most famous gang members, YG’s hood pass will remain intact while he becomes a bona fide legend in the world of hardcore rap.

Travis Scott

This Houston native has something in common with Grover from Legends of Chamberlain Heights. Where the animated character prays to his personal Jesus, NBA star Lebron James, Scott is famous for being a hardcore Kid Cudi stan. It motivated him to become a big-time rapper, and it wasn’t long before his skills had the likes of Kanye West and T.I. cluttering his inbox and trying to sign them. Being smart as well as good on the mic, he signed with both. “It’s cool because you get the best of both worlds,” Scott has said about his musical mentors. “You got both of these guys who are extremely super talented.” Yeah, that’s one way to describe being put on by not just one but a pair of rap legends. Now he has the clout to get Kid Cudi to guest on his most recent album, Birds in the Trap Sing McKnight, which debuted at No. 1 on the Billboard 200 despite being an Apple exclusive. It’s just another step towards becoming a hip-hop legend and having some emerging rapper in the future just trying to become the next Travis Scott. Having his alleged girlfriend Rihanna allegedly snatched back by Drake only ups his emo-god status.

A$AP Rocky

The leader of his very own one-man hip-hop Harlem renaissance, A$AP Rocky is the kind of guy you can say has got cat class and he’s got cat style. Since “just” being a rap superstar is so 20th century, Rocky has made a point of diversifying his portfolio, bringing his sartorial splendor to the game by blending streetwear and high fashion to showcase his status that’s gotten so large that the “only thing bigger than my ego is my mirror.” Working as a high profile model in campaigns for the likes of Alexander Wang and Dior Homme, Rocky has also found his way into the tabloids, thanks to persistent rumors that he’s currently dating Kendall Jenner (his ex-girlfriend is none less than the perpetually controversial Iggy Azalea). Breaking out with druggy anthems, “Peso” and “Purple Swag,” Rocky has flaunted both classic rock and psychedelic drugs as influences in his music, since there’s no reason Action Bronson gets to have all the fun. He’s already worked with a wide variety of producers, including Mark Ronson, Danger Mouse and Clams Casino, and even played a black JFK to Lana Del Rey’s Jackie O in her video for “National Anthem.” Combining his iconoclastic and ever-evolving style with a growing influence through the A$AP Mob collective, Rocky’s path to rap legend is looking pretty clear.

For more on achieving legendary status, be sure to catch Legends of Chamberlain Heights on Wednesdays (tonight) at 10:30/9:30c on Comedy Central and anytime on the CC app.

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Pandemonium Ensued

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An Untimely End

At the height of their popularity, B2K would announce their split on BET's 106 & Park in Jan. 2004 to the dismay of R&B fans everywhere. Omarion would later state that the decision was ultimately caused by the group’s mutual desire to seek out solo success. “It is true that B2K broke up but it’s not about me leaving or them leaving. It’s about us growing up and wanting to do our own thing,”  he told Jet magazine in 2004.

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If you weren’t one of the lucky thousands who got to catch B2K on the road, then VH1 has you covered. Season six of Love & Hip Hop: Hollywood airs on Monday, August 5 at 8/7c and will feature behind the scenes moments from the Millennium Tour that you won’t want to miss. In the meantime, check out the trailer below:

This is branded content, produced by our marketing department in partnership with our advertisers—not by editorial.


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