From Struggle to Stardom: How Your Favorite Rappers Were Discovered

Time may be our most valuable currency in an era defined by immediacy. Here in 2014, we’re used to instant accessibility in our communications, transactions, and entertainment. It makes sense, then, that the rate at which relatively unknown artists skyrocket to success has seemed to accelerate in recent years; take Bobby Shmurda, who recently closed a deal with Epic Records off the strength of one catchy song and an even more addictive six-second Vine clip. It’s easy to forget that Shmurda’s speedy come-up is far from traditional, even by today’s standards. Even these guys will tell you that “I can make you a celebrity overnight” is a promise way easier said than done.

For most superstar rappers, the come-up involved corny day jobs, awkward name changes, forged and lost alliances, equal parts thirst and luck, and above all, years and years of hustle (not to mention patience). It’s bizarre to imagine a time when Nicki was Onika, snapping on her Red Lobster customers, or when Drake was Aubrey, nervous to set foot on Lil Wayne’s tour bus for the first time. However it’s a reminder that at one point, your favorite rapper wasn’t all that far off from the struggle MCs polluting your mentions. Confidential to struggle rappers: That tactic never works. Well, unless you’re Meek Mill.

The Queens-raised Harajuku Barbie, known then as simply Onika Maraj, was more invested in theater than music during her years at NYC’s arts-focused LaGuardia High School. But after a brief, unsuccessful stint in an Off-Broadway play, Nicki found herself in a string of unsatisfying jobs she could never hold down for too long.

“I’d been fired like 15 times because I had a horrible attitude," she told Billboard in 2010. "I worked at Red Lobster…and I chased a customer out of the restaurant once so I could stick my middle finger up at her and demand that she give me my pen back.”

She then joined a four-person rap group called the Hoodstars (along with Scaff Beezy, her rumored boyfriend to this day), but soon left to pursue a solo career—at this point, under the name Nicki Maraj.

Nicki’s break came when Fendi, CEO of Brooklyn label Dirty Money Entertainment, came across her MySpace. He signed her almost immediately, convincing her to change her name from Maraj to Minaj (“Just because I have a nasty flow, and I eat these bitches”). Fendi brought in Debra Antney (perhaps better known as Waka Flocka Flame’s mom) as her manager, and co-signed her on his Come Up street DVD series (Nicki appeared on Volume 11 in 2007, spitting venom and brandishing a stack). Lil Wayne saw her Come Up appearance and was instantly won over. That same year, she contributed a verse to Da Drought 3. Finally, in 2009, Young Money announced they’d officially signed Nicki, just a few months after her third (and best) mixtape, Beam Me Up Scotty, dropped.

By now, you’ve seen more than enough Wheelchair Jimmy memes to be intimately aware of Aubrey Drake Graham’s five-year gig on the Canadian drama Degrassi: The Next Generation. His rap career was well on its way by the time he left the show in 2009. He released his first mixtape, the aptly titled Room for Improvement, in 2006, and “Replacement Girl,” a collaboration with early ally Trey Songz from 2007’s Comeback Season tape, became the first track from an independent Canadian rapper to be featured on BET. Houston talent scout and CEO of Rap-a-Lot Records, Jas Prince, discovered Drake’s music—again on MySpace (those were the days)—and convinced Lil Wayne to listen. When Wayne finally obliged, he requested Drake be flown out to Houston a few days later. (Prince has since filed a lawsuit against Drake’s management team claiming an agreement to split profits between himself and then-manager Cortez Bryant was never honored.) All the same, Drake flew to Houston in 2008 to meet Wayne for the first time in his tour bus.

“Wayne was getting like the most painful tattoo in the world,” he recounted to Interview Magazine in 2011. “He was getting these huge wings on each side of his body.”

Wayne played him Tha Carter III, which had yet to be released, and Drake stayed on the road with him for a week and a half, during which they recorded “Ransom” and a remix to “Brand New.” Drake’s star-making mixtape So Far Gone dropped in 2009, and a few months later, he announced that he was signed to Young Money.

Though he’s not yet into his 20s, Chief Keef—born Keith Cozart—is no rookie in the rap game. At age 10, he was already freestyling over his family’s karaoke machine. (He and his friends called themselves Total Domination.) He, along with his cousin Fredo Santana, began recording around the year 2007, thanks to a chance meeting with DJ Kenn, a Japanese immigrant Keef’s uncle picked up wandering through their neighborhood. Kenn came to produce many of Keef’s early hits, including his first hit, 2011’s “Bang.” The track coincided with a period when YouTube was becoming an extremely effective medium for disseminating music among teens in Chicago’s public school system. The track racked up a million views even before anyone outside of his hometown knew his name.

As “Bang” picked up steam, Keef (then 16) was sentenced to a month of jail time for pulling a gun on police. The day he was released, a WorldstarHipHop video titled “It’s Something Wrong With This Lil Boy: Freaks Out When He Finds Out His Favorite Rapper ‘Chief Keef’ Gets Out Of Jail,” went viral, introducing many to Keef for the first time. In early 2012, Keef got some high-profile co-signs when Lil B and Soulja Boy remixed two of his songs. Though, his most star-powered assist came when none other than Kanye West remixed his bubbling single “I Don’t Like.” A month later, Keef announced his deal with Interscope, as well as a publishing deal with Dr. Dre for special edition Beats by Keef headphones.

Raised in Atlanta (though born in Haiti), the artist born Nayvadius Wilburn had a bit of an advantage from the jump. His cousin was Rico Wade, founding member of the Organized Noize and Dungeon Family crews, who encouraged him to focus on songwriting in order to stay out of trouble. As a result, Future joined Da Connect, a group comprising second-generation Dungeon Family members; they released an album to little fanfare in 2003. Meanwhile, he honed his production skills alongside Wade, landing a songwriting credit on Ludacris’ “Blueberry Yum Yum” in 2004. At the time, he went by the name Meathead the Phuture—yes, with a “P.”

Eventually, fellow ATLien Rocko (of “U.O.E.N.O.” fame) signed him to his A-1 Recordings label, and—fortunately for us all—convinced him to simplify his name to Future. Rocko was well acquainted with L.A. Reid; he’d signed to Def Jam briefly in 2007, though it didn’t end up panning out. After a strong 2010-11 for Future, during which he pumped out a series of increasingly popular mixtapes (1000, Dirty Sprite, True Story, and his Free Bricks collaborative project with Gucci Mane, not to mention a scene-stealing hook on YC’s propulsive single “Racks”), Rocko ultimately led Future in Reid’s direction. Now the CEO of Epic Records, Reid signed Future in 2011—20 years after he’d signed his uncle Wade to Def Jam. Voila, magic.

At age 16, Iggy Azalea (then Amethyst Kelly, raised in the rural, 3,000-person Australian town of Mullumbimby) told her parents she was headed on vacation and booked it to Miami with no plans of returning home. After brief stints in Miami and Houston, Azalea made herself at home in Atlanta, where she befriended Backbone of the Dungeon Family and Big Oomp and DJ Unk of Big Oomp Records. Though she was used to getting laughed at for pursuing a rap career, her connections helped hone her skills and let her record in their studio spaces.

In 2010, Azalea moved to L.A., where she and a friend ran a hair company so that she could get her green card. In 2011, she emptied her bank account to record the video for “Pu$$y,” the single from her first mixtape, Ignorant Art. The super-sexy, super-catchy video went viral shortly thereafter. It caught the attention of T.I., who signed Azalea to his Grand Hustle label in 2012. Around the same time, she became the first woman included on XXL’s annual Freshman Class cover.

It’s possible that Meek Mill was simply destined to end up in the Maybach Music roster—that the Philadelphia rapper was born Robert Williams, whereas Rick Ross’ given name is William Roberts, is almost too weird to be a coincidence. Not quite, though: Meek worked his way up, starting as a member of four-man group the Bloodhoundz from 2003 to 2007. But he struck off solo in 2008, launching his Flamers mixtape series. “In My Bag,” off his first Flamers tape, became a favorite in Philly clubs and radio stations. That momentum garnered some local co-signs, including Young Chris and Cassidy, and ultimately caught the attention of T.I. Meek was in talks of signing to his Grand Hustle label, but that plan fell apart when he was arrested. He was released in 2009. A year later, he released Flamers 3 as part of DJ Drama’s popular Gangsta Grillz mixtape series.

His break came shortly thereafter: Rick Ross, passing through Philly, had asked his Twitter followers what local rapper he should work with while in town. Meek was the overwhelming response, so Ross extended an invitation to the radio station he was visiting. “The homie had those matted-up braids at the time,” Ross joked during his CRWN interview with Elliott Wilson earlier this year. “Looked like my dog ain’t have his shit done in five months.” Even so, Ross jumped on the remix of Meek’s “Rosé Red” single later that year, and in 2011, he officially signed to MMG. His singles “Tupac Back” and “Ima Boss” dropped soon after.

In his high school days, Detroit native Big Sean (born Sean Michael Anderson) often took part in weekly rap battles held by a local radio station. Sean was working as a telemarketer during the summer between his junior and senior years, making $100 a week. While in the middle of cashing his meager check one weekend, a friend alerted him that Kanye was being interviewed at another local radio station. Sean booked it across town, using his radio connections to get inside the station.

“Kanye shook my hand and started walking away,” Sean recounted to MTV in 2009. “I tapped him on the shoulder and was like, ‘I’m an aspiring emcee. I do this show every Friday. Can I rap for you?’ He was like, ‘No. I gotta go.’ I’m like, ‘Man, please—you’re my hero… Just let me spit for you.’”

Kanye caved and gave him 16 bars, which turned into 10 minutes as 'Ye bobbed his head in approval. Though they lost touch for a bit, 'Ye ultimately brought Sean on the road while he recorded Graduation. Sean had planned to attend Michigan State after his own graduation (he’d finished high school with a 3.7 GPA). Instead, he signed to G.O.O.D. Music in 2007.

Jermaine Cole, born and raised in Fayetteville, N.C., began rapping at age 12. By 15, having run out of friends who’d make beats for him, he was teaching himself to make them. Based on his starry-eyed conception of New York as an underground rap mecca where the ciphers never end, he attended St. John’s University after high school, where he focused even harder on a new side of the grind: networking.

“I tried everything, dog,” he told Complex in 2009. “I mean MySpace message, making up shirts with slogans like ‘Produce for Jay-Z or Die Trying.’” In 2007, Cole posted outside of Jay’s Roc the Mic studio with a CD full of beats. When Jay arrived, he immediately shut Cole down, scoffing “Man, I don’t want that.”

“I thought he was evil at that point,” Cole admitted to ABC News.

But in late 2008, after graduating, he returned from playing a college show in L.A.—one of the few he’d actually gotten paid for, at that point—to the news from a friend that he’d arranged a last-minute meeting with Jay, prompting Cole to walk straight out of his day job. At the meeting, he impressed Jay with “Lights Please,” a track that would ultimately end up on his sophomore mixtape, The Warm Up. Three weeks later, Cole became the first artist signed to Jay’s newly founded Roc Nation imprint.

Born Scott Mescudi in Cleveland, the future “man on the moon” was expelled from high school for threatening to punch his principal (though he eventually earned his GED, and briefly studied film at the University of Toledo). In 2004, Cudi left Cleveland to live with his uncle in the South Bronx. After repeatedly getting turned down, he finally landed a job working at the newly opened NYC BAPE store.

“I remember Kanye coming in one time and I was helping him get a couple things,” he told Hypebeast in 2009. “I forgot to take a sensor off one of the jackets he bought, and I had to run out the store to catch him before he left. Pretty funny me chasing after him in Soho.”

Cudi didn’t introduce himself then, but years later, his manager Plain Pat passed his first mixtape, A Kid Named Cudi, in Kanye’s direction. Intrigued, ’Ye showed up at the tape’s release party in July 2008. That same summer, ’Ye enlisted Cudi to help write hooks for The Blueprint 3. Cudi then co-wrote a solid handful of tracks for 808s & Heartbreak, including “Heartless,” “Welcome to Heartbreak,” “Paranoid,” and “Robocop.” After a whirlwind summer, Cudi signed to G.O.O.D. Music that fall.

Compton-born and raised, Kendrick Lamar released his first mixtape, Youngest Head Nigga in Charge, at age 16, while still under his original moniker, K-Dot. Off the strength of that tape, he wrangled a recording contract with Top Dawg Entertainment, a new indie label out of Carson, Cali. During 2005 and 2006, Kendrick and fellow TDE member Jay Rock opened for the Game’s tour. As K-Dot, he was featured on Game tracks “The Cypha” and “Cali Niggaz.”

He received a crucial co-sign from Lil Wayne in 2009, leading him to call his next mixtape C4 as an homage to Wayne (the tape opened with audio of the co-sign). That same year, he dropped K-Dot in favor of his real name, and formed his Black Hippy crew along with Jay Rock, ScHoolboy Q, and Ab-Soul. After spending 2010 touring with Tech N9ne, Kendrick dropped his fourth mixtape, Overly Dedicated, through TDE. The tape found its way onto the Billboard hip-hop charts, peaking at 72. One of its tracks, “Ignorance Is Bliss,” caught the attention of Dr. Dre, who reached out and recruited Kendrick to work on Detox—yep, that album’s release was still in the realm of possibility—along with he and Snoop. After a massive 2011, during which Kendrick landed the XXL Freshman Class cover and released his star-making Section.80 mixtape, Kendrick and the rest of TDE closed a joint venture deal in 2012 with Interscope and Dre’s Aftermath Entertainment.