How Meek Mill Went From Freestyling on Street Corners to Running Street Rap

It's been a slow climb for the Philadelphia rapper, but he's finally joining the ranks of the upper echelon.

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Complex Original

Image via Complex Original

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Hip-hop is competitive. It always has been and it always will be. But in an era where the constant social media discussion surrounding an artist’s music can often overwhelm the music itself, that competition has taken on increased importance.

It is into that environment that Meek Mill, the Philadelphia rapper who first burst into hip-hop’s collective conscious on the back of a motorbike in 2011, released his sophomore album, Dreams Worth More Than Money. The 14-track effort is not an opus, but it is an excellently solid album that serves as a career-defining moment for an artist who’s traveled a road littered with setbacks.

Although he grew into fame as an industry darling, Meek’s early career was built not off major cosigns but a deafening local buzz gained by freestyling his brains out in the streets of Philadelphia. He formed a group called the BloodHoundz with three local affiliates and released four mostly forgettable mixtapes. Years later, Meek reemerged and released a trio of tapes—The Real Me 1 and 2 and Flamerz—that showcased his now-trademarked style.

The reckless energy that defined young, messy-cornrowed, battle-rapping Meek is exactly what helped him win the support of the bigger names rappers need nowadays. First came T.I. and a Grand Hustle deal that fell apart in the wake of Meek’s fateful 2009 arrest. Post-jail Meek found himself the apple of another superstar’s eye. In 2010 Rick Ross polled Twitter about young Philly talent only to have his mentions besieged by fans championing Meek Mill. The partnership began soon after. With jail temporarily behind him, MMG by his side, and the same energy that won him fans in the streets of Philly winning over the non-initiated all over, Meek broke out in 2011.

A few years ago Meek reaching this level of success seemed a foregone conclusion. Tracks like “Ima Boss,” “Tupac Back,” and “House Party” showed special levels of talent, and Dreamchasers 1 and 2 not only packed hits but also a cohesive intensity that all but guaranteed the excellence of his debut album.

Now three years removed from Dreams and Nightmares, we can see his formal inauguration for what it was: a bust. Besides the historically epic intro (seriously where would society be without it?) what else from that album does anyone have in rotation? It was a failure to deliver on a massive scale.

Thus began a relative cooling period, one that culminated tragically in a five-month jail sentence for parole violation. To make the ruling even more painful, the sentence came down two months before the intended release date for his sophomore album.

The powers that be scrapped the album roll out, and the future looked bleak. Few rappers have come out of jail the same artist who went in. Just ask Wanye. Or DMX. Or Shyne. Or T.I. Or anyone but Gucci.

Songs like “Ice Cream Freestyle” and “B Boy” established that he still wielded the same skills and furiousness. To many the most notable recent development is his relationship with Nicki Minaj, a woman whose talent is surpassed only by her fame. Their relationship has put Meek in front of more new eyeballs than basically anything else could have.

Meek, both in his career and in his personal life, is now in a new place, and Dreams Worth More Than Money, like much good art, reflects the circumstance of its creator. Thus it’s fitting that this album doesn’t sound like any Meek Mill project before it.

Throughout his career, Meek Mill has been best when most urgent. On songs like “Lil Snupe” or “Dreams and Nightmares” it sounds like he is rapping for his life, like he’s Jason Statham in Crank and his heart will continue beating only as long as he raps like a mad man. That urgent intensity made complete sense. It reflected a lifetime’s worth of desperation, honed by battle rapping his way through Philadelphia and shaped by the antagonism of the American criminal justice system.

Intensity has long been his calling card, and although it is thankfully still present on this album it is importantly no longer the main attraction. 

Intensity has long been his calling card, and although it is thankfully still present on this album it is importantly no longer the main attraction. However, he still shines brightest when voicing desperation both past and present. Bars like “You ever wash out your drawers on the same water you shit?/Doing your push ups right on the floor where you piss?” are as strong as any he’s ever written.

He’s more comfortable now, both in his life and in his music, than ever before, and that allows him to try some things we’ve never heard from him. He’s added layers to his style, his rhymes now work more internally than ever, and he’s started to experiment. DWMTM features self-sung Auto-Tuned hooks, songs built off classic rock riffs, and, most importantly, multiple love songs dedicated to Nicki.

For one of the most stereotypically rough rappers in recent memory, buttery soft ballads “All Eyes on You” and “Bad for You” necessitate a double take.

Although these singles will receive their fair share of criticism, they are far from the shameless attempts at crossover successes they could’ve been. Instead, they show hints of growth. At times the growing pains are visible. “I'mma just give you a key to my heart/You'll be the first that I let in the door” is unabashedly corny. But there are moments that provide both an insider view on a very public relationship and endearing cuteness, like the “Hey Ma”-esque back-and-forth on “All Eyes on You.” 

For many, these two songs will be the only takeaways from this album. After all, the lead image to this story will feature Nicki not only because that will get clicks but because that relationship is a major part of and reason for his heightened ​status as a public figure.

Although the new territory that Dreams Worth More Than Money traverses is sometimes unforgiving to Meek, the entire effort—its familiar successes, its newfound strengths, and its failures—is an impressive step forward. It’s the culmination of Meek shedding weak criticisms of his one dimensionality and welcoming a level of superstardom both inside of rap and in the larger world of pop culture that eluded him until this moment.

In a recent interview, Meek publically claimed that he doesn’t listen to J. Cole or Kendrick Lamar because “they don’t inspire [him].” If this statement wasn’t just macho rapper man posturing then Meek should maybe rethink it. Cole and Kendrick are the most recent additions to hip-hop’s current chosen few, joining Nicki, Drake, and Kanye. If their music doesn’t inspire him, their recent ascension should. With this album, he’s come as close as anyone is to joining their ranks.

Meek Mill has long shown himself to be a man obsessed with dreaming. For the most part those aspirations have concerned achieving success in his field. He voices that on this album, saying, “Whoever thought lil' ol' Meek Milly'd pass Jigga?/I'm just thinkin' a tad bigger.” In dismissing whatever inspiration he may get from the artists who constitute his few challengers for preeminence, Meek is playing into the competitive spirit that has driven him since his SMACK battle days and long defined the art form he excels in. He now competes in a league many aspire toward but few ever reach, a newly minted superstar finally getting comfortable.

Max Goldberg is a writer living in New York. Follow him @goopygold.

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