Rap’s Most Impressive Career Evolutions Of The Decade

In the 2010s, the code was cracked for “grown man rap.” Veteran acts like Jay-Z, Black Thought, Little Brother, and others proved that rappers could age gracefully in the game. There were also plenty of artists like Danny Brown, Benny The Butcher, and Freddie Gibbs who broke through in their 30s. This list is a testament to those underdog, the come-from-behind acts.

It seems like everyone has been doing the 2009/2019 challenge on social media, which made me want to salute the artists who have made the biggest evolution in their careers from 2009. But there’s a specific criterion for this list. It won’t consist of pre-2010 XXL Freshman or other artists who had already broken through by 2009. It was fairly easy to predict that heavily-affiliated artists like Drake, Nicki Minaj, J. Cole, and Big Sean were on their way to some form of success in the 2010s.

This list is about artists who were in the industry but weren’t minted for solo rap stardom in 2009:


Brownsville Ka has had the longest road to success of any artist on this list. Ka had been rapping since the ‘90s as a member of the Nightbreed duo. He finally received a break when he appeared on GZA’s 2008 Pro Tools album. He released his debut Iron Works project that same year, and has since established himself as one of the underground’s most respected voices — while juggling a career as a New York City firefighter.

In 2019, at 47, Ka is still going strong and has no intention to stop adding to his catalog of heartfelt, introspective albums. His career exemplifies that it’s never too late for someone who believes in themselves and their craft.

French Montana

A decade ago, French Montana was arguably more known as the host of the Cocaine City street DVD series than as a rapper. In 2009, French ended up releasing the memorable Coke Wave mixtape with Max B, a cult hero who French befriended due to mutual beef with Dipset’s Jim Jones.

French sounds raw on the project, but he steadily developed his rap skills on collaborations with Max and his own mixtapes. French signed with Akon’s Konvict music label in 2009, but that deal quickly dissolved. When Max was convicted of murder and sentenced to 75-years (a term which has since been drastically shortened), French signed to Atlanta-based management Mizay entertainment and began affiliating with other artists such as Waka Flocka, Gucci Mane, and Rick Ross. He eventually signed to Bad Boy in 2012, and has since ascended to a level of fame that few had foreseen for him.

Benny The Butcher

Benny The Butcher was known as B.E.N.N.Y. in 2009. In April of that year, the Buffalo rapper released his second mixtape entitled Chains Bond. His burgeoning lyrical ability was apparent on the mixtape, but it was hard for him to gain traction as a Buffalo-based MC. By 2014, his cousins Westside Gunn and Conway founded Griselda Records and began rapping.

By then, B.E.N.N.Y. was going by Benny The Butcher. He gradually became an integral part of the movement’s prolific output through his Tana Talk series and other projects. 2019 was Benny’s biggest year yet. His Plugs I Met album was one of the year’s most critically acclaimed projects and he signed a management deal with Roc Nation.

Danny Brown

In 2009, Danny Brown was a fledgling Detroit rapper trying to breakthrough. He had a brush with the industry years before when then-Roc-A-Fella A&R Travis Cummings flew him to New York to work with the label, but eventually, he ended up back in Detroit. With no career prospects, he began selling drugs and ended up doing eight months in jail. After coming home, he rededicated himself to music.

By 2010, he began working with Tony Yayo of G-Unit. The two put together a mixtape entitled Hawaiian Snow. Danny recalls that G-Unit boss 50 Cent liked his music — but didn’t like his tight clothes and wild hair, and passed on signing him. Undeterred, Brown further honed his craft, specifically the animated delivery that would eventually see him sign to Fool’s Gold Records and release the breakthrough XXX album.

Ten years later, Danny has built a strong career as one of the rap game’s most unique personalities. He has released four albums in the decade, most recently U Know What I’m Sayin?, which Q-Tip executive produced.


Big KRIT released his sixth mixtape entitled The Last King in 2009. The then-aspirant from Mississippi then made noteworthy appearances on Wiz Khalifa’s Kush & Orange Juice classic in 2010, which paved the way for his breakthrough K.R.I.T. Wuz Here mixtape. He signed to Def Jam Records in 2010, and became a 2011 XXL Freshman.

KRIT has since left Def Jam and crafted one of the best discographies of the 2010s. Even while dealing with label woes, he’s one of the few artists who released a project every year of the decade.

Freddie Gibbs

In 2009, Freddie Gibbs released The Miseducation of Freddie Gibbs, a mixtape compilation of his work from 2006 until then. The Gary, Indiana rapper was signed to Interscope in 2006 but didn’t get to release any music through the label. Gibbs began releasing a slew of mixtapes from that point, eventually signing — and falling out with — Jeezy’s CTE Records. In 2012 he left CTE and embarked on an independent journey.

In 2019, Gibbs proclaimed himself the “best rapper alive,” and there are many who agree with his assertion. His work with Madlib has resulted in two of the decade’s best rap albums with 2014’s Cocaine Pinata and 2019’s Bandana. The latter was written while he spent three months in an Austrian prison after being charged with sexual assault. The cases were dismissed in September 2016. Since resolving, he’s continued his rap career and developed the kind of catalog few people saw coming in 2009.

Roc Marciano

In 2009, Roc Marciano was a talented but unheralded artist trying to make sense of the music industry. He was a member of Busta Rhymes’ Flip Mode Squad, but left the crew in 2001. After winding journey including a feature on a Wu-Tang compilation album and a sting on Carson Daly’s (yes, that Carson Daly) 456 Entertainment, Roc decided it made the most sense to go about his career on his own terms.

2010 saw the release of Marcberg, a landmark album that made an immense impact in the rap underground. In 2019, Marciano is a self-made giant who helped pave the way for abstract, flashy rhymers like Westside Gunn and Action Bronson. He was one of the first artists to craft and rap over loops with light (or no) drums, which has since become an underground standard. Roc was one of the few people on the list who made a career for himself on his own terms — and kept it that way.

ASAP Rocky

The ASAP Mob hadn’t made their bones by 2009. ASAP Yams, ASAP Bari, and ASAP Illz had cultivated a collective of artists of all disciplines, and Rocky was a standout of the crew as a rapper. The mob was building their name in New York’s closely-knit fashion and music scenes. Yams had an eclectic musical taste, and sought to help Rocky breakthrough with a sound that eschewed regional boundaries.

2011’s “Purple Swag” was a polarizing moment for rap fans — specifically New Yorkers — unaccustomed to seeing a Harlem rapper lean so heavily into Houston rap culture. But the Mob’s visibility continued to grow online and otherwise, eventually leading to a $3 million deal with RCA Records. In 2019, Rocky is solidified as one of his era’s iconic acts. His 2019 started off rough with a stint in Swedish jail after an altercation, but he’s since resolved the charges.

2 Chainz

2 Chainz deserves an award for best rap rebrand ever. In 2009, he was Tity Boi, a member of the Playaz Circle duo signed to Ludacris’ Disturbin Tha Peace Records. Playaz Circle was known for “Duffle Bag Boy” with Lil Wayne, but little else. By 2010, Tity Boi left DTP and embarked on a solo career.

In 2011, he changed his name to the more palatable 2 Chainz, and dropped T.R.U. REALigion. From there, he has crafted one of hip-hop’s best 2010s catalogs with albums like Rap Or Go To The League.

In 2009, he was signed to an artist who was considered a candidate for Atlanta rap’s Mt. Rushmore. But now, in 2019, he has a claim all his own.

Pusha T

Pusha may seem like a strange addition to the list because his Clipse catalog had already solidified him in hip-hop’s annals. But his solo career is an entirely different chapter. After meager sales of Clipse’s 2009 Til The Casket Drops album, and the 32-year sentence their manager Anthony “Geezy” Gonzalez received for drug trafficking, the duo took a break. The future was uncertain for both artists.

Malice turned to Christianity and became No Malice, while Pusha signed with GOOD Music in September 2010. He released Fear Of God in 2011 and never looked back. Pusha not only proved that he could carry a project on his own, but he also became one of the best rappers of the decade with projects like My Name Is My Name and 2018’s instant classic Daytona.

Kendrick Lamar

It may seem hard to believe, but there was a time when Kendrick Lamar wasn’t regarded as a king of rap. In 2009, he and his TDE comrades were just another crew of rappers trying to put on for L.A., a city that hadn’t boasted many commercially successful acts during the aughts.

Many of the peers that Kendrick would eventually be compared to (and infamously call out on 2014’s “Control”) were already on the fast track to stardom, but the newly-formed Black Hippy collective of Kendrick, Jay Rock, Schoolboy Q, and Ab-Soul were still grinding and making a name for themselves. At the time, Jay Rock was the most well-known artist off the strength of his 2008 “All My Life” single. In 2010, Kendrick released Overly Dedicated, which got the attention of Dr. Dre and garnered him XXL Freshman status in 2011

And you’d pretty much have to be living under a rock to not know where the story goes from there. In 2019, Kendrick is already a bonafide hip-hop legend, with an arguably flawless solo catalog and hip-hop’s first Pulitzer Prize. In 2009, he released a mixtape called C4. Maybe it was a self-fulfilling prophecy because he blew up and then some.

Some artists covered here are Warner Music artists. Uproxx is an independent subsidiary of Warner Music Group.