Hip-hop has never been about following rules. From the genre’s birth in the late ‘70s to today’s explosion of innovative pop-rap superstars, the music has always rewarded audacious creativity and outside-the-box thinking. While hip-hop has gone mainstream and become the world’s preeminent form of popular music, there are still artists working outside of industry boundaries and refusing to let labels, managers, or anyone influence their art. Below, we give props to five uncompromising artists who’ve found their own lanes and chased greatness on their own terms.
Dessa: A Multifaceted Artist with a Singular Voice
Before launching her career as a rapper, singer, spoken-word artist, author, and Doomtree label head, the Minneapolis native born Margaret Wander worked as a technical writer for a medical company. In a sense, she’s come full-circle with Chime, the critically acclaimed album she released in early 2018. It’s Dessa’s fourth collection of smart, soulful alternative hip-hop songs, and it was inspired by a project whereby she collaborated with neuroscientists to pinpoint the exact part of her brain dedicated to romantic love. Chime is just the latest example of how this one-time philosophy major has challenged the idea of what a female hip-hop artist can be. In a 2018 interview with Billboard, Dessa shared her secret for having such a rich and varied career: “I worry a little bit less about trying to forestall people’s opinions and just try to do good work.”
Cardi B: A Personality Too Big to Fail
By the time Cardi B topped the Billboard Hot 100 in 2017 with “Bodak Yellow,” the Bronx native was already on her fourth career. In the years leading up to her musical breakthrough, Cardi went from stripping to making viral videos to stealing scenes on Vh1’s Love & Hip Hop: New York. All of those pursuits showcased the qualities that would make Cardi one of the most exciting new rappers of the ‘10s. Cardi is sexy and funny, outrageous and vulnerable, tough as hell yet instantly loveable. Her excellent 2018 debut album, Invasion of Privacy, reached #1 on the Billboard 200 and silenced critics who thought she’d be a one-hit wonder. Invasion of Privacy has spawned a second chart-topper, the Latin-flavored “I Like It,” which you’ve surely heard blasting from cars all summer. While pregnancy kept Cardi from touring in recent months, motherhood is only going to make this vivacious truth-spitter a more compelling artist in years to come.
Tyler The Creator: More Than Just a Troublemaker
When the Odd Future collective came on the scene in 2010, nobody knew what to make of them. The blog-hyped L.A. rappers became infamous for their offensive lyrics, chaotic life shows, and unwillingness to play by anyone’s rules. Leading the pack was Tyler The Creator, a multifaceted troublemaker who’d spend the next decade revealing his genius. In addition to overseeing numerous Odd Future releases and four solo LPs — including last year’s Grammy-nominated Flower Boy — Tyler has directed music videos, launched his own Golf Wang clothing line, and spearheaded the Camp Flog Gnaw Carnival music festival. Tyler’s extracurriculars make it easy to overlook his rapping, but the fact is that he’s a stellar MC with the power to make you feel all sorts of ways. On Flower Boy, Tyler surprised everyone by serving up his most mature, confessional lyrics to date. Tyler sums up his career perfectly on the song “Who Dat Boy,” asking, “Who dat boy? Who him is?” The world will be chewing on those questions for quite a while.
Curren$y: The Underground Hero Who Never Lets You Down
The New Orleans rapper born Shante Scott Franklin knows how the big boys operate. He signed with Master P’s No Limit label in 2002, then struck a deal with Lil Wayne’s Cash Money Records in 2004. Curren$y appeared on Weezy’s Tha Carter II in 2005 and dropped the minor hit “Where Da Cash At” the following year. Neither of those projects quite made him a star, so in 2007, Curren$y jumped ship to the independent digital-only Amalgam Records and rebranded himself as a niche underground artist with an ear for consistency. In 2011, Curren$y, a.k.a. Spitta, formed Jet Life, the label he’s used to launch some of his many, many, many projects. Free of major-label interference, Curren$y has amassed a massive discography that includes eight studio albums and more than 40 mixtapes. More importantly, he’s built a devoted fan base that comes to see him perform live year after year. Spitta’s not going to break streaming records like Drake, but he’s a dependable artist in an age of disposability.
Chance the Rapper: The Superstar Who Gives His Music Away
When Chance the Rapper picked up the Grammy for Best Rap Album in 2017, it was notable for two reasons. First off, Chance’s Coloring Book is an incredible collection of gospel-inflected hip-hop songs from an artist who speaks on social issues without getting preachy or forgetting that music is supposed to be fun. Second, Coloring Bookwas the first-ever streaming-only album nominated for a Grammy. While the Recording Academy didn’t change its eligibility rules specifically for Chance, the Chicago rapper had long been at the forefront of artists challenging traditional release models. Chance is the king of the free “mixtape” — that’s how he classified Coloring Book and its predecessors Acid Rap (2013) and 10 Day (2012). Fans were able to get their hands on all three totally free of charge, and that’s helped Chance grow a gigantic fan base that includes Barack Obama, who praised the MC in 2017 for “representing the kind of young people who come out of Chicago and change the world.” Although he’s avoided selling his music, Chance has earned so much money off touring and merchandise that he was able to donate $1 million to Chicago schools.
In 2015, 
