Why Do Nice Guys Always Finish Last In Hip-Hop?

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Chance The Rapper may be a better sport than he once was, but even the artist best known for his relentlessly cheery outlook and nonstop philanthropy has limits. The Chicago rapper lamented the lukewarm reception of his latest project, The Big Day, on Twitter, saying it felt like commenters wanted him to feel ashamed of something he himself was proud of — his gushing love for his wife and the accoutrements of married life.

While it’s true that Chance’s complaints carry a whiff of self-righteousness, he does have a point. Much of the criticism leveled against him online directly calls back to Chance’s music on Acid Rap — music he made at a much more tumultuous point in his personal history. “Get back on drugs,” many of the tweets say, insinuating that Chance’s music was better when he was miserable — and, troublingly, in danger of overdose.

Aside from being a generally gross attitude to have — many of these same accounts contain tweets from just a year ago mourning Mac Miller — such online reactions reflect an uncomfortable and long-held truth about rap and its fans: Hip-hop loves the bad guy. Our favorite rappers are at best assholes. At worst, they’re flat-out criminals. Both fans and critics have pointed out the detrimental effects positioning such characters as role models can have on rap’s impressionable fan base, yet when more positive examples come along, they are derided as corny. What gives? Why do nice guys always finish last when in hip-hop?

The question isn’t necessarily new, extending all the way back to rap’s foundational hits. Will Smith, as the Fresh Prince, was often scoffed at for being “squeaky clean” and making music that, contrary to the title of one of his biggest early hits, parents could understand — and approve of. Kid ‘N’ Play, Kriss Kross, Kwame and his “f*cking polka dots” — shoutout to Biggie — all caught hell in the early days of hip-hop. Even RZA famously had to switch his style up from “Ooh, We Love You, Rakeem,” to become the Wu-Tang overlord we all know and love today — not to mention his Gravediggaz experiment, which seemed calculated to further distance him from the “missteps” of his more colorful past.

The trend continues today: Amine, Big Sean, Chance, Childish Gambino, Kyle, Logic, and even Drake, to a certain degree, all face ridicule for being “too nice.” Even those rappers who seemingly turned their lives around after early rebellion saw a downturn in their critical and commercial reception. Eminem, Gucci Mane, and T.I. all received negative reviews from listeners and critics — Gucci on this very site — after kicking drug habits or giving up criminal activities for the betterment of their lives and continued career prospects. In light of those declines, Future’s fears about revealing his sobriety actually seem well-founded.

Why wouldn’t he — or any artist interested in maintaining a certain level of pop culture appeal — want to embrace the appearance of scumbaggery, when Chris Brown, renowned and unapologetic alleged abuser of women, currently holds a No. 6 position on the Billboard 200 and is currently No. 3 on the R&B/Hip-Hop Airplay chart with his new single “No Guidance?” Why wouldn’t family men like 2 Chainz and 21 Savage want to maintain an air of casual misogyny and leering, ghoulish menace, even though it’s clearly far from the actual lifestyles both actually currently maintain? Rapping about drugs — whether selling them or taking them — always seems to play better than rapping about your kids. “I got bitches” is a fan favorite refrain. “I love my wife” isn’t.

Even the most lovable of stars have to play into this dichotomy to a degree. Kanye rapped openly about his middle-class upbringing and the pitfalls of higher education. He also acts like a petulant child when he feels it suits him and pals around with openly racist politicians. Say what you want about the reception of his Wyoming Sessions albums, Kanye’s popularity barely took a hit from his MAGA-fueled rants; even his staunchest critics still show up to Sunday Service like clockwork.

Likewise, Drake may as well be the poster child for mawkish gentility but he’s half the reason “No Guidance” holds the chart position it does. That his “groundbreaking” partnership with his onetime rival basically comes despite — or perhaps at the expense of — their shared paramour. After all of Drake’s simpish, dramatized, displays of affection for Rihanna, as it happens, he’s still willing to dance with the devil and the audience is all too happy to play along. Drake plays a manipulative jerk on plenty of his records — it’s the ones where he comes across “way too earnest” that put listeners off.

Even in censuring Jermaine Dupri’s recent comments about female rappers, Cardi B pointed out that thoughtful, emotive content in her own catalog — and in those of other female rappers — was overlooked for the baser instincts of bars about sex and money. It seems that since the days when Jay-Z fronted as a mafia don, The Notorious BIG exaggerated his own dire conditions, and Tupac transformed himself from a classically trained dancer and poet into a “thug life” advocate, rap fans have embraced the hyperbolic fantasy of being exactly the kind of person you’d cross the street to avoid over anything resembling uplift and joy. Contrary to popular belief, “keeping it real” doesn’t actually play well in hip-hop.

It’s not all bad, though. Although Chance may notice the jokes more than the praise, a No. 2 debut on the Billboard 200 is nothing to knock (and that’s not to mention the rapper that kept him from No. 1, NF, whose labeling of Christian rap might make him the ultimate nice guy, but that’s another article entirely). The artists who’ve come up alongside him relating their own messages of optimism and sobriety are all well-known, commercially successful, and have found their own niches of fans to whom they appeal. Universal acclaim may be way out of reach, but they can each afford to continue pursuing their rap dreams their own way, assured that the music is reaching exactly the fans who need it most. BIG may have ripped Kwame for his fashion, but it seemed someone out there didn’t mind; “The Rhythm” was a US Hot Rap No. 1 for a reason. The people may joke, but that just means they’re paying attention.

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