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.