Avoiding Obscurity: Rappers Who Never Stopped Improving


By Charles Holmes

The stereotypical trajectory of a rap career favors the young. Rappers seemingly explode on to the scene, becoming the genre’s prince before fading into relative obscurity. On average, rappers get a five-year span to make the most of the spotlight, either etching their name in history or being relegated to the doldrums of rap purgatory (e.g. relevancy thirst traps like Love & Hip-Hop).

However, this phenomenon is changing. As rappers continue to leverage the Internet to their advantage, many are getting a second chance. The internet has provided rappers instant access to fan support and criticism. This has allowed artists to radically change the course of their career by having their finger on the pulse. Thus old rappers are learning to become more malleable to the sounds of the time, while already successful rappers are extending their shelf life. In honor of this, here are the rappers that never stopped improving, and have well and truly avoided the trap of mid-to late-career mediocrity.

Click to start the list

  • P.eZ (R.I.P Ke’son)

    In just under 3 weeks since starting this page, with no label or anything I’ve managed to draw nearly 1,200 listens, with plenty of rave reviews…


  • annie non

    you, dear writer, are a fucking douche

  • jo

    list is mostly bull shit

  • Justice Taylor


  • Long.Live.AESOP

    Where the goddamn fuck is Aes?

  • menigga

    This is the Stupidest fucking list I’ve ever seen. You sir or ma’am do not know a fucking thing about hip hop.

  • younghydrocodone


  • Mikeyc


  • TBNH1980

    You are a fucking idiot. Danny Brown, Big Boi , El P and Killer Mike are on the list and if that ain’t “Hip Hop” for you then sit the fuck down a gently place the dick you took out of your mouth back in….fuckin poser. Smdh

    Edit : Did I mention you are a fuckin idiot? Lol

  • Juney

    Please get a more informed and passionate writers on your staff.

  • Y’all slippin 25/8

    This is jus a list of who’s hot right now get tf off they dicks or y’all jus all dumb

  • Dynamite

    Where is pusha t or Andre

  • menigga

    I was referencing everything but Run The Jewels, Big Boi etc. Go on with your nonsense idiot shit, but I’m talking about the majority of the list you baby fucker.

  • datnigga

    Lol you just got clowened. I agree with menigga. This writer doesn’t know hip hop at all.

  • Charles Holmes

    That’s your opinion and I respect it, but obviously you didn’t get the point of the list. This wasn’t a comprehensive list of my favorite rappers. It’s about rappers that got better over time. So legends like Jay, Nas, Em or even rappers like Curren$y or whoever else people want to mention don’t count because there most critically acclaimed work is behind them.

  • AriHunnaGrande

    why isn’t dom kennedy on this list?

  • http://peachesandcaramel.tumblr.com mudzi mashamba

    Big Sean and 2 Chains shouldn’t be on here

  • Big John Feen

    It’s as if this article was written by a high school student that just graduated. I skimmed past most of the list because I was like “who the fuck cares about that fuck?!” Big Boo and Run the Jewels are the only legit rappers on this list. The rest are too young or just not relevant.

  • Big John Feen

    Big Boi*…fucking auto correct bullshit.

  • Dagoat Man

    “Danny Brown is now 33, almost a full decade older than most of his peers and still rapping circles around them” <– so true tho

  • Dave

    Over time usually means a long time like Big Boi – Not Danny Glover or Drake???
    If you want to shout out people who have aged with the years in a fine way – why no De La? Yeah they might leave 4/5 years between releases. But they literally piss on everyone in your list – for rhymes, for passion for invention everything!

  • ∆∆

    seriously though… wheres currensy? from his no limit / cash money days to stoned immaculate and even new jet city, the dude has always delivered something new and awesome while still giving us exactly what he came for.

  • Charles Holmes

    All these artists were chosen, because they were generally written off, hated, or deemed as irrelevant by the hip-hop community. People like Childish Gambino, Danny Brown, Drake, or 2 Chainz are on the list, because they took what “real hip-hop fans” derided them for and improved over the years.

    I didn’t include most legends, (i.e. De La, Q-Tip, any member of the Wu, etc.) because there catalogues are etched in stone or they reached their creative peak. It’s unrealistic to think someone like Nas will release an album better than Illmatic or that the new Wu album will be revered as much as 36.

  • Khoko

    2 Chains? The guy could never rap and he can’t now. That is the opposite of improving.

  • Frank Moolah

    Kanye, Big Boi, 2 Chainz, Killer Mike is it, everybody else aint even noteworthy

  • DAve

    Sorry, what?? De La are no where near a creative peak and if you had heard their last DAISY AGE mixtape or Spirit of the Wu you would know that.
    I never mentioned Nas or the Wu.
    Drake is still making the same mushy-love music as forever and chart success doesn’t equate to creative greatness – 2 Chainz is terrible. Simply terrible and if you are using him as a marker of creative success you need to get out more. And he is still widely derided – again don’t equate chart success with creative acumen.

    Danny Brown is great but he’s only 3 albums in so how can you talk about his evolution of an artist over time?
    Run the Jewels have made 1 so ditto

  • K

    Literally the worst thing on the internet all week good job P&P

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