A photo grid of Remy Ma, Datwon Thomas, Rob Markman, and Carl Chery with the title “40 Over 40”.
LEVEL’s 40 Over 40 panelists (clockwise from top left): Remy Ma, Datwon Thomas, Rob Markman, Carl Chery, Brian “B. Dot” Miller

40 Over 40

Revenge of the 40-Year-Old Rapper: A Roundtable Discussion

Five people. Countless opinions. Let’s get into it.

Published in
28 min readJul 28, 2020

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Update 6/7/22: Level has a new home. You can read this article and other new articles by visiting LEVELMAN.com.

The last decade gave way to an interesting paradigm shift in hip-hop: Storied artists are transcending generational gaps, building careers that don’t necessarily flame out with age. You could blame it on the culture putting some miles on its odometer, with its most central figures in the driver’s seat and aging fans riding shotgun. Or perhaps it’s social media and the streaming era that have allowed artists to take control of their careers. Whatever the reason, artists who might conventionally be considered washed are dropping some of the dopest music out, their personal growth reflected in their raps.

This has all been the basis of LEVEL’s inaugural 40 Over 40 package paying homage to the rappers who continue to flourish. We did the work of highlighting and ranking the artists who’ve had the strongest post-40 runs in rap, but why stop there? To take things a step further, we assembled an all-star squad of music industry vets to discuss the modern landscape of rap’s elder statespeople — journalists, podcasters, artists, and executives.

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