This Rapper Just Broke the Record for the World’s Longest Freestyle — and He Did It All for Charity

And he intends to keep going until he hits 33 hours and 30 minutes. Photo: YouTube

San Francisco rapper, producer, and poet George Watsky just made history for a good cause, livestreaming a run to break the Guinness World Record for the longest continuous freestyle rap and raise money for his tour and crew, who were sidelined during the tour for his new album Placement as venues across the country shuttered to curtail the spread of COVID-19. Proceeds will also go to the Sweet Relief Musicians Fund, a nonprofit charity founded by singer-songwriter Victoria Williams in 1994 when multiple sclerosis left her unable to tour to pay her bills. Watksy has been rapping since Wednesday morning and, as of Thursday afternoon, beat the standing Guinness “Longest Continuous Rap Performance” record of 25 hours and 56 minutes, set by Pablo Alvarez of the band Good Bison in 2017, and he intends to keep going until he hits 33 hours and 30 minutes. Hip-hop heads very online in the blog rap era might remember Philly rapper Chiddy taking the crown with a nine-hour rap at the first edition of MTV’s short-lived O Music Awards in 2011. It’s gotten more competitive since then.

Over 24 hours in, Watsky’s run has been an absurdist stream of consciousness aided by coffee-table books, a Scrabble dictionary, and a list of fans to shoutout. He sounds shockingly lucid for someone who has been awake and talking for a day straight, but it’s dead weird watching someone empty the contents of their brain in real-time for that long, wondering out loud how to pronounce the sound that a motorboat makes, detailing the virtues of ChapStick, and rating his own butt on a 100-point scale. He can’t take long breaks, so periodically you catch him trying to rap between sips of water and fruit smoothies, or rhyming about peeing on mic but off camera from the bathroom. The big challenge comes from the shoutouts, offered as an incentive for donating $10. Watching Watsky try to find a word that rhymes with “Doinkle” — and succeed — was a trip. The show goes on until later on tonight, assuming he goes the distance, but it’s a win already: he’s already raised over $100,000 on Twitch.

Watsky Breaks the Record for the World’s Longest Freestyle