Did Tyler, the Creator Just Deliver the Gayest Freestyle in Rap History?

by Lester Fabian Brathwaite

5h ago

Hip hop may still be homophobic, but with Lil Nas X breaking the record for the longest-running No. 1 single in Billboard history this week, rap’s got some gay assless chaps to kiss. Now critical darling Tyler, the Creator has scored another win for Team Queer with a fire freestyle in which he flirts with New York D.J. Funkmaster Flex.

Tyler recently dropped by the radio station Hot 97 to chat with Flex, who asked the rapper to get creative with a little off-the-cuff number. Little did Flex know what he was getting himself into.

Halfway through the performance, the 28-year-old MC raps about having a date with some dude to get ice cream. His date, however, canceled, so he is forced to find someone else. “What you use? Tinder, Gindr, get with all your niggas and get right behind him?” Tyler spits to a visibly amused Flex.

By the time Tyler starts to elaborate on some romantic scenarios featuring him and Flex—”cuddled up watching Scooby-Doo eating Scooby Snacks”—it’s clear we’ve wandered into some stunningly awkward but compelling territory.

In the past, Tyler has been coy but not quiet about his sexuality, teasing a relationship with fellow quirky millennial Jaden Smith, bragging about “kissing white boys since 2004” on 2017’s Flower Boy, and urging actor and universal bae Timothée Chalamet to “come get at me.”

Tyler’s latest album Igor, detailing a breakup with a man and its aftermath, debuted at No. 1 earlier this year to rave reviews. Vulture praised the album for containing “some of the most refreshing verses about same-sex attraction in a major label hip-hop field of play since Frank Ocean switched pronouns on the love interests he was singing to, and Kevin Abstract, Young M.A, and iLoveMakonnen spoke their truths.”

While it’s great that hip hop has a new queer hero in Lil Nas X, with this freestyle Tyler, the Creator reminds us we may have had one all along. And he’s fucking hilarious.