Funkmaster Flex Night: How a Letterman Diss Became Hip-Hop Legend

By 1992, Flex was not only getting paid at the Palladium, his sets at the club were being broadcast live on Hot 97, the radio station where he’d be working on the night that his name reached CBS. “I think it was the program director who said, ‘Oh, they talked about you on Letterman,'” he recalls. “That didn’t really register.” This would have been the end of it had a Hot 97 employee not tracked down a tape of the episode, then flipped Dave’s snark into a commanding call-to-arms. “The guy who did the promo was the real genius,” says Flex. “He played it and looped it to make it have that impact, make it sound like it was being scratched.”
The new drop made it onto the air within a week, and Perez heard it on night one. “Do you know those big, fact, chunky cell phones?” she asks. “My big, fat, chunky cell phone was ringing off the hook. I was driving in my Jeep, and it kept ringing and ringing and ringing.” Finally, she pulled to the side of the road — “I think it was Midtown; I have a vision of Seventh Avenue in the 50s” — and answered. “I’m what like, ‘What?’ And they’re like, ‘Yo, Funkmaster Flex bit your shit! He stole the drop from Letterman and he’s using it as his tag on the radio!'”
She kept the car in park and the radio tuned to 97.1 FM but soon gave up on waiting. “I started driving and then I heard, ‘Funkmaster Flex Night, Funkmaster Flex Night.’ I screamed! I went, ‘Ahh! That’s so dope! That’s so fly!’ And then I called my friends back, and they were like, ‘He didn’t give you credit!’ I was like, ‘What? Who cares!?’ It was awesome.”
Today, however, Flex puts it all on Rosie. “Letterman was snappin’ on me,” he says, “but for her to say it and for him to repeat it, it was a big deal. She was one of the few actresses, celebrities, that hip-hop wasn’t a stepping stone for. She was probably the only person at that time — I’m trying to think of who else — that would mention hip-hop, that wasn’t afraid.”
Whether or not she was afraid, the young star — who would soon earn an Oscar nomination for her work in Fearless — understood that she was taking chances. “People would always tell me, ‘Why do you have to play that music? Why do you always have to talk about hip-hop and rap? Why do you have to use that street vernacular? Why won’t you show people that you’re really smart?’ And I said, ‘Because I am really smart!’ I don’t owe anybody an explanation in regards to my intelligence. It was absurd to me, and I just didn’t want to play the game.”
Perez’s Letterman interview further proved her point, and Dave’s Funkmaster Flex shout-out — however mocking — brought insomniacs around the country a little bit closer to New York’s underground. “It just kept moving the wheel of the hip-hop movement forward,” she says. “How could I hate on that?”