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

The Late Show With David Letterman broadcasts its last episode on Wednesday night, but in New York City, the voice of the show’s host will remain on the air, emerging three words at a time from radios across the region. You can thank Funkmaster Flex. Six nights a week — he allows himself Sunday off — the 47-year-old DJ spins hip-hop on Hot 97 and often transitions between songs with a pair of instantly-recognizable effects: the sound of a bomb exploding and a sample of Letterman enunciating the name of his old party, “Funkmaster Flex Night.”

Flex has been cueing up this drop for 22 years, but he never gave much thought to its unusual staying power. “For some reason, it became a big deal,” he says. “I guess it was to some kids because Letterman is so not hip-hop. I was so hood…it was like, ‘When did he find time to say Flex’s name?!?'”

The story begins with a Page Six rumor: In fall of 1993, the New York Post falsely reported that Rosie Perez had been wed to a guy named Rocky. “Everybody was after me,” the actress remembers. “David Letterman made it a big joke about it — it was really great.” The conversation began with Letterman presenting the In Living Color choreographer a set of his-and-hers embroidered towels. “I was so flustered that day,” she says. “He would always take advantage of that — and rightfully so, because it made good television. You never knew what was gonna come out of the man’s mouth, so that was part of my nervousness, too.”

After the commercial break, Perez begins to talk about directing Lisette Melendez’s “Goody Goody” music video — and how she cast the lead heartthrob after spotting him at one of her favorite parties in the city. “It was really hard to find a guy from around the way,” she tells Letterman. “So I was going to the Palladium on Funkmaster Flex Night, you know that?” “Oh, yeah,” he responds, intentionally over-enunciating the name of the party. “Funk. Master. Flex night… Hard to get a ticket to Funkmaster Flex Night.” 

“David Letterman made fun of me,” Perez now recalls. “When I said, ‘Yeah!’ I wasn’t joking or playing dumb. I’m like, ‘Yeah, it is hard to get a ticket! He is that good! Everybody wants to get in there! You go and you’ll have to wait on the line.’ I didn’t have to wait on the line, thank goodness, but you know.”

For both Flex and hip-hop, this mainstream moment was one outcome from years of gate-crashing. The DJ had quickly become one of New York’s hottest, but even the Palladium, his biggest venue, initially turned him away. “The owners and the police said that they didn’t want me,” he remembers. “I went there for free one night, and I told them, ‘If you give me a half-hour, I’ll show you something.’ I played for a half-hour for free, and they said, ‘You can come back next week… for free.'”

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?”

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