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.'”