text: In a September 7, 1993, interview, Rosie Perez mentioned that she had attended a DJ party called Funkmaster Flex Night to which Letterman jokingly displayed his ignorance by pretending to know with the response “Funk. Master. Flex night… Hard to get a ticket to Funkmaster Flex Night.” This was later sampled by the DJ himself and it became a famous needle drop in the hip hop community. Letterman was made aware of this cultural moment 26 years later by Desus and Mero when he appeared on their show.
  The episode featuring Madonna on March 31, 1994;
  A visit from Drew Barrymore on April 12, 1995, during which she "jump[ed] on his desk and flash[ed] her breasts" in a "birthday gift he'll never forget";
  The episode on December 31, 1999, airing in prime-time.
  The episodes airing the week of February 21, 2000, which began with Letterman's return to the air after his quintuple bypass surgery, with Bill Cosby hosting the show of February 22, as the show's first ever substitute host, and Regis Philbin hosting on February 24.
  His return to the airwaves on September 17, 2001, following the September 11 attacks in a show that featured Dan Rather, Regis Philbin, The Boys' Choir of Harlem, and Odetta—it was "hailed by the New York Daily News as 'one of the purest, most honest and important moments in TV history'."