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In total, Letterman hosted 6,028 episodes of Late Night and Late Show, Letterman currently hosts the Netflix series My Next Guest Needs No Introduction with David Letterman. His company, Worldwide Pants, produced his shows as well as The Late Late Show with Craig Ferguson and several prime-time comedies, the most successful of which was Everybody Loves Raymond, now in syndication.

Several late-night hosts have cited Letterman's influence, including Conan O'Brien (his successor on Late Night), Stephen Colbert (his successor on The Late Show), Jimmy Fallon, Jimmy Kimmel, and Seth Meyers.

Murray later went on to become one of Letterman's most recurrent guests, guesting on the show's 30th anniversary episode, which aired January 31, 2012 and on the very last show, which aired May 20, 2015. Eastern Time, immediately following The Tonight Show Starring Johnny Carson (a Friday night broadcast was added in June 1987).

It was seen as being edgy and unpredictable, and soon developed a cult following (particularly among college students).

On March 27, 1995, Letterman acted as the host for the 67th Academy Awards ceremony. On his first show after the Oscars, he joked, "Looking back, I had no idea that thing was being televised." He lampooned his stint two years later, during Billy Crystal's opening Oscar skit, which also parodied the plane-crashing scenes from that year's chief nominated film, The English Patient.

Critics blasted Letterman for what they deemed a poor hosting of the Oscars, noting that his irreverent style undermined the traditional importance and glamor of the event. For years afterward, Letterman recounted his hosting the Oscars, although the Academy of Motion Picture Arts and Sciences continued to hold Letterman in high regard and they had invited him to host the Oscars again.

The Late Show lost nearly half its audience during its competition with Leno, attracting 7.1 million viewers nightly in its 1993–94 season and about 3.8 million per night as of Leno's departure in 2009.