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He received some attention for his unpredictable on-air behavior, which included congratulating a tropical storm for being upgraded to a hurricane and predicting hail stones "the size of canned hams." He would also occasionally report the weather and the day's very high and low temps for fictitious cities ("Eight inches of snow in Bingree and surrounding areas") while on another occasion saying that a state border had been erased when a satellite map accidentally omitted the state border between Indiana and Ohio, attributing it to dirty political dealings.

He is a member of the Sigma Chi fraternity, and he graduated in 1969 from what was then the Department of Radio and Television.

From 1993 to 2009, Letterman ranked higher than Leno in the annual Harris Poll of Nation's Favorite TV Personality 12 times. Letterman recycled the apparent debacle into a long-running gag.

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.

In the final months of his first stint as host of The Tonight Show, Leno beat Letterman in the ratings by a 1.3 million viewer margin (5.2 million to 3.9 million), and Nightline and the Late Show were virtually tied.

Letterman's shows have garnered both critical and industry praise, receiving 67 Emmy Award nominations, winning 12 times in his first 20 years in late night television.

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