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1.
Pretentious fuck whom many people find amusing in a "I'm semi-conscious because its five past fuck-knows-what-hour and hey here's some late night TV - oh this guys funny, but only because my brain is concentrating most of its energy on digestion" sort of way. Characteristics of the Letterman include corny predictable jokes, cabaret music, boring celebrity guests and a good old wank. Apparently the Letterman likes his studio nice and cold, so when a journalist asked why it was so cold in there some PR person was all grovelling-like "because Letterman likes it that way" - what sort of self-centered fucking bullshit is that? Do you control the fucking atmospheric temperature now as well as the airwaves between 3 and 4 am?
"I hope my girlfriend gets this letter man"
by Lawson March 30, 2005
 
2.
A person who constantly flames/cheap shots other people to stroke his ego. Whereas a cheap shot is a Leno, a person who cheap shots others is a Letterman.
God, what a Letterman. That moderator keeps insulting people and locking topics for no reason.
by OLOL March 21, 2007
 
3.
Having sex with a coworker or subordinate.
John:"I heard Bob pulled a Letterman with Lisa"
Trevor:"Uhumm...heard that too. Heard he banged her in the meditation room"
John:"Why there?"
Trevor:"Because there isn't a security camera and nobody's ever there"
John:"Aha I see....I would also pull a Letterman with Lisa"
Trevor:"You know it"
by IPullMoreLettermansThenYou October 03, 2009
 
4.
1. A funny (and funny-looking) guy who hosts this show that appears late at night on the CBS television network. Also known as Dave, David, David Letterman.

2. Jay Leno's arch-nemesis.
"We watched that Letterman show last night, and it was hilarious!"
by star8706 February 01, 2003
 
6.
the funniest late night show host today. much funnier than jay leno.
I tried to watch jay leno, but i got a real sense of how fake LA is very quickly. I hurried and flipped it to Letterman, who always makes me laugh.
Have you seen his "Will it Float?" skit? It is hilarious!
by HappyHenry35 April 20, 2003