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Keith Olbermann David Letterman

Keith Olbermann: 'I Screwed Up'

The Huffington Post | Jack Mirkinson | Posted 06.04.2012 | Media

Keith Olbermann told David Letterman on Tuesday that he "screwed up really big" in deciding to join Current TV. (See the comments in the video below.)...

WATCH: Olbermann Returns To TV, Talks About Why He Left MSNBC

The Huffington Post | Jack Mirkinson | Posted 07.19.2011 | Media

Keith Olbermann made his first television appearance since his exit from MSNBC on Wednesday, chatting with David Letterman on "The Late Show" about hi...

John McCain Cancels Letterman Appearance, Keith Olbermann Fills In

Huffington Post | Posted 05.25.2011 | Media

Update: In addition to repeatedly mocking McCain for skipping out on his scheduled appearance Wednesday, Letterman also devoted, fittingly, his nightl...

Keith Olbermann: Most People In News Are Not Smart Enough For Analysis

Huffington Post | Posted 05.25.2011 | Media

Keith Olbermann sat down with David Letterman last night and slammed the members of the news business, saying, "Most of us in news are not smart enoug...