March 31, 2003 - Letterman returns to his show after being out for nearly a month due to shingles.
March 17, 2005 - Kelly Frank, a house painter who worked on Letterman's Montana ranch, is charged with plotting to kidnap Letterman's son and hold him for ransom.
September 12, 2005 - Frank pleads guilty to a lesser charge and is sentenced to ten years in prison. In 2007, he escapes, but is later recaptured.
October 1, 2009 - Letterman admits on air that he has had sexual relationships with female staff members and that someone has been attempting to blackmail him over the affairs.
October 5, 2009 - Letterman apologizes to his wife, Regina Lasko, and female staffers in front of a live studio audience.
March 9, 2010 - Robert "Joe" Halderman, a former CBS News producer accused of trying to blackmail Letterman, pleads guilty to attempted second-degree grand larceny and is sentenced to six months in jail, five years' probation and 1,000 hours of community service.
September 2, 2010 - Robert "Joe" Halderman is released after serving four months of his six-month prison sentence.
April 2012 - Extends his contract with CBS through 2014.
December 2, 2012 - Is honored at the Kennedy Center Honors gala along with Buddy Guy, Dustin Hoffman, Natalia Makarova and the musical group Led Zeppelin.