David Letterman Affair, Extortion Part of Host's Controversial Legacy

On the October 1 broadcast of the Late Show, David Letterman admitted to his audience to having sexual relationships with his female staffers. ABC News reports that the admission came as a result of a blackmail extortion attempt by a CBS producer named Robert Halderman. The latest Letterman apology is just another controversial moment for the late night host. Here is a list of the controversial highlights (and lowlights) of David Letterman's 27-year career.

Late Night with David Letterman (NBC, 1982-1993)

July 28, 1982, Andy Kaufman v. Jerry Lawler
As part of an Andy Kaufman performance piece that was set up well in advance, wrestler Jerry Lawler slaps neckbrace-wearing Andy Kaufman. Kaufman later throws a cup of water in Lawler's face and goes off on an obscenity-laced tirade. The frighteningly realistic hoax puts Letterman's new late night show on the map. Youtube clip.

July 28, 1987, Crispin Glover
Five years to the day after Kaufman's memorable appearance, actor Crispin Glover, best known to moviegoers as George McFly from Back to the Future, attempts a strange performance piece of his own. Crispin Glover appears with bizarre mannerisms, challenging Letterman to an arm wrestling competition and then kicking in front of Letterman's face with big platform shoes. Letterman cuts to commercial, and Glover is gone. Youtube video. Glover appears a few weeks later, but Letterman is dismissive and condescending. Youtube video.

The Late Show with David Letterman (CBS, 1993-Present)

March 31, 1994, Madonna
Controversial pop star Madonna appears on Letterman's new CBS show. Madonna is bleeped 13 times, controlling the conversation, steering toward sexual and scatological topics, and insinuating Letterman wears a wig. Letterman later apologizes, telling USA Today that he should have stopped it sooner. Youtube video.

September 17, 2001
After the events of September 11, Letterman starts his show without the usual musical fanfare and applauding audience, instead seriously reflecting upon the terrorist attacks. Youtube video.

December 1, 2005, Oprah Winfrey
Oprah's first visit to David Letterman's couch since 1989. Winfrey had grown estranged by Letterman's jabs at her weight and her talk show. Things had also been made tense by Letterman's infamous Uma-Oprah dud of a joke as host of the Academy Awards in 1995. Youtube video.

February 11, 2009, Joaquin Phoenix
Actor Joaquin Phoenix appears on Letterman, seemingly in character as a drugged-out, bearded space cadet. Phoenix, who appears incoherent for the entire interview, elicits the strange interviews of early, post-Carson Letterman. Youtube video.

June 9, 2009, Dave v. Sarah Palin
As part of Letterman's monologue, he makes an errant sexual comment about Sarah Palin's daughter visiting a baseball game. Although the joke is directed at 18-year-old Bristol Palin, in reality, the 14-year-old daughter Willow was the daughter at the game. Youtube video.

June 11, 2009, Dave v. Sarah Palin
After the fallout from the misfired joke about Willow Palin, Letterman sits down at his desk, addressing the jokes he made and clarifying what he meant. In his pseudo-apology, Letterman gets big laughs while defending himself against Sarah Palin's inference of him telling rape jokes. Youtube video.

October 1, 2009
David admits to having sexual affairs with female staffers as a result of a CBS producer allegedly trying to blackmail him and extort $2 million. Again, Letterman, in his admission of guilt, gets nervous laughs and applause while explaining himself. Youtube video.

Sources:
ABC News, "Robert Halderman: David Letterman's Alleged Extortionist is CBS Producer"