Most Talked-About Controversies Linked to David Letterman

By Popular Timelines Editorial Team · Updated: May 5, 2026

Controversies are a part of history. Explore the biggest scandals linked to David Letterman.

David Letterman is an American television icon, renowned for his influential and lengthy career as a late-night talk show host. He helmed both "Late Night with David Letterman" on NBC and "Late Show with David Letterman" on CBS for a combined 33 years. In total, Letterman hosted an impressive 6,080 episodes, establishing him as the longest-serving late-night talk show host in American television history. His unique comedic style and innovative approach to the talk show format solidified his place as a major figure in entertainment.

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Full Timeline Early Life & Education Career & Achievements Success & Recognition Challenges & Struggles Controversies & Scandals

January 2, 2008: Letterman returns to Late Show with beard after WGA strike

On January 2, 2008, David Letterman returned to the Late Show after the Writers Guild of America strike, sporting a newly grown beard in solidarity.

January 7, 2008: Letterman's beard is shaved off on Late Show

On January 7, 2008, David Letterman's beard, grown in solidarity with the Writers Guild of America strike, was shaved off during the Late Show.

2008: Pregnancy of Bristol Palin

In 2008, Bristol Palin's pregnancy as an unmarried teenager caused some controversy during the United States presidential election.

2008: CBS Business Conduct Statement details romantic relationship policy

In 2008, the CBS Business Conduct Statement specified that supervisors must disclose any romantic or sexual relationship with a direct or indirect subordinate to the company's Human Resources Department.

October 1, 2009: Letterman reveals blackmail attempt

On October 1, 2009, David Letterman announced on his show that he was the victim of a blackmail attempt. An individual threatened to reveal Letterman's sexual relationships with female employees unless he paid $2 million. Letterman confirmed the affairs and contacted the Manhattan District Attorney's office, leading to a sting operation.

October 2, 2009: Joe Halderman arrested

On October 2, 2009, Joe Halderman, a producer of CBS's 48 Hours, was indicted by a Manhattan grand jury after Letterman's testimony regarding the blackmail attempt. Halderman pleaded not guilty to attempted grand larceny.

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October 3, 2009: TMZ reports Letterman affair with intern

On October 3, 2009, TMZ reported that David Letterman had a year-long affair with Holly Hester, a CBS intern and New York University student, in the early 1990s.

October 5, 2009: Letterman apologizes publicly

On October 5, 2009, David Letterman made a public apology to his wife and staff regarding his affairs during a segment of his show.

2009: Sexually themed jokes about Sarah Palin's daughter

In 2009, David Letterman told two sexually themed jokes about a daughter of Sarah Palin on his TV show, including a joke that Palin's daughter had been "knocked up" by MLB player Alex Rodriguez. It was unclear which daughter the joke referred to.

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March 2010: Halderman sentenced for blackmail attempt

In March 2010, Joe Halderman pleaded guilty and was sentenced to six months in prison, probation, and community service for attempting to blackmail David Letterman.

June 2011: Death of Ilyas Kashmiri

In June 2011, Ilyas Kashmiri, an Al-Qaeda leader, was killed in a drone strike in Pakistan. David Letterman made a joke about his death, which led to a death threat against Letterman.

August 17, 2011: Death threat against Letterman

On August 17, 2011, an Islamist militant posted a death threat against David Letterman on a website frequented by Al-Qaeda supporters, calling on American Muslims to kill him for making a joke about the death of Ilyas Kashmiri.