Challenges Faced by David Letterman: Obstacles and Turning Points

Life is full of challenges, and David Letterman faced many. Discover key struggles and how they were overcome.

David Letterman is an iconic American television host, comedian, writer, producer, and auto racing team owner best known for hosting late-night talk shows for 33 years. He began with 'Late Night with David Letterman' on NBC in 1982 and concluded with 'Late Show with David Letterman' on CBS in 2015. He hosted a total of 6,080 episodes, surpassing Johnny Carson as the longest-serving late-night talk show host in American television history.

Sections (6)

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

October 24, 1980: Cancellation of The David Letterman Show

On October 24, 1980, The David Letterman Show was canceled after a short run, despite being a critical success.

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1981: Letterman stops drinking alcohol

In 1981, at the age of 34, David Letterman stopped drinking alcohol. He described himself as a "horrible alcoholic" who had been drinking since around age 11 or 13 and stated that he was drunk 80% of the time before quitting.

May 1988: Stalking by Margaret Mary Ray Begins

Beginning in May 1988, David Letterman was stalked by Margaret Mary Ray, who had schizophrenia and committed several acts of intrusion and theft at Letterman's property.

1992: Letterman Leaves NBC for CBS

In 1992, David Letterman left NBC after Jay Leno was chosen to host The Tonight Show. Letterman moved to CBS to host his own late-night show.

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March 27, 1995: Letterman Hosts the Academy Awards

On March 27, 1995, David Letterman hosted the 67th Academy Awards ceremony. His performance was considered a failure by critics and may have caused a decline in the Late Show's ratings.

1995: Late Show Ratings Dip

In 1995, the Late Show's ratings dipped, and The Tonight Show, hosted by Jay Leno, consistently beat Letterman's show in the ratings.

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October 1998: Margaret Mary Ray Dies

In October 1998, Margaret Mary Ray, David Letterman's stalker, died by suicide at age 46. Letterman expressed compassion for her in a statement.

January 14, 2000: Letterman Undergoes Emergency Quintuple Bypass Surgery

On January 14, 2000, a routine checkup revealed a severe artery obstruction in David Letterman's heart. He was rushed to New York Presbyterian Hospital for emergency quintuple bypass surgery.

February 2003: Letterman Uses Guest Hosts Due to Shingles Diagnosis

In February 2003, David Letterman handed the reins of the Late Show to several guest hosts due to being diagnosed with a severe case of shingles.

2005: Restraining Order Filed

In 2005, a woman obtained a restraining order against David Letterman from a New Mexico judge, claiming he sent her coded messages through his television program.

2005: Kidnapping Plot Against Letterman's Son

In 2005, police discovered a plot to kidnap David Letterman's son and demand a $5 million ransom. Kelly Frank, a house painter who had worked for Letterman, was charged in the conspiracy.

October 1, 2009: Blackmail Attempt Announced

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

October 2, 2009: Joe Halderman Pleads Not Guilty

On October 2, 2009, Joe Halderman, a producer for CBS's 48 Hours, pleaded not guilty to attempted grand larceny after being arrested for trying to deposit the fake check from Letterman's sting operation.

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October 3, 2009: Affair with Intern Reported

On October 3, 2009, TMZ reported that David Letterman had a yearlong affair with Holly Hester, a former CBS employee, in the early 1990s when she was his intern and a student at New York University.

October 5, 2009: Letterman Publicly Apologizes

On October 5, 2009, David Letterman dedicated a segment of his show to publicly apologizing to his wife and staff following the revelation of his affairs.

March 2010: Halderman Sentenced

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

June 2011: Joke about the death of Ilyas Kashmiri

In June 2011, David Letterman made a joke about the death of Ilyas Kashmiri, an Al-Qaeda leader who was killed in a drone strike in Pakistan. This joke later led to a death threat against Letterman from an Islamist militant.

August 17, 2011: Islamist militant death threat against Letterman

On August 17, 2011, it was reported that an Islamist militant posted a death threat against David Letterman on a website frequented by Al-Qaeda supporters. The threat was in response to Letterman making a joke about the death of Ilyas Kashmiri, an Al-Qaeda leader.

2015: Letterman discusses his anxiety

In 2015, David Letterman spoke about his long-term struggles with anxiety, hypochondria, and alcoholism, stating he managed them through Transcendental Meditation and low doses of medication. He also mentioned his Presbyterian upbringing.