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    9 Images

    David Letterman's Women Troubles

    From affairs with staffers to female "Late Show" guests, Letterman has often crossed the line

  • David Letterman
    In the latest development in the David Letterman saga, some universities are vowing to keep a close watch on their students when they take on an internship at the "Late Show." Last week, the late-night comedian apologized to wife Regina Lasko during a taping of his "Late Show" at the Ed Sullivan theater. The apology came days after CBS producer Robert "Joe" Halderman pleaded not guilty to attempting to extort $2 million from Letterman in exchange for keeping quiet about his sexual affairs with members of his female staff. David Letterman undoubtedly offended his wife Regina Lasko by making a joke of his public confession to the affairs. While Letterman's camp insists the relationships took place before his March marriage, Lasko was his long-time girlfriend for years. Despite his apology, Letterman continued to joke Monday about the affairs with his female staff. Somehow, we don’t think Lasko is laughing.   (Source: AP)
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  • Holly_Hester
    Holly Hester is a former “Late Show” intern who admitted to having a sexual relationship with Letterman for over a year during the 1990s. Hester says she was “madly in love” with Letterman at the time and would have married him. A student at NYU at the time, she claims Letterman called off the romance because of the age difference. Letterman referred to his relationships with his staffers as “creepy.” Hey, one man’s creepy is another woman’s mad love.   (Source: TMZ. Click here for more from TMZ.com)
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  • Holly Hester
    In this photo obtained by TMZ, former "Late Show" intern Holly Hester is seen lounging on David Letterman's office couch. Hester said she was "madly in love" with Letterman before he ended his affair with her while she was an NYU student in the 1990s. (Source: TMZ)
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  • Holly Hester
    In this photo obtained by TMZ, former "Late Show" intern Holly Hester is seen smoking a cigar at David Letterman's office. Hester said she was "madly in love" with Letterman before he ended his affair with her while she was an NYU student in the 1990s. (Source: TMZ)
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  • Stephanie Birkitt
    Stephanie Birkitt is a former assistant to David Letterman who is said to be the woman at the center of an affair to which the late-night comedian confessed last Thursday. Birkitt began her career with Letterman as an intern, before working for CBS News, “48 Hours” and the “Late Show.” She was also said to have lived with Letterman’s accused extortionist, Robert “Joe” Halderman.   (Source: TMZ.com. Click here for more from TMZ.)
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  • Merrill_Markoe
    Merrill Markoe was hardly just a fleeting affair in Letterman’s life. Indeed, the comedienne and writer was one of the brain-children behind “The Late Show” and was involved with the host for ten years. Her work on the show earned her 5 Emmy awards, but did not save her relationship with Letterman.
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  • Sarah Palin
    Former Vice-Presidential candidate Sarah Palin knows first-hand how Letterman often makes light of sticky situations. The two got into a war of words earlier this year after Letterman made jokes about her teenage daughter being “knocked up” by New York Yankee Alex Rodriguez. While Letterman invited the Palins to his show, the former Alaska governor said she had no intention whatsoever to “provide a ratings boost” to Letterman by appearing on his show.
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  • Oprah
    Oprah Winfrey became the butt of one of the dumbest jokes of all time at no fault of her own. At the 57th Annual Academy Awards in 1995, he mocked the talk-show queen’s name by comparing it to Uma Thurmans.    He chanted “Uma, Oprah,” awkwardly playing off of the stars' names ending in the same sound.    Oprah famously avoided Letterman’s show for 16 years, noting her discomfort at being the target of his jokes. The two finally buried the hatchet in 2005, when she appeared on his show.
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  • Cher
    Cher may have been keen to a secret that other women did not know, which she admitted in 1986 on her first Letterman appearance. The singing and acting legend told him that she avoided the show because she thought he was an “a**hole” and said she even told a member of his staff.   (Source: AP)
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  • Published
    9 Images

    David Letterman's Women Troubles

    From affairs with staffers to female "Late Show" guests, Letterman has often crossed the line

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  • David Letterman's Women Troubles
  • David Letterman
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  • Holly Hester
  • Holly Hester
  • Stephanie Birkitt
  • Merrill_Markoe
  • Sarah Palin
  • Oprah
  • Cher