Oprah Winfrey on Letterman, January 13, 1986
Oprah's first appearance on the show, here promoting "The Color Purple" and her syndicated talk show in Chicago.
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Cher Calls Dave An Asshole | Letterman
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Oprah Winfrey Addresses Lesbian Rumors
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Monologue: Oprah Winfrey on the Oscars - SNL
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Caroline Kennedy Remembers JFK, Jacqueline and JFK Jr. | David Letterman
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Oprah Winfrey on Personal Experiences with Racism, Life, The Color Purple & the Future of OWN
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Oprah Winfrey Got Stuck Paying For Dave's Lunch | David Letterman
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20 Celebrities That Ruined Their Careers with One Interview
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Oprah Winfrey on Career, Life, and Leadership
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People Who Messed With The Royal Guard and Regretted It!
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12 /14/86: Oprah
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David Letterman and Oprah Winfrey
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Oprah Says Being Fired Led to Her First Talk Show Job
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Peter Sellers was a master of joke telling timing, impersonation, and beautiful accents and language
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Lisa Bonet on Letterman 4/23/86 First Appearance
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Monica & Oprah 1986
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Oprah Winfrey on Weight Loss Journey, Celebrating Her 70th & Which Rumors About Her are True
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Oprah Winfrey Tells Funny Story During Her First Appearance on Johnny Carson's Tonight Show - 1986
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Cher Being Brutally Honest for 7 Minutes
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Robin Williams on Letterman talking about Oprah
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