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.

▶︎
Cher Calls Dave An Asshole | Letterman

▶︎
Oprah Winfrey Addresses Lesbian Rumors

▶︎
Monologue: Oprah Winfrey on the Oscars - SNL

▶︎
Caroline Kennedy Remembers JFK, Jacqueline and JFK Jr. | David Letterman

▶︎
Oprah Winfrey on Personal Experiences with Racism, Life, The Color Purple & the Future of OWN

▶︎
Oprah Winfrey Got Stuck Paying For Dave's Lunch | David Letterman

▶︎
20 Celebrities That Ruined Their Careers with One Interview

▶︎
Oprah Winfrey on Career, Life, and Leadership

▶︎
People Who Messed With The Royal Guard and Regretted It!

▶︎
12 /14/86: Oprah

▶︎
David Letterman and Oprah Winfrey

▶︎
Oprah Says Being Fired Led to Her First Talk Show Job

▶︎
Peter Sellers was a master of joke telling timing, impersonation, and beautiful accents and language

▶︎
Lisa Bonet on Letterman 4/23/86 First Appearance

▶︎
Monica & Oprah 1986

▶︎
Oprah Winfrey on Weight Loss Journey, Celebrating Her 70th & Which Rumors About Her are True

▶︎
Oprah Winfrey Tells Funny Story During Her First Appearance on Johnny Carson's Tonight Show - 1986

▶︎
Cher Being Brutally Honest for 7 Minutes

▶︎
Robin Williams on Letterman talking about Oprah

▶︎
