I don't know why I got this list request but I'll go for it and make it an open list. Any Oprah fans? I do think she is the best interviewer alive because she asks the questions only a close friend would dare ask, in a way that makes the subject feel relieved that they have a close friend to talk to.
  1. Rihanna
    Full of wisdom, honesty, and beauty from the jump.
  2. Lindsay Lohan
    Staying sober is incredibly difficult, even if you're not in the public eye. Oprah seems like one of the only public figures to offer Lindsay any support, in a way only Oprah can
    Suggested by @rosiewelles
    Suggested by @shanaz
  4. Kris Jenner
    One of the few times Kris talks about the OJ trial publicly, as well as Kim's divorce, etc. It's awesome.
    Suggested by @sarahgorman
  5. Janet Mock
    One of the best, I devoured this interview! @janetmock
    Suggested by @sarahgorman
  6. Rob Bell
    Suggested by @BWN_7
  7. James Frey
    When she made him come on and apologize for lying about being an addict in his book A Million Little Pieces
    Suggested by @k8mcgarry
  8. Gabrielle Union, Viola Davis, Phylicia Rashad, Alfre Woodard
    A wonderful talk about being black women in Hollywood
    Suggested by @sarahgorman
  9. Obvs
    Suggested by @biz
  10. Toni Braxton
    It reminded me of when my mom chews me out over the phone for spending much of my check on food. Favorite part: When Oprah says, "You had... Gucci flatware. *I* don't even have Gucci flatware!" THE SHADE.
    Suggested by @olive
  11. Stephen Colbert. So great to hear from his brilliant mind out of his then character. Oprah brings out great things.
    Suggested by @mcfearless
  12. Jordan and Jonathan Knight from NKOTB
    NKOTB band members (and brothers) Jordan and Jonathan came on the show to discuss their mutual struggles with Anxiety disorders. Jonathan had a panic attack ON STAGE during the show. This all happened at a time where panic attacks weren't as widely discussed. It's illuminating and heartbreaking.
    Suggested by @mariahnp
  13. Cormac McCarthy
    First ever television interview for one of the greatest writers alive. In his first answer he tells Oprah he's never met a woman he understood. They work to an edgy truce. http://www.oprah.com/oprahsbookclub/Oprahs-Exclusive-Interview-with-Cormac-McCarthy-Video
    Suggested by @helytimes
  14. Iyanla vs Oprah
    When they had it out about why Iyanla left the show, her new show getting cancelled, etc.
    Suggested by @stars
  15. Elie Wiesel and Oprah at Auschwitz
    Oprah has a deep understanding of when to talk, ask questions, and go deeper, and when to just be silent. The haunting silence in this interview makes it an unforgettable interview
    Suggested by @pnw
  16. Whitney Houston
    Suggested by @kiraandlulu
  17. Jk Rowling
    Such a smart and caring lady. She cares for her characters and the rest of the world and thats why her books resonate.
    Suggested by @tantan