Oprah Winfrey made history with The Oprah Winfrey Show, which was the highest-rated television program of its kind in history and ran in national syndication for 25 years from 1986 to 2011. The talk show host has since created other career paths from the success of the show as a television producer, actress, author and philanthropist.
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Oprah celebrated 67 years of life on Jan. 29, 2020 as one of the greatest to ever do it with her candid interviews asking the questions that millions of Americans wanted answers to while making each of her guests comfortable enough to share their personal lives. Her interviews were always entertaining, tear jerking and filled with new, interesting information about some of the most mysterious and private celebrities in entertainment. Enjoy this thread of Oprah’s classic interviews to celebrate more life for the entertainment mogul.
In 1999, Oprah sat down with Mariah Carey and her mom, Pat, to talk about the discrimination their interracial family had experienced. Mariah speaks candidly on how growing up in a predominantly white town and being biracial affected her upbringing.
3. Oprah Asks The Tough Questions In Whitney Houston Interview
Music icon Whitney Houston opened up to Oprah about her tumultuous 14-year marriage to R&B star Bobby Brown in an interview back in 2009.
4. Janet Jackson's Controversial Halftime Show
During the 2004 Super Bowl halftime show, Justin Timberlake exposed Janet Jackson’s breast to the world, igniting a firestorm of controversy. Janet Jackson gave Oprah an exclusive interview on her side of the story.
5. Madea Makes Her First TV Appearance
Take a look back at Oprah’s hilarious, one-on-one exclusive interview with Tyler Perry’s Madea.
6. Jennifer Aniston Finds Total Peace
Oprah Winfrey has a way to make her guests truly comfortable enough to open up and discuss extremely personal and emotional moments on the show. Jennifer Aniston discusses finding complete peace after a rough year.
7. Rihanna Discusses Forgiving Chris Brown
This interview where Rihanna shares forgiving Chris Brown still makes us emotional. Many people think that Chris Brown’s attack on Rihanna was unforgivable, but Rihanna tells Oprah she learned to let go of her anger and forgive Chris.
8. Oprah Reveals She Has A Half-Sister
An emotional look into Oprah’s personal life as she introduces her long, lost half-sister Patricia to the world.
9. Oprah Sits Down With Barack and Michelle Obama
In Oprah’s farewell season of The Oprah Winfrey Show, she sits down with the standing President and First Lady for the first time on the show. A true legend.
10. Donald Trump Teases A Presidential Bid During The Oprah Winfrey Show
Former President Donald Trump talks about the potential to holding the highest office in the land. Listen to just how far back his presidential aspirations reach in a 1988 appearance on ‘The Oprah Winfrey Show’, where he shares his thoughts on running for office.
11. Nelson Mandela Coined Most Humble Man By Oprah
This interview is from Nelson Mandela’s appearance on The Oprah Winfrey Show in 2000 where Oprah shares that he is the most humble man she’s ever met.
12. Dennis Rodman Sheds Light On His Sexuality
Dennis Rodman sits with Oprah Winfrey on her show in 1996 and reveals more about his sexual identity.
13. The Kardsashians On The Effect Of Their Mom's Affair
The Kardashian siblings open up about how Kris’s affair and their parents’ and subsequent divorce has had a lasting impact on them.
14. Willow Smith Steals The Show
An adorable clip of the world being introduced to a young Willow Smith during an interview on the show.
15. Stories We Never Heard Before
Keenen Ivory, Damon, Shawn and Marlon Wayans wouldn’t be the same people without their mother, who was demanding yet extremely supportive of them as boys.
