1. Oprah Winfrey Interviews Michael Jackson (1993)
In this historic interview, Oprah Winfrey sits down with the King of Pop, Michael Jackson. The interview explores Jackson’s personal life, his childhood, and his experiences in the music industry. It delves into his controversies, his struggles with fame, and his desire for privacy. This interview is often cited as one of the most candid insights into the life of a true musical icon, making it an absolute must-see for any fan.
2. David Letterman Interviews Joaquin Phoenix (2010)
Known for his eccentric behavior, Joaquin Phoenix appeared on the Late Show with David Letterman to promote his movie “I’m Still Here.” Throughout the interview, Phoenix delivers unusual and sometimes awkward responses, leaving the audience guessing whether it’s a performance or if he genuinely had a mental breakdown. This interview became a sensation and sparked endless debates among viewers, making it a memorable moment in talk show history.
3. Diane Sawyer Interviews Whitney Houston (2002)
In this emotionally charged interview, Diane Sawyer interviews Whitney Houston, one of the greatest vocalists of all time. The interview touches on Houston’s struggles with addiction, her marriage to Bobby Brown, and the impact of her fame on her personal life. This interview provides a heartbreaking insight into the challenges that come with being in the public eye, making it an essential watch for music lovers and fans of Houston.
4. Britney Spears’ Documentary Interview with Diane Sawyer (2003)
Britney Spears, at the height of her career, opened up to Diane Sawyer in a documentary-style interview. The conversation focuses on her rise to stardom, her relationships, and the constant media scrutiny she faced. The interview sheds light on the price of fame and the mental and emotional toll it can have on celebrities, making it a significant cultural moment.
5. Charlie Rose Interviews Bill Gates (1995)
In this enlightening conversation, Charlie Rose sits down with Bill Gates, the co-founder of Microsoft, to discuss the future of technology and its impact on society. Gates provides valuable insights into his business strategies, vision for the future, and his perspective on the ever-evolving digital landscape. This interview offers a glimpse into the mind of one of the world’s most influential tech entrepreneurs, making it a must-watch for those interested in technology and innovation.
6. Frank Sinatra’s Interview with Barbara Walters (1985)
Barbara Walters’ interview with the legendary Frank Sinatra is a timeless classic. The conversation covers Sinatra’s career, his personal life, and his reputation as a mature performer. Walters dives into the ups and downs of Sinatra’s life, creating an intimate portrait of one of the greatest entertainers of all time. This interview is a perfect blend of journalism and celebrity, making it an iconic moment in television history.
7. Charlie Rose Interviews Robin Williams (2010)
Charlie Rose’s interview with the late Robin Williams is a heartwarming and at times hilarious conversation. Williams opens up about his struggles with addiction and depression while sharing powerful insights into his creative process and comedic genius. This interview showcases Williams’ raw vulnerability and infectious spirit, making it a must-see for anyone who admires his talent and humanity.
8. Johnny Carson Interviews Bette Davis (1981)
Johnny Carson, the king of late-night television, sits down with the iconic actress Bette Davis in this unforgettable interview. Davis, known for her exceptional talent and fiery personality, discusses her career in Hollywood and shares fascinating stories from her time in the industry. Carson’s charm and wit combined with Davis’ captivating presence make this interview a true gem for film enthusiasts.
9. Oprah Winfrey Interviews Tom Cruise (2005)
In one of the most infamous interviews in recent years, Oprah Winfrey welcomes Tom Cruise to her show. Cruise’s erratic behavior during the interview, showcasing his love for Katie Holmes, propelled the interview to a viral status, sparking numerous parodies and discussions. Despite its controversy, this interview became a defining moment in celebrity interview history, guaranteeing its place on this must-see list.
10. Ed Bradley Interviews Michael Jordan (2003)
Renowned journalist Ed Bradley sits down with basketball legend Michael Jordan for a captivating interview. Jordan reflects on his remarkable career, his competitiveness, and the challenges he faced both on and off the court. This interview provides unique insights into the mind of one of sports history’s greatest athletes, making it a must-watch for any sports fan.