Over the 25 years that Oprah Winfrey’s popular TV show ran, several engaging and sometimes controversial topics created honest, genuine conversations. Her first episode, “AM Chicago,” aired on January 7, 1986. Her final episode, “Oprah’s Final Message,” aired 25 years later keeping true to her key message throughout the 25 years: “You are not alone.”
For 25 years, Winfrey gave away cars, asked the questions we all wondered, and raised awareness of important issues many faced. For the 20 most memorable episodes of “ The Oprah Winfrey Show ,” I went straight to the viewers. These are the 20 episodes that viewers rank the highest on IMDb. They’re ranked from lowest to highest with the #1 episode being the highest ranked. (Also, read “ 14 Celebrities Who Did Not Make It Until They Were in Their 30s ” to learn more about Oprah Winfrey.)
The Auschwitz Episode
Elie Wiesel, author of “Night” wrote that book based on his recollections of surviving Auschwitz at the age of 15. The talk show host accompanied him on a return visit to the former concentration camp in one of the best Oprah Winfrey episodes.
- Air Date: May 24, 2006
- Guests: Elie Weisel
- IMDb Rating: 7.3
The Oscar Countdown Show
This highly-rated episode took a closer look at the nominations for the 76th Academy Awards. “The Lord of the Rings” was one of the big winners that year, but “Mystic River,” “Monster,” and “Cold Mountain” also produced several nominees and winners.
- Air Date: February 27, 2004
- Guests: Sean Astin, Ben Kingsley, Holly Hunter, and Liv Tyler
- IMDb Rating: 7.3
Oprah’s Ultimate Australian Adventure
For two days, the show took over the Sydney Opera House. Several famous Australians joined for a stunning rendition of “I Still Call Australia Home.” The trip to Australia lasted four days in all and the other episode added guests like Russell Crowe and paid tribute to the late Steve Irwin through appearances with his wife and two children.
- Air Date: January 21, 2011
- Guests: Pete Evans, Hugh Jackman, Hugh Jackson, Nicole Kidman, Olivia Newton-John, and Keith Urban
- IMDb Rating: 7.5
High Style on a Budget and “Across the Universe”
Fashion takes center stage for part of this memorable episode of “The Oprah Winfrey Show.” The other part focuses on the movie “Across the Universe,” a musical romance featuring music from the Beatles.
- Air Date: September 14, 2007
- Guests: Dana Fuchs, Martin Luther, Jim Sturgess, Julie Taymor, Vera Wang, and Evan Rachel Wood
- IMDb Rating: 7.5
The “Hairspray” Episode
Fans loved this celebration of the 2007 movie based on the award-winning Broadway show. Several actors received nominations, including Zac Efron for an MTV Movie Award, and the song “You Can’t Stop the Beat” won a People’s Choice Award.
- Air Date: July 18, 2007
- Guests: Nikki Blonsky, Zac Efron, Tramaine Montell Ford, Elijah Kelley, Michelle Pfeiffer, Queen Latifah, Adan Shankman, and John Travolta
- IMDb Rating: 7.5
The “General Hospital” Episode
The long-running soap opera about Port Charles, New York, aired its first episode in 1963. “General Hospital” stars shared their insights on the show. In the “Dreams Come True” segment, a Defiance College coach achieved his dream of pitching for the Tigers during spring training.
- Air Date: February 23, 2004
- Guests: Maurice Benard, Steve Burton, James Evans, and Rick Hearst
- IMDb Rating: 7.5
“The Movie Album” Episode
In this episode, singer Barbra Streisand discussed her new release “ The Movie Album .” It features classics like “Moon River” and Charlie Chaplin’s “Smile.”
- Air Date: October 14, 2003
- Guests: Daniel Browning Smith, Dennis Rogers, and Barbra Streisand
- IMDb Rating: 7.5
The Madonna Episode
Madonna appeared on Oprah’s talk show in December 1996 participating in her first long interview. Until this memorable episode of “The Oprah Winfrey Show,” she’d only given brief interviews. It also marked her first interview since giving birth to her daughter.
- Air Date: December 13, 1996
- Guests: Madonna and Sage Stallone
- IMDb Rating: 7.5
The “Brokeback Mountain” Episode
After its release in 2005, “Brokeback Mountain” became an Oscar contender. Shortly before the Oscars aired, Winfrey invited the main cast to talk about their movie that ended up winning three Oscars.
- Air Date: January 27, 2006
- Guests: Jake Gyllenhaal, Anne Hathaway, Heath Ledger, Tyler Perry, and Michelle Williams
- IMDb Rating: 7.6
Anderson Cooper Talks About His Family History
It wasn’t well known then that CNN’s Anderson Cooper’s mom was the legendary designer Gloria Vanderbilt. Both mother and son appeared in this episode to talk about the tragic suicide of Anderson’s brother and the family history. The episode also covered the dangers children face on the internet.
- Air Date: May 23, 2006
- Guests: Anderson Cooper and Gloria Vanderbilt
- IMDb Rating: 8
The “Mona Lisa Smile” Episode
Julia Roberts portrayed a 1950s professor in “Mona Lisa Smile.” She encourages her female students to ignore what they’ve been told is expected of young women at the time. The cast got together to discuss society’s expectations of women.
- Air Date: November 18, 2003
- Guests: Kirsten Dunst, Julia Roberts, and Julia Stiles
- IMDb Rating: 8
“The Comeback Kid” Episode
Before he was Iron Man, Robert Downey Jr. was an addict whose problems were piling up. After serving time at Corcoran State Prison and a year-long stay in a live-in treatment program, he sat down in one of the most memorable Oprah episodes to talk about being clean for two years.
- Air Date: November 23, 2004
- Guests: Robert Downey Jr.
- IMDb Rating: 8.1
The “Women Across the Globe” Episode
Indian actress and Miss World winner Aishwarya Rai Baschand talked about women around the world. Additional women from countries like Iceland, Portugal, and Saudi Arabia appear to talk about their perceptions of American women.
- Air Date: April 24, 2005
- Guests: Aishwarya Rai
- IMDb Rating: 8.2
The New Faces of HIV/AIDS Episode
This wasn’t the first time Magic Johnson sat down with Winfrey to discuss his HIV diagnosis and the advancements in HIV and AIDS treatments . He returned in 1999 with several people diagnosed with HIV, including a pregnant woman who learned she was HIV positive after becoming pregnant. Her boyfriend of five years had given it to her.
- Air Date: September 17, 1999
- Guests: Magic Johnson
- IMDb Rating: 8.3
The “Stars of Australia” Episode
The blockbuster “Australia” was set in WWII when Japan bombed Darwin, Australia. It starred Nicole Kidman and Hugh Jackman. In addition to talking about the movie, Kidman also had just become a mom to Sunday Rose.
- Air Date: November 10, 2008
- Guests: Hugh Jackman and Nicole Kidman
- IMDb Rating: 8.3
“The Mirror Has Two Faces” Episode
Singer Barbra Streisand is also a talented actor. In this popular Oprah episode, she discussed her new movie “The Mirror Has Two Faces.” That movie would land her an Oscar nomination for “Best Music” for the duet with Bryan Adams titled “I Finally Found Someone.” It also earned Lauren Bacall a nomination for “Best Supporting Actress.”
- Air Date: November 11, 1996
- Guests: Barbra Streisand
- IMDb Rating: 8.3
The “Walk the Line” Episode
Johnny Cash’s life story was told in the blockbuster movie “Walk the Line.” The cast stopped by to talk about their movie and the music they performed in it.
- Air Date: October 10, 2005
- Guests: Nate Berkus, Ricky Martin, Joaquin Phoenix, and Reese Witherspoon
- IMDb Rating: 8.4
The “Finding Neverland” Episode
Author J.M. Barrie’s life and inspiration for Peter Pan was told in “Finding Neverland.” The cast of the movie joined Winfrey to talk about it.
- Air Date: November 2, 2004
- Guests: Johnny Depp, Freddie Highmore, and Kate Winslet
- IMDb Rating: 8.4
The “Just One Thing” Episode
In this episode, Winfrey reflects on a question that a past audience member asked her. What was her one “life-defining moment?” She shares the court battle she found herself in with the beef industry and gets others to share theirs.
- Air Date: August 31, 2002
- Guests: Katie McGovern
- IMDb Rating: 8.6
The Bette Midler Episode
Midler performed her hit “The Rose” live during this episode. The women also discuss a topic that most women experience: aging.
- Air Date: December 8, 1995
- Guests: Bette Midler
- IMDb Rating: 9.2
Those are the episodes fans rank as the best episodes of “The Oprah Winfrey Show.” After more than 25 years in the industry, Oprah Winfrey has gained an impressive net worth by addressing topics people want to talk about. See how high she ranks in “ The 20 Celebrities With the Highest Net Worth .”
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