Still Cruisin' After All These Years: Top 9 Oprah Moments

From a certain Katie Holmes-loving actress to Winfrey's big weight-loss reveal, we've got your most memorable scenes right here

By Natalie Finn Nov 20, 2009 1:49 PMTags
Tom Cruise, Oprah WinfreyHarpo

With the news that Oprah Winfrey is signing off after...wait, what? She's not pulling the plug on The Oprah Winfrey Show until 2011? Well, shoot, what are we all scrambling around for?!

Still, just thinking about Winfrey's eventual exit after what will be 25 years in syndication has put us in a nostalgic mood, and we've compiled nine of the most memorable Oprah moments, using criteria such as star wattage, emotional heaviness, cultural impact, etc.

Of course, we've probably forgotten your favorite, so be sure to remind us in the comments section. A lot of stuff has happened on Oprah's couch over the last two and a half decades.

Or, in some cases, several inches above her couch...

1. So there was this actor, and he fell in love with an actress, and he decided to prove it by acting like a loon.

2. As A Million Little Pieces author James Frey learned the hard way, you don't ef with Oprah's Book Club.

3. "You get a car! You get a car! You get a car! You get a car!" The Oprah where every audience member scored a free Pontiac G6 was much parodied, and she became even more beloved.

4. Ellen DeGeneres and Portia de Rossi talked about their relationship and showed off their wedding video. It was a beautiful moment that makes you even more glad there's a place like Oprah to do this kind of thing.

5. In 1988, Oprah wheeled out a wagon loaded with 67 pounds of fat to represent the weight she lost to be able to fit into size 2 jeans. The weight loss didn't last, but the image was indelible, and the queen of daytime became as known for her yo-yo dieting as she was for any of her great gets.

6. The nonpartisan-when-it-counts talk-show host tried to get Sarah Palin to admit to being pissed at Bristol's baby daddy...but even Oprah can only do so much.

7. After making a much-hyped appearance on his late-night talker, Oprah brought David Letterman out of hiding in 2007 for his first TV interview in five years.

George Burns/Harpo Productions

8. Thank you for being a friend. Oprah welcomes slumber party gal-pal and tabloid-fixation victim Jennifer Aniston to ask her about the "what Angelina did was very uncool" Vogue cover. "I don't go there," Jen said. "It's a hundred years old, for Christ's sake."

9. Oprah's sit-down with Michael Jackson in 1993 was equal parts uplifting, intriguing and heartbreaking for the 90 million people who tuned in as the King of Pop talked about plastic surgery and the condition that had steadily lightened his skin over the years.

10. You tell us.

We know we probably forgot your prized Oprah moment, be it her taking the beef industry to task during a mad-cow scare in 1996, accepting her lifetime achievement Emmy in 1999, stumping for Barack Obama, flubbing an interview with Elizabeth Taylor or having dinner with one of her heroes, Toni Morrison.

Or maybe you especially like it whenever she suggests a new book for you to read.

Either way, do share what sticks out in your mind from the past 23 years of The Oprah Winfrey Show and beyond in the comments section.

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Plus, take a peek at some of Oprah's most Oprah-esque moments in our gallery.