Oprah Winfrey

What better way to celebrate 25 years of The Oprah Winfrey Show than by making a list of our favorite Oprah moments. The only problem? There were too many to choose from! In 25 years on the air, Oprah Winfrey created some classic, unforgettable moments of television that made us laugh, cry, think, vote, donate and stand up and cheer. First we asked our readers for your input — and then TV Guide Magazine's editors had a few meetings where we argued, debated and ultimately shaped a list that got quite a bit of attention. So much so, in fact, that OWN decided to turn our list into a six-part series — TV Guide Magazine's Top 25 Best Oprah Show Moments — that premieres Tuesday, Aug. 28 with back-to-back episodes at 9/8c and 10/9c.

Thanks for the memories, Oprah. Here are three that made the list.

Oprah's Favorite Things
(first episode aired Nov. 23, 1999)
Oprah: "Over the years, Favorite Things became like a franchise of ours. We weren't making any money from it, but it was just exciting to see it happen to other people. I remember one year, I thought, 'We're sending the wrong message. We're sending the message that Christmas is all about stuff.' And so we started trying to figure out how we can give to different groups of people, like nurses one year, and then teachers another year. We were always trying to think of what group of persons can we honor in such a way that it's not just about that stuff, and we want to say thank you. Favorite Things started completely organically for the same reason the book club started completely organically. And that is, this show is just a reflection of who I am. I would say at the very core nature of myself is a spirit of whatever I get, I want somebody else to share it. Life is better when you share it, I say."
Debra: "The Favorite Things shows became as famous for the giveaways as for the audience overreaction and hysteria. The parodies on Saturday Night Live were hysterical! But what's noteworthy, too, is that Oprah gets as excited as the audience does, if not more so!"

Mackenzie Phillips Reveals Incest
(aired Sept. 23, 2009)
Oprah: "I was thinking myself that this is going to cause a big firestorm in her life. She's put the words on the page and she's willing to put that out there into the world. And so I was walking that line between trying to get her to express what she had said in the book, but also trying to have her hold onto herself and not exploit that moment, you know? That's an easily exploitable moment."
Debra: "We chose this moment because it shows Oprah's skills as an interviewer. Oprah handled a tough interview artfully. She challenged Mackenzie from the beginning, making her read out loud from the book. It's a great interview technique. She asked the tough questions everyone wanted to know, but also made her feel comfortable enough to speak openly and honestly. That's the safe environment that was the hallmark of The Oprah Winfrey show."

Oprah and Gayle's Road Trip
(aired Sept. 18, 2006)
Oprah: "My vision was going into quaint little towns, staying at bed-and-breakfasts. Someone would make warm blueberry muffins in the morning and I would pad down in my slippers and sit on the porch in a rocking chair and have sweet tea and talk about what America is and can be. That was my vision. Instead, we were 10 hours a day on the interstate. But really, you know, Gayle always says, 'Oh, gee, I had a good time.' It was wonderful in the category of experience and to know not to do it that way ever again. That's why it was beneficial to me. I learned a lot about myself."
Debra: "We got to see a side of Oprah that only her best friend knows. Just two BFFs on the road, no-holds-barred, no makeup — and no GPS. Who hasn't been on a road trip that's gone bad? Gayle stands up to Oprah like no one else can — and millions of viewers got to go along for the ride."

For more moments, pick up the Aug. 27 issue of TV Guide Magazine, on sale now. And check out a promo of the show here:

First Look: "TV Guide Magazine's" Top 25 Best "Oprah Show" Moments

TV Guide Magazine is counting down the most famous and memorable moments on The Oprah Winfrey Show! Featuring new commentary by Oprah Winfrey and an interview with TV Guide editor-in-chief Debra Birnbaum, the series revisits the most unforgettable interviews, guests, performances and occurrences of the history-making show. Watch a preview! Then, tune in for the premiere Tuesday, August 28, at 9 p.m. ET/PT.

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