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To celebrate the media mogul's guest-starring role on tonight's '30 Rock,' we look back at her gabfest's most outrageous moments
By Kate Ward Updated November 05, 2008 at 11:00 PM EST
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Oprah Interviews Elizabeth Taylor

Oprah Interviews Elizabeth Taylor

Feb. 1, 1988

Oprah experienced one of her worst interviews when a tight-lipped Elizabeth Taylor appeared on her show (Oprah has admitted, ''It's still painful to watch''). Certainly, the tragic hairstyles didn't help.

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Wheeling Out the Fat Wagon

Wheeling Out the Fat Wagon

Nov. 15, 1988

Oprah pulls out a wagon with 67 pounds of fat to represent her weight loss. In turn, she helps viewers begin their diets by drastically reducing the appeal of bacon.

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Oprah Champions Hot Alaskan Love

Oprah Champions Hot Alaskan Love

Feb. 17, 1989

If only Oprah had pitched this idea to Mike Fleiss (think Who Wants to Marry a Hot Cold Man?): A slew of Alaskan men hardly received a chilly reception from female Oprah fans, who flocked to the airport in droves to greet the host's single-and-looking guests.

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Oprah Breaks Down

Oprah Breaks Down

May 21, 1990

Before Ellen had Iggy, Oprah had Truddi Chase. When the author of When Rabbit Howls made a guest appearance on Oprah's show to talk about her tragic childhood — Chase was continually raped by her stepfather — the host broke down in tears during her introduction and had to ask her cameraman to stop filming.

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Oprah Slams Beef

Oprah Slams Beef

1998

When beef sales plummeted after O said that mad-cow disease ''stopped me cold from eating another burger,'' a group of Texas cattle ranchers sued the talk show titan — and lost. What, are you surprised?

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Everybody Gets a Car!

Everybody Gets a Car!

Sept. 13, 2004

Oprah jump-starts season 19 by giving a Pontiac G6 to every member of her convulsing audience, some of whom literally climb on the vehicles in ecstasy.

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Dr. Oz Talks BMs

Dr. Oz Talks BMs

May 3, 2005

As if Oprah's fat wagon wasn't too much information, the host welcomed Dr. Mehmet Oz on her program to discuss the appearance and sound of — prepare yourself — healthy poop (hint: the doc references an Acapulco cliff diver as an analogy).

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Tom Goes Crazylove on Oprah's Couch

Tom Cruise jumping on the couch (May 2005)
Credit: Harpo Productions

May 23, 2005

Tom Cruise shakes Oprah like a rattle and jumps on her couch to declare his love for Katie Holmes. Comedians and gossip bloggers worldwide extend their gratitude.

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Oprah Chooses William Faulkner

Oprah Chooses William Faulkner

June 3, 2005

Oprah's audience got the most difficult reading assignment of their lives — this isn't Eat Pray Love, folks! — when the host chose a trio of novels by the notoriously difficult-to-read Faulkner for her book club. No wonder the book only stayed on the Publishers Weekly best-seller chart for a mere three weeks.

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Terry McMillan Confronts Her Gay Ex-Husband

Terry McMillan Confronts Her Gay Ex-Husband

Nov. 9, 2005

Talk about squirm-inducing television. The author of How Stella Got Her Groove Back used an episode of Oprah's show to spar with her ex-husband, who admitted to being gay after six years of marriage.

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11

James Frey, Oprah Winfrey, ...
Credit: George Burns/AP

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    1 of 11 Oprah Interviews Elizabeth Taylor
    2 of 11 Wheeling Out the Fat Wagon
    3 of 11 Oprah Champions Hot Alaskan Love
    4 of 11 Oprah Breaks Down
    5 of 11 Oprah Slams Beef
    6 of 11 Everybody Gets a Car!
    7 of 11 Dr. Oz Talks BMs
    8 of 11 Tom Goes Crazylove on Oprah's Couch
    9 of 11 Oprah Chooses William Faulkner
    10 of 11 Terry McMillan Confronts Her Gay Ex-Husband
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