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Oprah Winfrey and David Letterman
© Retna
Oprah Winfrey and David Letterman
Great Oprah Moments
A look back at compelling, goofy and spectacular highlights of
the TV queen's career
 

By Kati Johnston
Special to MSN Entertainment

Photo Gallery: Memorable Oprah Moments

It seems as if Oprah Winfrey has always been with us -- and this wouldn't be the same country without her, sort of like not having the Statue of Liberty in New York Harbor. But as we drink in the current swirling around Oprah's taking on of the publishing industry over James Frey's tattered memoir, it's worth pausing to remember that she's had many golden moments over the past 20 years -- moments that you can now relive through her anniversary DVD collection. Here are a few of our favorites since her first broadcast in 1986:

From "The Oprah Winfrey Show"
Mega-weight Loss (1988): After four months of eating virtually nothing, Oprah enters her studio wearing slim designer jeans and pulling a wagon onto the stage filled with 67 pounds of & fat.

First Great Car Giveaway (2005): First, Oprah calls 11 women to the stage and tells them they're getting brand-new cars (wildly promoted Pontiacs). Then, everyone in the audience receives a gift box, only one of which (supposedly) contains a key to a 12th car. But it turns out every box contains a key. Special highlight: Oprah screaming over and over again, "Everybody gets a car! Everybody gets a car!" Hey, what about me?

Cruise Unglued (2005): Oprah's been criticized for being tough on nobodies while practically fawning over celebs, and unfortunately the infamous Tom Cruise episode only underscored that perception. After railing about psychiatry, Cruise starts shouting about his love for girlfriend Katie Holmes (you can't quite make out what he's saying, but it sounds like, "Everybody gets a car! Everybody gets a car!"), then leaps up onto Oprah's couch doing the Snoopy dance and trying to play Twister with Oprah, who looks stunned but sort of adoring. Cruise's antics spawned one of the Web's best anarchic creative films. Special highlight: the "surprise" of bringing Holmes onstage, wearing that set-jaw grin and hopelessly caught-in-the-headlights look.

Video: Cruise Gone Wild
Video: Cruise Kills Oprah spoof

James Frey (2006): Fool me once, shame on you. Fool Oprah once, kiss your sorry-ass career goodbye. The author of "A Million Little Pieces" gets outed for embellishing and fabricating much of his memoir, after having it picked as an Oprah Book Club selection, which resulted in millions of sales. First Oprah defends him, but as the tide begins to turn, she does an about-face, calling Frey and publishing maven Nan Talese on the carpet. Special highlight: Oprah: "Well, James, what was it? One root canal, or two? I mean, that should be an easy enough question to answer." Frey goes grey-faced and looks a lot like Richard Nixon on the day he resigned.

Video: Oprah Confronts Frey 
Video: More Oprah vs. Frey 

Oprah at Large
David Letterman (1995-2005): Letterman will never live down his performance hosting the Oscars in 1995, almost as painful as James Frey's root canals. Vamping to fill time, he makes fun of attendees Uma Thurman and Oprah by pretending to introduce them, over and over and over again: "Uma, Oprah. Oprah, Uma." Hilarity did not ensue, and the incident fueled the feud between Oprah and Letterman (not helping: Letterman's ongoing, hilarious ridiculing of Dr. Phil, Oprah's protégé). They finally make kissy face in late 2005, when Oprah goes on Letterman's show to promote her new Broadway musical version of "The Color Purple." Special highlight: Oprah presents Letterman with an autographed photograph of ... Uma, Oprah.

Hermès Hoo-ha (2005): Oprah gets in a snit when the Paris luxury boutique won't open for her entourage for some after-hours shopping, which Oprah claims is due to racial reasons. Though many people think Oprah's arrogance showed in her expectations (can't you call ahead if you're a celebrity who wants to do a little after-hours shopping?), the retailer gets lightheaded thinking of the bad publicity and apologizes anyway. Special highlight: Oprah tries to portray a Paris shopkeeper as rude. Zut!

Not a Zulu (2006): PBS's riveting Black History Month series "African-American Lives" explores DNA testing to trace the ancestry of famous black Americans, including Quincy Jones and Chris Tucker. Oprah learns to her great consternation that her long-held belief that she was descended from Zulu warriors -- and hey, they conquered everyone, and so has she, so it's a mistake anyone could make -- isn't true. The look on her normally poised face is so affronted and real, it's priceless.

Oprah, Inc.: Yes, yes, we all know, she's one of the richest humans on the planet, with an estimated worth in 2005 of $1.3 billion (Hey, Oprah, everybody gets a car! Don't we?). In addition to the Oxygen TV network, books, DVDs, that "Live Your Best Life" magazine and the TV show that can't be stopped, she recently inked a deal with XM Satellite Radio to co-host a weekly "reality radio" show with longtime pal Gayle King, to debut in September 2006. Guess that makes her, if she already wasn't, Queen of All Media.

Faux Oprah (Fauxprah?)
"Saturday Night Live" Skits: You know you're an icon when "SNL" makes you a recurring character over the years. Our two favorites: Tim Meadows as Oprah in 1977 (interviewing Chris Kattan as Anne Heche), in which he appeared with minions carrying him like a goddess and was referred to as "The Oprah." And in 1998 Maya Rudolph (one of the best comedians on TV, in our humble opinion), skewered Oprah's two modes: serious concern for the downtrodden and fawning over celebs, by bringing onto her show a woman who'd lost everything in a fire. Oprah then says, "Well, Jane, this is your lucky day," and poor Jane, thinking Oprah's going to rebuild her house or at least give her a dang Pontiac, looks hopeful -- until her "surprise" appears: a visit from John Travolta, which makes the audience shriek in delight and Oprah suddenly becomes Celeb-Worshipper Oprah and utterly ignores the poor wretch sitting between them.

Kathy Griffin's Stand-up Shows: Griffin's shows on Bravo are endlessly quotable for the zingers she flings at celebrities. One riff that's priceless: describing Oprah's visit to the PBS series "Colonial House," in which she starts out as "cultured" Oprah, pontificating about how valuable public television is, and then as it dawns on her what the status of a black woman would actually be in colonial times, switching to "ghetto Oprah" and getting in the face of the show's producers. Wicked funny.

Dave Chappelle: If you had any doubts that he's one of the funniest dudes out there, wonder no more. Chappelle aired an extensive skit in which Oprah calls to tell him she's pregnant, and he instantly sees his life transformed. He quits his job, flames his employers and moves to Chicago to start burning through the Oprah fortune. His actual interactions with Oprah are few, but he does lovingly -- and territorially -- call her "my baby's momma" to whomever's handy, be it personal martial-arts teacher, masseuse, Diddy or, in an especially priceless bit, Steadman Graham.

Kati Johnston is a freelance writer who specializes in entertainment. E-mail her at kati.johnston@comcast.net.

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