Oprah's Blackest Moments

Oprah Winfrey recently announced plans for retirement in 2011. The talk show host may have a stronghold on white, suburban housewives, but The Root contributors remember moments when Oprah kept it real—black.

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I've never known a world without Oprah on TV. I'm 24, and her show is 25. I didn't watch Oprah much growing up, but I do remember watching Kim Wayans on In Living Color and Debra Wilson on Mad TV, always making jokes of her weight, her tearful episodes and her suspected attitude problem. And don't forget the episode of Fresh Prince of Bel-Air, when Oprah invited the Banks family—sans Will—to the show. Those are some of the funniest Oprah moments—and she wasn't even there.

—Erin Evans, copy editor for The Root

It was big when Oprah gave away free cars to everyone in her studio audience, but it was even bigger when she gave away Kentucky Fried Chicken grilled chicken to thousands of hungry people. After a grilled-chicken promotion coupon was posted on Oprah.com, there were feathers flying everywhere. Fights and even riots broke out in KFCs across the nation when it turned out there was not enough chicken for everybody.

—Eboni Farmer, intern and writer for The Root

I thought nothing could beat the folly of Beyoncé showing Oprah how to gyrate to “Bootylicious.” But, then I watched Jay-Z’s cipher with Oprah this September and realized if this wasn’t one of her most overdue black moments, it definitely was one of her most memorable ones. While I gained rare insight into Jay-Z’s editing and freestyle rapping, his spitfire precision and mid-phrase self-correction, I couldn’t help but chuckle at Oprah’s earnest attempt to repeat the most basic of Jigga’s verses: Little boy from Brooklyn, made it from the ‘Stuy/girl from out the South made it to the ‘Chi/Only goes to show that the limit is the sky/if life give you lemons then you make lemon pie. Yes, in this episode of the African-American Horatio Alger story, of black mogul to mogul love, Oprah was too eager, too unfamiliar with the basic rhyme pattern, and pointed her finger too much as she was rhyming. But, there was also something else at play here, for Oprah, patiently guided by Jay-Z and cheered on by both the simple DJ beat and the bobbing heads of her audience, reached her arms out to the hip-hop generation, and finally, if only for a moment, and I mean close to a nanosecond, rocked the mic.

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