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Talk show titan Oprah Winfrey has sported many hairstyles over her 25 year career—from feathered bobs to shaggy chops—and gone modern minimalist to super glamorous in her makeup. "I carry more than a thousand lipsticks to her photo shoots and shows because she always wants a new color," said her longtime makeup artist Reggie Wells, who has used everything from burgundy to tangerine on Winfrey's pout. But her mouth isn't doing all the work. "She has the most expressive eyes," Wells noted. "They also speak volumes." And despite the fact that she has retired from her show, Oprah shows no signs of slowing down. As Wells has said, "She's still full of energy and inspires everyone around her." A peace-loving Winfrey (and her perfect flip) graduated from East Nashville High School with a full scholarship to Tennessee State University. (CREDIT: Yearbook Archives) See the Full Story
As the up-and-coming host of "A.M. Chicago," Winfrey sported bronze shadow up to her eyebrows and some seriously big bangs. (CREDIT: Photofest/Retna) See the Full Story
After lighthearted contributions to "The Princess and the Frog" and "30 Rock," the talk show titan tearfully announced that she will be ending her program in 2011: "Twenty-five years [onscreen] feels right in my bones and feels right in my spirit." (CREDIT: Jeffrey Mayer/WireImage) See the Full Story
