20 & O!
THE FIRST SHOW
After unsuccessfully trying to line up a celebrity for her first national show, Winfrey instead focused it on "how to marry the man or woman of your choice." But she made her own star power. Within a year, she had the nation's top syndicated talk show. "I don't know another overweight Jheri-curled person who can say, M made it!' " she says on the just-released DVD of the show's first 20 years. (Proceeds will benefit Oprah's Angel Network.) More Oprah history can be seen on the show's Nov. 22 anniversary episode.
THE FAT WAGON
On a liquid diet for four months, Oprah went from 212 lbs. to 145 and wheeled 67 lbs. of fat on to the stage to show the difference. Two days later, the size-10 jeans were already too tight. "Today, it's probably her biggest regret because it was so drastic and ultimately it didn't work for her," says her best friend Gayle King. "It's only when you're older and wiser that you think, 'Why did I do that?' "
THE BOOK CLUB
Jacquelyn Mitchard's The Deep End of the Ocean was named as Oprah's first pick and the novel sold 900,000 copies in the month after the show. Since then, the "Oprah Effect," as publishers call it, has graced 53 more books and prompted the creation of other book clubs across the country. Says Mitchard: "It gave everyone permission to love good writing."
DANCING WITH TINA TURNER
"I don't think I've ever been more nervous," Winfrey said of appearing onstage with Turner on her Wildest Dreams tour. "My knees were knocking." The same year, Winfrey started her Wildest Dreams program, granting the wishes of dozens of viewers who wrote in with requests for everything from a new home to a camel ride.
Born with a rare form of muscular dystrophy, Stepanek brought Oprah viewers to tears with his hope-filled poetry. His Heartsongs was soon a bestseller, and Mattie appeared on the show several more times before his death at age 13 in 2004. "It was his dying wish to make a difference that would last longer than his body," says his mother, Jeni Stepanek. "And Oprah gave him the gift of opportunity."
VISITING SOUTH AFRICA
Over the course of three weeks, Winfrey helped 50,000 children by delivering clothes, toys and many hugs for Christmas. "One of the most poignant moments for her was after she delivered gifts to one location, one little boy said, 'Oprah, go well,' " says King. "Clearly she is much more than a talk show host, and being there crystallized that for her."
THE CAR GIVEAWAY
Winfrey kicked off her 19th season by giving a Pontiac G6, donated by the manufacturer, to everyone in her audience. All 276 of the recipients had been handpicked by her staff because they were in need. "It didn't sink in until we all ran out to see the cars," says Becky Thomas of Waukesha, Wis., whose son's medical bills didn't allow the family to afford a new car. "She enjoys more than anything giving and sharing," says King. "Nothing makes her happier." That would explain Winfrey's annual "Favorite Things" episode, airing Nov. 21.
THE BIRTHDAY SHOW
It was Oprah's turn to be surprised when stars like Stevie Wonder, John Travolta, Gayle King and Tina Turner showed up to wish her a happy 50th. "She had no idea," says Jay Leno, who wheeled out a 400-lb. banana cake. Adds pal King: "There aren't a lot of us who 20 years later look better. But she does. She looks better, she feels better, she is better."
TOM ON THE COUCH
After punctuating his declaration of love for Katie Holmes with a bounce on the couch on May 23, Tom Cruise didn't offer to clean the sofa, Winfrey said in O. "And aren't I glad. Now we can auction it for the Angel Network and make a lot of money."