From taking lunch orders for Taco Bell to greeting throngs of fans, Winfrey recalls her journey to success

By Sarah Durham Wilson
May 10, 2011 08:00 AM
Credit: Paul Natkin; Rob Howard

Oprah Winfrey is in a nostalgic mood these days.

The TV personality, whose illustrious 25-year run as host of The Oprah Winfrey Show is coming to an end in a matter of weeks, is looking back on her impressive career – with the help of her BFF Gayle King.

In the opening feature on the special celebratory June issue of O, The Oprah Magazine, King, 56, and Winfrey, 57, trace some of the milestones in the media mogul’s rise to the top, and only has the exclusive quotes.

The Moment Oprah Made It
King reminds Winfrey of pulling up to a speaking engagement 16 years ago in Racine, Wisc., where throngs of people waited eagerly outside.

“Oh, I remember that,” Winfrey recalls with a laugh. “We pull up to the place, the cops are lined up in double rows, and you go, ‘What’s happening here? Who’s here? Who’s here?’ And I go, ‘I am, you nitwit!’ ”

When Oprah Was the Host – and Waitress
“The first few years when the staff was still less than 12 people, I used to hang out with them because we were doing live shows, and we’d be done by 10 a.m.,” says Winfrey. “We had four people in four chairs, and that was it. Those were the days where I’d be the one taking the lunch order. I would walk around asking, ‘Okay, is it gonna be Taco Bell today, or are we doing Wendy’s?’ ”

Saying Goodbye to Her Loyal Audience
“I genuinely feel appreciated and loved by this audience that has grown up with me. Which, for me, is a huge, huge, huge accomplishment. Because I grew up feeling the opposite of that,” says Winfrey. “When you see [my] tears on the last show, that’s what those tears will be about. Those tears will not be about sadness.”

Her Surprise Final Guest
“It speaks to the essence of what the show has tried to say all these years: that you are not the product of your circumstances,” says Winfrey who will not reveal the identity of the guest on the last episode of her show. “You can step out of your history and create a new day for yourself. Even if the entire culture is saying, You can t. Even if every single possible bad thing that can happen to you does. You can keep going forward.

The complete story is in the June issue of O, on newsstands May 17.