Oprah says she'll never forget her first job. As a teenager growing up in Nashville, Oprah began working at the corner grocery store next to her father's barber shop...and she hated it every minute of it.
"I wasn't allowed to talk to the customers, and can you imagine for me?" she says. "That was very, very, very hard."
Then, at 16, she landed a job that paid her to talk. A Nashville radio station, WVOL, hired Oprah to read the news on the air, which she says she loved.
This gig helped Oprah get her big break. In 1973, Oprah was a 19-year-old sophomore in college when she got a call that changed her life. "I remember leaving class to go take a phone call from Channel 5's Chris Clark," she says.
Chris, a television news reporter, says he remembers Oprah as a well-spoken, poised young woman. When she came in for an interview, Chris says he asked her two questions: "Can you run a camera, and can you write a news story?"
"I think I lied and said, 'Sure I can,'" Oprah says.
Well, it wasn't long before Chris realized she could do neither, but by then, he'd seen her come alive on camera. "What you see in Oprah today is what I saw so many years ago," he says. "Oprah, you had the magic to communicate on television, and that is natural born. You just can't learn that. You can't develop that. You got it or you don't got it."
The first time Oprah was on television, she says it felt like the most natural thing in the world. "It just felt like breathing," she says. "It felt like this is where I'm supposed to be."
Chris, Oprah's first television boss, joins her via Skype to reminisce about their nightly newscasts. What Chris remembers most about Oprah are her eyelash mishaps.
In an attempt to look a little more like her '70s idol, Mary Tyler Moore, Oprah says she tied scarves around her neck and wore false eyelashes that she bought at Walgreens—the same brand she still wears today!
"I didn't know how to put them on very well," she says. "By the end of the newscast, my eyelash would be falling off."
"In a half-hour newscast, I think people were tuning in to see where [the eyelashes] were after the commercial break," Chris says.
Truthfully, Oprah says eyelashes weren't her only problem. "I wasn't a really good reporter," she says. "As a reporter, you're not supposed to empathize with the people that you're reporting on, and it's very difficult to be writing copy when somebody's been in an accident."
When Chris assigned Oprah stories that involved people who were hurt, he says she'd be too distraught to write the copy. "She spent all of her time on the telephone trying to find help for these people instead of writing the darned story to meet the deadline," he says. "It probably was very good she never got the message. Look at her today. I mean, come on. She has empathy for people. She wouldn't be Oprah without that."
While Oprah was in Dallas filming a show at the annual state fair, she did something she hasn't done in 26 years: a live newscast!
"I thought, 'Well, as long as I'm stopping by our affiliate, WFAA, in Dallas, why not see if they'll let me take my old job back for just a moment?'" she says. "So I gave it a shot."
Oprah shared the anchor desk with Gloria Campos, a TV news legend in Dallas. "I'm a little nervous because she is such a good talker," Gloria says. "Time might get away from us."
As the clock ticked closer to 5 p.m., Oprah says she started to get nervous. "My anxiety dream is always I'm sitting at a news desk with Walter Cronkite and all my papers are confused," she says.
But, as soon as the teleprompter started to roll, it all came back to her.
"It feels rather natural," she says. "Kind of like riding a bike after a long time."
Long before she was a famous movie and television actress, Kirstie Alley identified with an unlikely female lead—Cinderella.
As a 16-year-old in Wichita, Kansas, Kirstie entered into the workforce as a housekeeper. A childhood friend's mother, Anne Kathol, hired Kirstie to clean their house and taught her lessons she still carries with her today.
"Mrs. Kathol said: 'Put your back into it. You got to put a little pressure. It's not going to clean itself,'" Kirstie says. "She made me feel very validated. ... And she gave me the work ethic."
To this day, Kirstie says she can still make a sink sparkle. In the bathroom, her favorite room to clean, Kirstie uses a special cleaning solution: vodka.
"You buy the cheapest vodka in the universe in big gallons, but it doesn't work if you have a housekeeper who's an alcoholic," she jokes. "Vodka is antibacterial, and it's not toxic and it doesn't have any scent. ... It actually makes things really shiny and really clean, and it's actually cheaper than cleaning products. I've used it for 20 years."
After learning to clean houses, Kirstie graduated to decorating them.
Just a few years before landing a role on one of the most poplar shows in television history, Cheers, Kirstie got her first adult job at Dean's Designs, a Wichita interior design firm.
Kirstie says she still doesn't know why Dean White, the store's owner, hired her. "I should have been fired for real. I was doing cocaine," she says. "He gave me the troublesome clients—we were a good match."
One day, while doing work for a client, Kirstie says she decided to make some extra money by putting up the wallpaper herself. "So my friend and I hung it over vinyl," she says. "It's about 6 o'clock at night, and all of a sudden, the wallpaper starts [peeling off] and just from every corner, it started folding in on us. And he still didn't fire me."
Kirstie says she stopped doing drugs in 1979. "I only did drugs for a couple of years," she says. "But I did my share...and yours."
Kirstie's latest job was inspired by a pledge she made the last time she was on The Oprah Show.
Well, that didn't happen...but Kirstie says there's a good reason. "I decided: 'You know what? I need a show that shows the journey of losing weight,'" she says. "Because losing weight isn't about, 'Here's your before picture, and here's your after picture.'"
After she left Chicago, she got in contact with a production company and began pitching the show to networks. "I'd lost about 20 pounds, and they said, 'Put the brakes on, because this is what we're paying for—to see you lose this weight,'" she says.
Kirstie says her first network deal fell through, but now, she has a contract signed, sealed and delivered. "Do you know when we closed this deal on the show? Midnight last night," she says. "I'm not lying."
The concept of Kirstie's "docu-reality" A&E series, Kirstie Alley's Big Life, is the making of a misguided mogul. Her children, Lillie and True, are also part of the cast. "I'm shooting from wherever I am. I'm going to have a videographer in my house basically every single day," she says. "I created the show, and I want it to be a real journey. I want it to be what really happens to you, inside and out."
Long before she became one of the most influential money experts in America, Suze Orman worked in what she calls an even tougher business—the food service industry. From 1973 to 1980, Suze was a short-order cook and waitress at the Buttercup Bakery in Berkeley, California.
Suze says she loved being the first person many customers saw every morning. "They couldn't wait to come in, see the regulars, have their cup of coffee, say hi to me, sit down. It was like a family," she says. "I felt like I belonged somewhere back then."
Since Buttercup Bakery is now a sushi bar, Suze spent the day at Olympia Flame Diner in Deerfield Beach, Florida, reliving her glory days behind the griddle.
After a few hours of flipping pancakes and scrambling eggs, Suze says she missed it more than ever. "It makes me kind of want to do this again," she says. "I actually want to go back and have what's called 'Suze's Sunday.'"
Suze also put on a dress for the first time in decades to see if she still has what it takes to make it as a diner waitress. While working at Buttercup, Suze says she learned that who you are has nothing to do with what you do.
"Who you are is how you treat people, how you serve people, how you cater to them," she says. "I learned if you could just be kind to people, if you could just be pleasant to people, that the greatest tip in life is when they smile back at you."
Waitressing also helped Suze discover the key to happiness. "I learned that when you make average great, your dreams can become a reality," she says.
Before they were famous, many celebrities—including Shania Twain, Madonna and Jay Leno—worked behind the counter at fast food joints. For the first time in more than 20 years, country star Martina McBride made a stop in Hutchinson, Kansas, to revisit the Dairy Queen where she once worked.
"I moved here to go to school, to sing in a band, and I had to pay my own bills," she says. "I wanted to make my own way."
At the time, this Dairy Queen was owned by Wilbur and Vera Graber...and it still is! This couple has served up soft serve for than 40 years, and Wilbur still remembers hiring Martina back in 1984.
"She was one of the best," he says. "And she was always willing to learn."
With a cone in hand, Martina can still create the classic Dairy Queen curl, but that's not all she learned during her time here. "I think that I carry with me from this job just a way to treat people. I know that when I go in a restaurant, I completely empathize with the person working behind the counter," she says. "I think just having that experience really gives you a great perspective."