In 2004 Oprah crashed like a magnanimous meteor into the lives of thousands — most spectacularly with her declaration of “You get a car! You get a car! You get a car!” as stunned guests opened little boxes wrapped in red ribbon to find the keys to a new Pontiac.
Audience members had gotten free stuff before, notably on the Thanksgiving week “Favorite Things” giveaways, but nothing like that.
The date was Sept. 13. It was the premiere episode of her 19th year as a talk show host. She dubbed it her “Wildest Dreams” season.
The theme was emblazoned on the side of a bus that served as the daytime talk show queen’s Santa sleigh, taking her team from city to city, wherever a fan needed help.
It marked a new level of largesse, and ratings.
We checked in with a few people whose lives were touched.
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Paolo Presta was pricing bags of pasta at his family’s grocery store in Hoffman Estates when Oprah’s bus stopped outside — cameras rolling.
It was Nov. 11, 2004.
Presta, who was 28 at the time, had written to Oprah dozens of times asking for help fulfilling his dream of becoming an actor and overcoming the gravitational pull of his father, who grew up on a farm in a small town in Italy and just didn’t understand why his son would pass on a steady paycheck working in the family business.
Oprah stepped off her bus and announced that Presta would be going to Los Angeles to act in a role she’d secured for him on the hit sitcom “Will & Grace.”
It was a momentous declaration. Oprah was a staple in his family’s home.
After his brief bit on the sitcom, Presta later acted on “General Hospital” and worked behind the scenes on daytime talk shows, including “The Ellen DeGeneres Show.”
In 2011, along with his husband, he launched an online talk show called “A Spoonful of Paolo” in which Presta interviews people in the entertainment business.
Guests have included Brooke Shields, Gayle King, Kris Jenner, Carol Burnett, Julie Andrews and Whoopi Goldberg.
“What Oprah did, it changed my life, honestly, it gave me the courage to move to L.A. and pursue my dream,” said Presta.
In a full-circle moment, Presta interviewed Winfrey for an episode of his show that went online Nov. 11.
“You see the heart, the love,” said Presta, who moved back to Chicago in 2022 to be near his mother, who has since passed.
“My dad’s still alive, and both my parents always told me how proud they were of me.”
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Before visiting Presta, Oprah’s bus stopped by a Northwest Side coffee shop.
Before placing her order, she had something special for one of the baristas, who was a single mother caring for not only her own three kids, but also her mother and seven nieces and nephews.
Oprah gifted her a new home and offered to personally fund the college education of each child who strove for it.
Two decades later, the woman still works at the same coffee shop. She declined to speak to the Sun-Times about her life since then.
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If William Toebe looked down while he was driving back in 2004, he could see the roadway through a hole in the floorboards of his dilapidated Chrysler LeBaron. If he looked up he saw another one in the convertible’s rooftop.
In hopes of being selected to be in the audience of Oprah’s show and getting some sort of car-related financial assistance, Toebe’s wife, Jillaine, plopped their young kids on the hood of the beater, took some photos and sent the, too Winfrey.
It worked. A producer from Oprah’s show called Jillaine, told her how cute her tiny daughter’s chubby thighs were, and invited the couple to be on the show. They made the four-hour trek from their home near Green Bay, Wisconsin, and were among the 276 people in the audience who got a new Pontiac G6.
The couple sat in the cars one time before selling them both back to the dealership for $46,000. They ended up collectively bringing home $32,000 because — even though the cars were free — audience members were still on the hook for a portion of the taxes.
It was still $32,000.
“We had little kids, it gave us a little breathing room, a head start,” said Toebe, who works in home health care. “We were able to pay off the highest-interest credit card bills.”
The couple also used a portion of the money to buy a used car.
“It certainly was a positive event in our life,” he said.
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Sonya James was in the audience when Oprah shouted, “You get a car!”
It changed her life. Not because of the car — though it did prove to be a great ride for two years until a drunk driver totaled it while it was parked in front of a friend’s house.
“It just changed my whole mindset with respect to giving,” she said. “For some reason I thought you had to be wealthy to be a philanthropist, but I realized that wasn’t true.”
James started to raise funds through small community gatherings and used the money to help people — could be a few hundred dollars to pay a utility bill or buy a microwave oven, or a few thousand to cover college tuition.
It was all an unofficial word-of-mouth endeavor at first. She later formed a non-profit and named it after her father, Jerry Hawkins, a Chicago police officer who died of congestive heart failure at 51. She ran the organization for several years with the help of her mother, Julia Hawkins, who for years taught in the Chicago Public Schools.
Ellen DeGeneres got word of what James was doing, had her on her own daytime talk show and gave her $25,000.
James now lives in Arizona and works for the Social Security Administration. Her charity hasn’t been active for a few years, but she’s trying to start a new one to help give young people positive ways to spend their time.”I remember every detail of being on that show. It was my fourth time being on the show, and it was a real turning point in my life,” she said.