Oprah’s Dream Season and ‘You Get a Car’ Moment Was 20 Years Ago (Exclusive)

It was a moment that spawned a million memes — but also changed lives in a meaningful way.

Oprah Winfrey‘s “Wildest Dreams” season aired 20 years ago in 2004, and along with the memorable “You get a car!” moment, included heartfelt fan interactions that led to some truly special outcomes for the people featured.

One such fan is Paolo Presta, who was busy working at his family’s grocery store outside of Chicago when Winfrey and her team popped in to gift the aspiring actor a walk-on speaking role on Will & Grace.

“I was just changing labels on the pasta, and remember someone calling my name,” Presta tells PEOPLE exclusively. “And when I got up, I saw her. I didn’t know what she was there for — even though I wrote her so many letters and emails, I imagined they went in the garbage. But I knew whatever she was there for was going to be something good.”

A lifelong fan, Presta often attended tapings of The Oprah Winfrey Show in Chicago.

“Something about being there felt like a safe space for me,” he recalls. “And I remember I went to one taping — it was Jennifer Lopez and Richard Gere for their movie, Shall We Dance? — and I was telling my friend, ‘Just wait: one day Oprah is going to interview me.’ I just always felt there was something more to my life, I just didn’t know what it was.”

The son of an Italian immigrant and one of seven siblings, he’d worked for his parents since his tween years, dreaming of something bigger. So once Winfrey approached him at the grocery store, Presta’s “excitement all just came out,” he recalls. “That one moment was the start of a new life for me.”

At the time, Presta wasn’t yet out to his Catholic Italian family. “I was hiding that, which really sets you back,” he shares. “So that moment was the beginning; being able to come out to my family changed my life.”

Soon after he moved to Los Angeles to shoot his Will & Grace episode and work in television, looking to feel like “his authentic self,” he says. “And it brought me to where I am today.”

Presta remembers walking onto the Will & Grace set, another show he calls a “safe space” for him.

“It was the most magical time,” he says of sharing the screen with Eric McCormack, Debra Messing, Sean Hayes and Megan Mullally. “I got to be with the actors who literally have helped me become who I am today.”

It also helped Presta realize who exactly he wanted to be: himself, not an actor playing someone else.

“Oprah was herself, interviewing people. From there, I learned after a few months in Los Angeles that what I really wanted to be doing was working on a daytime talk show.”

After experiences on The Ellen DeGeneres Show and The Talk — and following the launch of his own Q&A show, A Spoonful of Paolo — Presta and his husband Patrick Thomassie moved back to Chicago in 2017. And in 2024, life came full-circle when he reached back out to Winfrey and brought her to his show, in an episode set to air on Nov. 11, the anniversary of the day she surprised him in 2004. (The two have remained in touch, with Presta helping present Winfrey with her Vanguard Award at the GLAAD Media Awards earlier this year.)

“It felt so good to tell her how much I appreciate her,” he shares. “In the beginning of the interview I say, ‘You’re my friend, you’re my angel, you are my favorite teacher.’ The episode really is a thank-you letter to her.”

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Looking back on that fateful day in 2004, “I still get goosebumps,” Presta shares. “It hits you in the heart. I know what I’ve been through in my life. I carried what Oprah did for me and I made it go further. I took it and I ran with it, and I just wanted to keep going because I knew that when you dream big and you are your authentic self, the door is open and so many things are going to come your way if you keep doing the work.”

Reflecting on Winfrey’s lasting legacy, what stands out to Presta is her ability to inspire.

“When you bring people so much joy when they’re watching in their homes, it just motivates people to keep dreaming big and always believe in themselves no matter what the obstacle is, no matter what your background is,” he says. “To believe in yourself, and fight for your dreams.”