Paolo's TV Debut
One of Oprah's favorite wildest dreamers was Paolo, an Illinois man who worked at his family's grocery store but desperately wanted to become an actor. He turned to the one person he knew could help make his dream come true: Oprah. And she delivered—Paolo got offered a speaking role on the hit sitcom Will & Grace!

After his primetime debut, Paolo moved to Los Angeles to pursue his passion and landed a role on General Hospital. What was supposed to be a one-time appearance became a recurring role!
Rosie Rodriguez and Barry Manilow

Barry Manilow's Biggest Fan
Rosie Rodriguez, a lifelong Barry Manilow fan, never saw it coming. In 2004, she went to a Chicago restaurant to tell Oprah Show producers why she's Barry's biggest fan. In the midst of her phony interview, she mentioned her favorite song, "Can't Smile Without You."

Without missing a beat, Barry sneaked in behind Rosie and began playing his hit on the restaurant's piano. "Oh my God," Rosie said. "This is so him!"

After that show, Rosie attended her first Barry Manilow concert in Las Vegas—a dream come true!

Smile Makeover
Since Rachel was a child, she said she'd lived with embarrassment and shame.

"I have always hated my teeth and what they look like," she said. "Some people might not even know my teeth are so bad because I've covered them up so much. If it's a big laugh, [I] always hide it."

This stay-at-home mom has four children, including 3-year-old Jacob, who has autism. Instead of fixing her teeth, Rachel always put her family's needs above her own.

For one day, Oprah wanted Rachel to be the priority, so she sent Rachel to New York to meet with Dr. Marc Lowenberg for a smile makeover. Look at those pearly whites now!
Gayle King and Josh Groban

A Secret Serenade
To make one workday a day to remember for her best friend Gayle, editor-at-large of O, The Oprah Magazine, Oprah got in touch someone special—Josh Groban.

Josh, Gayle's all-time favorite singer, was sent to her office to do a special serenade. Minutes before he was set to arrive, Gayle called Oprah to talk about—who else?—Josh Groban! "His voice does something to me," Gayle said. "I just feel him!"

While Gayle sang some of her favorite lyrics into the phone, Josh walked into her office holding a bouquet of yellow roses. "Oh my goodness!" she screamed. "Josh is here!"

Gayle followed Josh into a conference room, which had been transformed into a romantic concert hall. As magazine staffers gathered around, Josh got down on one knee and serenaded Gayle with the song she'd just been singing on the phone, "When You Say You Love Me," from his album Closer.
Ms. Quinney's class at Disneyland

I'm Going to Disneyland!
When elementary school physical education teacher Ms. Quinney wrote to The Oprah Winfrey Show about her wildest dream, we put in a special request—with a mouse.

"The thing I've always wanted to do most was take my students to Disneyland," Ms. Quinney said.

Most of Ms. Quinney's students at Crockett Elementary don't get the chance to experience life outside of their inner city neighborhood in Houston. For once, she said she wanted to give her students an opportunity to be childlike. "Just one day away to do something that they really, really like would help them to forget about all the sadness that's going on in their little lives," she said. "They're worried about problems that grown-ups have, and kids shouldn't have to go through that. They should enjoy being young and carefree, but they're not."

After Ms. Quinney and her students took a jet to California, their fun-filled day began with a trip to Sleeping Beauty's castle and a visit from Mickey. Oprah and the children took some teacups out for a spin, flew with Dumbo, and ended the day with the Parade of Dreams. 

"Today's the most fun I ever had in my entire life," one student said.
Felicity Huffman

Backing Up the Best
When Oprah found out that Desperate Housewives star Felicity Huffman dreamed of being a backup singer, the Wildest Dreams machine went to work! After all, Oprah had some experience backing up the best, so she knew exactly who to call: the one and only Tina Turner.

Singing backup to Tina's "You Better Be Good to Me," Felicity had the time of her life. "It felt like a racecar," Felicity said. "It was like great sex!"
Jake and Stevie Wonder

Sharing the Spotlight with Stevie Wonder
One of Stevie Wonder's biggest fans got the surprise of a lifetime during our Wildest Dreams season. Jake Simpson, a Star Search grand champion, came on the show to talk about his big win. Little did he know, his music idol was waiting in the wings.

As Jake began to perform, the curtains parted to reveal Stevie, leaving Jake shocked and speechless—but not breathless. Sharing the spotlight, the two sang "Isn't She Lovely" together.

Jake, who's still making records, said that was the most amazing day of his life.
Jay-Z with the Canterbury Boys High School

For the Love of Hip-Hop
In 2010, Polly Dunning wrote to The Oprah Show about her students at the Canterbury Boys High School in Sydney, Australia. "The boys come from a variety of cultures and nationalities with 90 percent from a non-English speaking background. Although they are all different, we all love hip-hop music, including Jay-Z," she wrote. "Jay-Z has let my students see that you can come from the bottom and reach the top."

While Oprah was in Australia, she arranged for Jay-Z to make a surprise appearance at the school.

Not only did the boys get to meet the hip-hop mogul, Microsoft Australia and their partner HP hooked them up. "Every single student is taking home an HP DV7, top-of-the-line powerhouse laptop, and they are giving every single teacher their very own laptop with Microsoft Office," Oprah said.

In addition, HP and Microsoft made over the school's library with 15 TouchSmart 600 computers and HP Envy Beat notebooks for the music rooms. "Now [there's] no excuses not to do your homework," Oprah said to the students.

A Singer Teams Up with Mariah Carey
Mariah Carey joined Oprah's Wildest Dream Team to surprise a very special boy from Hawaii. It all started with a letter from 12-year-old Paul whose biggest wish was to sing on Oprah's stage. So Oprah's team met Paul and his parents outside their home in Hawaii with the exciting news: Paul's wildest dream was going to come true!

First, Paul made a pit stop in Los Angeles, where he met Mariah and American Idol's Randy Jackson. After Mariah and Randy coached Paul on some vocal basics, it was time for his worldwide television debut.

Paul blew the audience away with his rendition of Mariah's number one hit "Hero." But Paul's whirlwind dream wasn't over just yet. Verity Records offered Paul a contract to record a song called "I Pray" —written just for him by Mariah!
John and Derek Jeter

A Day with Derek Jeter
Like many young boys, John grew up with a love for the outdoors and a passion for sports, including baseball, basketball and football. But, in the summer of 2004, after John developed mononucleosis, a common viral infection, his parents noticed something was wrong. Within hours of taking him to the hospital, doctors discovered that an extremely rare form of muscle-eating bacteria was ravaging John's 17-year-old body. To keep the disease from spreading, doctors amputated his legs and part of his arm.

This amazing teen's family, friends—even complete strangers—wrote in to tell Oprah about John's courage and the one big passion that keeps him going: the New York Yankees.

The Wildest Dreams team planned a pep rally at John's school, with a special surprise guest:New York Yankees shortstop Derek Jeter! Derek took John to the exclusive Yankee clubhouse and let him warm up on the field with the team.

But, of course, that wasn't all—to help pay for John's medical expenses and his prosthetic legs, Kleenex brand tissue gave John a check for $50,000. Plus, when we heard that John's parents, John Sr. and Barbara, were forced to cancel their 25th wedding anniversary because of the medical costs, Royal Caribbean Cruise Line agreed to send them—and their children and 10 closest friends—on an all expenses-paid, seven-night, luxury cruise!
Denni and her family

Help for a Hardworking Mom
Denni, a single mom of three children, was working three jobs to give her children the education they needed to succeed. With her hard-earned paychecks, she was able to put all three of her children through college, but she incurred $78,000 in student loans along the way.

Denni's son, Johnathan, wrote to Oprah to tell her about his hardworking mom. Denni's dream was to one day go to Italy, so Oprah surprised Denni and her children with a luxury dream vacation to Italy!

Still, there was a big burden hanging over Denni's head. At the rate she was working, she'd "be a young 93" by the time she paid off her children's student loans. "Well, it will not take you that long," Oprah said. "Because we're going to pay off all those loans!"

Before that day, Denni said she thought her life was over. "No, no," Oprah said. "Your life isn't over. It's just beginning."

Bernadette's New Home
Bernadette, a hardworking single mother, took custody of her six nieces and nephews after her brother and his wife became addicted to heroin. Along with her own three children, the family of 10 was crammed into her three-bedroom apartment. "I'm happy that we're all together, but it just makes me feel sad that I can't do better to accommodate them," Bernadette told Oprah. "I think last Christmas was the worst Christmas of my life because three of my children had to wake up with nothing."

Bernadette's wildest dream was to celebrate a beautiful Christmas with her family. And Oprah delivered—the kids went crazy on an all-you-can-grab shopping spree at Toys"R"Us!

But where would they store all of their new toys? Oprah hired her Realtor®, Ameta Cartwright, to help Bernadette choose a brand new house! For the first time in her life, Bernadette became a homeowner. She picked out the perfect house, a 1920s brick bungalow with enough space for the whole family.

To make her house a home, Nate Berkus gave Bernadette a home makeover, complete with a brand new kitchen and beautiful furniture.
Britney and Bethany

Double the Surprise
Growing up, identical twins Britney and Bethany had to overcome challenging learning disorders that severely delayed basic speech development. Against the odds, they accomplished the seemingly impossible—they not only finished high school, but graduated at the top of their class.

Britney and Bethany were accepted into the school of their dreams, Baylor University in Texas, and the whole family pitched in to try to help. The twins' siblings secretly worked extra shifts and saved $10,000. The family even considered selling their house in order to pay for Britney and Bethany's college education.

To help fulfill their wildest dreams, Oprah sent American Idol star Clay Aiken to surprise Britney and Bethany. He told the twins that they were heading to Chicago for an episode of The Oprah Winfrey Show they'd never forget.

When Britney and Bethany arrived for the show, Ty Pennington of Extreme Makeover: Home Edition, announced that he would outfit each sister's college dorm room with his home line from Sears!

And, of course, that wasn't all. "Britney and Bethany, your tuition is paid!" Oprah said. "Your room and board is paid! Four years at Baylor—completely paid!"
Monica Jorge

A House for a Warrior Mom
Monica Jorge, a warrior mom who had her arms and legs amputated after contracting a rare flesh-eating bacteria, is one guest Oprah never forgot. Although her life was turned upside down, this inspirational mother never lost sight of what was most important to her: family.

When Oprah learned that Monica was facing more hardship, she stepped in to make another dream come true. In 2010, Monica's husband Tony lost his job as a maintenance mechanic, and the family's living situation was far from ideal. Their modest rental apartment wasn't designed for a person with physical disabilities, so Monica relied on Tony and her two daughters, 12-year-old Madeline and 3-year-old Sofia, to complete everyday tasks like loading the dishwasher and cooking dinner.

Oprah teamed up with Nate Berkus to give Monica's family a life-changing surprise. "No more renting," Oprah said in September 2010. "No more teeny tiny apartment. No more little bitty bathtub. No more cabinets that you cannot open and using your 3-year-old to help you...because we are buying you your very first home!"
Oprah's car giveaway

Car Giveaway
Oprah kicked off her 19th season with a premiere so big, we needed two EMTs on hand in case things got a little too wild. "I'm so excited about today's season premiere, my heart is palpitating!" Oprah said. "I'm going to try not to faint!"

The wildest dreams of an entire audience came true: Each person was given the keys to a brand new 2005 Pontiac® G6™!

"You get a car! You get a car! You get a car! Everybody gets a car!" Oprah said.

Watch one of the biggest surprises in Oprah Show history Watch