24 Moments from Oprah's Season 24 Kickoff Party

Setting up for Oprah's Season 24 Kickoff Party

To celebrate her 24th season premiere, Oprah took over Chicago's famed Michigan Avenue for a fun-filled, star-studded event! Before thousands of fans filled the streets, crews worked overtime to get the stage and lighting assembled.

Crowds gather for Oprah's Season 24 Kickoff Party.

As the 5 p.m. showtime neared, more than 21,000 people gathered on Michigan Avenue to see performances by the Black Eyed Peas, magician Criss Angel, Jennifer Hudson, James Taylor and Rascal Flatts.

The men and women of Oprah's production crew who helped make the kickoff party possible gathered in front of the stage before the show.

Fans show off homemade signs at Oprah's Season 24 Kickoff Party.

Many spectators traveled great distances for a chance to see a history-making episode of The Oprah Show.

Dancers teach the audience members choreographed steps.

Before the show began, trained dancers taught audience members choreographed steps. When the Black Eyed Peas kicked off the party with their song, "Oprah Feelin'," the dance spread through the crowd, much to Oprah's surprise!

To pull off this flash mob, producers brought in the creative masterminds behind the T-Mobile viral sensation, award-winning director Michael Gracey and choreographer Ashley Wallen.

Goodyear Blimp at Oprah's Season 24 Kickoff Party

High above the Chicago skyline, the Goodyear Blimp invited everyone in the city to Oprah's party!

Before the show, Extra correspondent Mario Lopez interviewed Oprah atop a red double-decker bus.

Oprah opened the show with a shout out to Chicago! "Isn't this the most fabulous city in the world?" she said.

Even four-legged fans got in the spirit at Oprah's Season 24 Kickoff Party!

Fergie and will.i.am sing "Oprah Feelin'".

As the first performance of the evening, three-time Grammy-winning group the Black Eyed Peas sang "Oprah Feelin'," a new mix of their smash hit "I Gotta Feelin'." The Black Eyed Peas wrote this version of the song just for Oprah!

Dancers at Oprah's Season 24 Kickoff Party

As the Black Eyed Peas sang "Oprah Feelin'," the audience performed their choreographed dance number—a history-making moment! As the music faded, thousands stood together with one finger held in the air.

Fergie, will.i.am and Oprah celebrate in Chicago.

Once the flash mob dance ended, Oprah, Fergie and will.i.am gave the audience their due. "That was the coolest!" Oprah said. "Woo, that was fun."

The Black Eyed Peas—Taboo, apl.de.ap, Fergie and will.i.am—sat down with Oprah to talk about weddings, babies and future projects.

Five days before Oprah's Season 24 Kickoff Party, illusionist Criss Angel made three predictions, wrote them on a piece of paper and locked them inside a metal box. An audience member unlocked the box to prevent Criss from tampering with the contents.

Watch Criss Angel's trick unfold.

As Criss revealed the words he wrote, Oprah stood by in shock.

Go backstage with Criss.

Jennifer Hudson performs at Oprah's Season 24 Kickoff Party.

Chicago's own Jennifer Hudson got people dancing in the streets with a medley of "Best of My Love" and "I'm Every Woman." Then, she kept the party going with a performance of her hit single "Spotlight."

Watch Jennifer perform "Spotlight."

After performing for the first time since giving birth to her son, David, Jennifer told Oprah about being a new mom. "It is the best feeling in the world. No words describe it," she said. "It's something you have to experience. It's like no other."

Go backstage with Jennifer.

Microphones were passed through the crowd as music legend James Taylor performed a sing-along rendition of his hit "How Sweet It Is."

James Taylor and Owen Young perform You've Got a Friend."

Alongside Owen Young, a cellist from the Boston Symphony Orchestra, James performed another classic, "You've Got a Friend."

Watch James sing "You've Got a Friend."

After James finished his set, Oprah urged the audience to go out and buy his latest album, Covers.

Country supergroup Rascal Flatts—Gary LeVox, Jay DeMarcus and Joe Don Rooney—were at home in Nashville when they got the invitation to Oprah's kickoff party...16 hours before the show! After a short flight, they took Oprah's stage to perform their hit single "Summer Nights."

Rascal Flatts performs Life Is a Highway.

Rascal Flatts kept the party going with a special performance of "Life Is a Highway," a song they recorded for the animated film Cars.

Watch Gary, Jay and Joe Don sing "Life Is a Highway."

Night falls over Oprah's Season 24 Kickoff Party.

The calendar may say it's almost fall, but that didn't stop this Chicago crowd from rocking out to "Summer Nights" with Gary, Joe Don and Jay.

Go backstage with Rascal Flatts.

Fans cheer at Oprah's Season 24 Kickoff Party.

As the sun set over Chicago, devoted fans celebrated the new season with Oprah and her special guests.

24 Memorable Moments