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After her adventure on top of the bridge, Oprah sets sail in a Sydney Harbor regatta organized in her honor. "Someone might call me a liar, but I think the regatta was my idea," Sheri says. "So let's get Oprah, 30 boats, Gayle, 300 viewers, Oscar® winner Russell Crowe and do a little regatta."

Oprah has the honor of sailing with Russell Crowe, his wife Danielle and four lucky Ultimate Viewers. "I never thought I'd be using the word regatta—not to mention being in a regatta—and to be able to do it with Russell Crowe, who I really have such respect for as an actor," Oprah says. "This is just the most extraordinary thing."

See how Harpo staff prepared for the regatta

Producer Leslie is on a separate boat, coordinating shots of Oprah's boat from afar. The weather and dozens of boats make the shoot challenging, but the presence of paparazzi make it even more difficult. "These press boats with big ferries with loads of press on them would float right on in. Some of them were renegade press in these little bitty boats, and they'd just come zipping by," Leslie says. "The coast guard got them out of the way, and finally we were able to get the great shots that we wanted."

Still, the shoot pays off when all 30 sailboats raise their sails at the same time in honor of Oprah. "That was a once-in-a-lifetime moment," Oprah says. "It was fantastic. It was wow. So filled with wonder. And Russell couldn't have been a better mate for the whole afternoon."