Gayle flew out to Chicago—with 9-month-old daughter Kirby in tow—and had a front-row seat at an Oprah Show taping. In between the show taping and playing with Kirby, Gayle interviewed Oprah about her newfound fame and where she saw her career heading.
Watch footage from Gayle's 1987 trip to Chicago
Even then, people were curious about Oprah's plans for the future—and Gayle was no exception. When Gayle asked her best friend how much longer The Oprah Show would be on the air, Oprah told her just four more years! "I love doing the show, but I'm tired. I'm not tired of doing the show, but if I could just have a day off, I'd be thrilled. So I'm going to do it for as long as it still feels good to me, which will be for a while," Oprah said at the time.