Oprah also thought Leonardo DiCaprio was Justin Timberlake.
During The Oprah Winfrey Show, Oprah greeted many guests through her doors. In the show's 25-season history, Oprah held herself with composure as she spoke with the biggest names in the world. Would you believe she doesn't hang out with celebrities? During her time on The Ellen Show, she mentioned she doesn't even recognize celebrities when they're looking low-key. "When I did my show, famous people came on and looked like themselves" Winfrey pointed out, "at your party, they're all disguised." Ellen was celebrating her 60th birthday, and she invited what Oprah described as a great mix of friends.
Oprah goes on to recall the different people she couldn't recognize. A young man in a baseball cap turned out to be RnB star, The Weeknd. She tricked a man who she initially mistook for Justin Timberlake into revealing himself as Leonardo DiCaprio. After The Weeknd told the elite actor he enjoyed his latest film, Leo mentioned it wasn't his favorite to shoot. Oprah then slyly asked, "what was your favorite film?" to which he responded, "The Aviator." The Harpo Productions owner stuck around after her Ellen Show segment to surprise actor-comedian, Tiffany Haddish, who was brought to tears.