Oprah Pulls the Wagon of Fat (1988)

The show that Oprah considers her "biggest, fattest" mistake is also the highest-ranking “Oprah” episode ever! To represent her recent 67-pound weight loss, Oprah wheeled a wagon of fat onto the stage. "I had literally starved myself for four months—not a morsel of food—to get into that pair of size 10 Calvin Klein jeans," Oprah remembers. "Two hours after that show, I started eating to celebrate—of course, within two days those jeans no longer fit!"