Oprah Winfrey

American media mogul Oprah Winfrey is well known for her talk show broadcasted in Chicago, The Oprah Winfrey Show, the highest-rated TV program in history, which ran from 1986 to 2011. Given credit for being the “Queen of All Media,” Winfrey never had children or ever got married, though she was once engaged to Stedman Graham, whom she met in a charity event in 1986.

When People magazine interviewed the media mogul, Winfrey said she gave marriage and kids some thinking, but in the end, she decided against both and never regretted her decision. Even though she doesn’t have any kids or never get married, that didn’t stop her from making investments in her real estate portfolio. For 30 years, Winfrey’s primary residence was her mansion in Chicago, which featured 9,625 square feet of living space. However, she eventually sold it back in 2015 for $4.625 million.