49. Though the Academy has done a world of good for its students, it's also faced its share of criticism and controversy. Most notably, in its first year of operation, a female staffer was accused of physically and sexually assaulting students. Oprah flew to the school to meet with officials and parents and the matron was eventually arrested after seven students submitted statements detailing their alleged assaults.
50. After Oprah donated $12 million to the Smithsonian's National Museum of African American History and Culture, President Barack Obama awarded her with the Presidential Medal of Freedom, the highest civilian award in the United States that recognizes people who have made "an especially meritorious contribution to the security or national interests of the United States, world peace, cultural or other significant public or private endeavors."
51. When Oprah graced the cover of Vogue in 1998, she was the first African-American TV and film celebrity to do so. And famed editrix Anna Wintour told her to lose weight to do it.
"It was a very gentle suggestion," Anna later recalled on 60 Minutes. "I went to Chicago to visit Oprah, and I suggested that it might be an idea that she lose a little bit of weight. I said simply that you might feel more comfortable. She was a trooper!"
52. Oprah's main residence is a 23,000 square-foot Georgian estate in Montecito that she's nicknamed "The Promised Land." Purchased for somewhere around $50 million, the original property was 42 acres, but when her neighbor died in 2016, she bought up the additional 23 acres of land.
53. The additional Montecito property was purchased for $28.8 million. The "once in a lifetime property" hadn't been on the market in over 30 years. The house has horse pens, covered stalls and riding areas, but Oprah didn't want the horses, so they weren't also included in the sale.
54. She also owns 163 acres of property in the Hana area of Maui and a five-bedroom home in Telluride, Colo.
55. According to Politico, Oprah's Montecito water bill was "just shy of $125,000" in 2013. The following year, during the California drought, she had tanker trucks filled with water shipped in to keep her grounds lush and green.
56. More than a decade ago, Oprah purchased a Global Express XRS executive jet from Bombardier Aerospace for a whopping $42 million.
57. In 2006, she anonymously purchased Gustav Klimt's "Adele Block-Bauer II" for $87.9 million. And 10 years later, she decided she didn't want it anymore, with TIME reporting that she sold it to a Chinese collector for around $150 million.
58. Her greatest extravagance? "Flying in English muffins from Napa Valley," she told People's Jess Cagle in 2017. "There's a specific English muffin made by these two women at this wonderful bakery in Napa Valley. I know it's not a good carbon footprint to fly in your English muffins but…" The muffins come from The Model Bakery and cost $40 for a dozen and a jar of Clif Family preserves to spread on them.
59. And yet when asked about her favorite gift to receive, she told E! News at the 2024 Golden Globes, "The best thing that anybody can ever do for me is a personal handwritten note. That means more to me than anything."
In fact, she added, "I have a box now of all the notes from the heart."
60. According to Forbes' 2018 list of America's richest self-made women, Oprah ranked No. 6. She remains the richest African-American woman on the list.
61. In 2017, Oprah admitted to Ellen that she went to the bank for the first time since 1998 to deposit a $2 million check. "I just wanted to," she said. "I just wanted to do it. I stood in line — just to do it!" As for how it felt? "Fantastic," she revealed.
62. The first time Oprah ever publicly endorsed a candidate running for office was in 2008 when she threw her weight behind eventual winner Obama. She held a 2007 fundraiser for him at her Montecito estate and then joined him at a series of rallies in early primary states of Iowa, New Hampshire and South Carolina.
63. In 2018, she canvassed door-to-door for Georgia gubernatorial Democratic candidate Stacey Abrams.
64. A course focusing on Oprah's business acumen has been taught at the University of Illinois, entitled "History 298: Oprah Winfrey, the Tycoon"
65. In 2006, Oprah's deal for a book about keeping weight under control was announced to top Bill Clinton's $12 million record advance for his autobiography, though the exact number wasn't revealed.
66. After testifying before the U.S. Senate Judiciary Committee to establish a national database of convicted child abusers, she initiated the National Child Protection Act which was signed into law in 1993.
67. In 2005, Oprah launched Oprah's Child Predator Watch List and her pledge to provide a $100,000 reward per case to those individuals whom the FBI or local law enforcement officials say provided critical information leading to the capture and arrest of fugitives featured on her show or website.
68. After the loss of her son as a teenager, Oprah's famously never had any other children, openly admitting over the years that she's never had the desire or felt bad about it.
"If I had kids, my kids would hate me," she told The Hollywood Reporter in 2013. "They would have ended up on the equivalent of the Oprah show talking about me; because something [in my life] would have had to suffer and it would've probably been them."
But in 2019, while speaking to People, she admitted that the girls at her school who call her Mom O are "the daughters I did not have."
69. Since June 2018, she's been working exclusively with Apple on a multi-year content partnership, under which she creates new original programs for new streaming service Apple TV+. And on Nov. 1, 2019, she revived her famous Book Club for a new series featuring an Oprah interviewing the authors of her chosen books.
70. Another passion project: Serving as a producer on the 2023 big-screen adaption of The Color Purple Broadway musical. "I finally got my name on the poster," she raved to E! News at the Golden Globes, where the film was up for two awards. "My name was not on the poster for the original film because I wasn't a big enough name to have my name on the poster."