Oprah Winfrey, an American talk show host, television producer, actress, author, and media proprietor, rose to fame through her nationally syndicated talk show, *The Oprah Winfrey Show*, which aired for 25 years. Known as the "Queen of All Media," she became the wealthiest African-American of the 20th century and the world's only Black billionaire at one point. Winfrey is often recognized as one of the most influential women globally.
In 1933, Vernon Winfrey, Oprah Winfrey's father, was born. He was a coal miner turned barber turned city councilman.
In 1935, Vernita Lee, Oprah Winfrey's mother, was born. She later worked as a housemaid.
In 1937, Zora Neale Hurston's novel "Their Eyes Were Watching God" was published. This book would later be adapted into a made-for-television film by Harpo Productions in 2005, starring Halle Berry.
On January 29, 1954, Oprah Gail Winfrey was born as Orpah Gail Winfrey in Kosciusko, Mississippi, to a teenaged mother, Vernita Lee, and father Vernon Winfrey. Her first name was misspelled on her birth certificate but she became known as Oprah.
In 1962, due to her mother's difficulty in raising both daughters, Oprah Winfrey was temporarily sent to live with her father in Nashville, Tennessee.
In 1971, Oprah Winfrey met William "Bubba" Taylor at Tennessee State University shortly after breaking up with Otey. According to CBS journalist George Mair, Taylor was Winfrey's "first intense, to-die-for love affair".
In June 1976, William "Bubba" Taylor was unwilling to leave Nashville with Winfrey when she moved to Baltimore to work at WJZ-TV, which led to their breakup.
In 1976, Oprah Winfrey moved to Baltimore's WJZ-TV to co-anchor the six o'clock news, making her the first black female news anchor at Nashville's WLAC-TV.
In 1977, Oprah Winfrey was removed as co-anchor at WJZ-TV and transitioned to lower profile positions within the station.
On August 14, 1978, Oprah Winfrey joined Richard Sher as co-host of WJZ's local talk show People Are Talking.
On September 8, 1981, Oprah Winfrey wrote a suicide note to her best friend Gayle King because she was feeling depressed from an unrequited love affair with a married man.
On January 2, 1984, the first episode of AM Chicago aired with Oprah Winfrey as the host. She was hired by the station's general manager, Dennis Swanson.
In 1985, Haitian filmmaker Reginald Chevalier claimed that he appeared as a guest on Oprah Winfrey's Chicago talk show and began a relationship with her, which ended when she met Stedman Graham.
In 1985, Oprah Winfrey co-starred in Steven Spielberg's "The Color Purple" as Sofia. She was nominated for an Academy Award for Best Supporting Actress for her performance.
In 1985, Oprah Winfrey purchased her first condominium in Chicago's Water Tower Place.
In 1985, Oprah Winfrey was allegedly involved in a drug-related love affair. Self-proclaimed former boyfriend Randolph Cook said they lived together for several months and did drugs.
On September 8, 1986, the first episode of The Oprah Winfrey Show was broadcast nationwide. This marked a significant expansion for the show.
In 1986, Oprah Winfrey acknowledged that her father taking her in significantly changed her life for the better, providing structure and expectations.
In 1986, Oprah Winfrey began her relationship with Stedman Graham, who has been her partner since then.
In 1986, Oprah Winfrey publicly announced on her TV show that she had been molested by her cousin, uncle, and a family friend, starting when she was nine years old.
In 1986, The Oprah Winfrey Show, originating from Chicago, began its national syndication run, which would last for 25 years. This marked a significant milestone in Oprah Winfrey's career.
In 1987, Oprah Winfrey finally delivered her final paper and earned her degree from Tennessee State University, a historically black institution, after having been a successful television personality for some time.
In August 1988, Time magazine reported the much-publicized contest of the audience share between the shows of Oprah Winfrey and Phil Donahue, which was the subject of enormous scrutiny.
The November 1988 issue of Ms. observed that Oprah Winfrey made fat sexy and elegant in a society where fat is taboo.
In 1988, Oprah Winfrey purchased a 164-acre property in Rolling Prairie, Indiana, as her weekend refuge.
In 1989, Jeffrey, Oprah Winfrey's half-brother, died of AIDS-related causes.
In 1989, Oprah Winfrey produced and co-starred in the drama miniseries The Women of Brewster Place and its short-lived spin-off, Brewster Place.
In 1989, Oprah Winfrey was accepted into the NAACP Image Award Hall of Fame.
In 1990, Oprah Winfrey felt betrayed when a family member sold the story of her premature son's death to the National Enquirer.
In November 1992, Oprah Winfrey and Stedman Graham were engaged to be married, but the ceremony never took place.
From 1992 to 1994, Oprah Winfrey moderated three ABC Afterschool Specials, contributing to educational programming for young audiences.
In 1992, Oprah Winfrey purchased condos adjoining her Water Tower Place condo and an 80-acre compound in Telluride, Colorado.
In 1993, Oprah Winfrey hosted "Michael Jackson Talks ... to Oprah" with Michael Jackson. The interview became the fourth most-watched event in American television history and the most-watched interview ever, with 36.5 million viewers.
From 1992 to 1994, Oprah Winfrey moderated three ABC Afterschool Specials, contributing to educational programming for young audiences.
In 1994, Oprah Winfrey was inducted into the National Women's Hall of Fame, recognizing her achievements and contributions.
Since 1994, Oprah Winfrey abandoned traditional talk-show fare for more edifying content, marking a significant shift in the focus of her program.
On April 16, 1996, during a show about mad cow disease with Howard Lyman, Oprah Winfrey stated that she was stopped cold from eating another burger.
Between 1996 and 2000, Oprah Winfrey purchased a total of five condos in different development areas of Fisher Island, Florida.
Late in 1996, Oprah Winfrey introduced the Oprah's Book Club segment to her television show, which had a significant impact on book sales and popular attention to literature.
In April 1997, Oprah Winfrey played the therapist in "The Puppy Episode" on the sitcom Ellen, where the character (and the real-life Ellen DeGeneres) came out as a lesbian.
In 1997, Oprah Winfrey played the therapist on an episode of the sitcom "Ellen" in which Ellen DeGeneres came out of the closet, sparking rumors about Winfrey and King being gay.
In 1997, Randolph Cook tried to sue Oprah Winfrey for $20 million for allegedly blocking a tell-all book about their alleged relationship.
In October 1998, Oprah Winfrey produced and starred in the film "Beloved", based on Toni Morrison's Pulitzer Prize-winning novel of the same name. She prepared for her role by experiencing a 24-hour simulation of slavery.
In 1998, Oprah Winfrey became the first woman and first African American to top Entertainment Weekly's list of the 101 most powerful people in the entertainment industry.
In 1998, Oprah Winfrey began 'Change Your Life TV', marking a turn to spirituality and self-help on her show, cementing her role as a spiritual leader.
In 1998, Oprah Winfrey began an ongoing conversation with Gary Zukav, an American spiritual teacher, who appeared on her television show 35 times, and she keeps a copy of Zukav's "The Seat of the Soul" by her bedside.
In 1998, Oprah Winfrey created Oprah's Angel Network, a charity that supported charitable projects and provided grants to nonprofit organizations around the world.
In 1998, Oprah Winfrey hosted a week-long Caribbean cruise for Maya Angelou and 150 guests for Angelou's 70th birthday.
In early 1998, Texas cattlemen sued Oprah Winfrey and Howard Lyman for "false defamation of perishable food" and "business disparagement," claiming that Winfrey's remarks on April 16, 1996 sent cattle prices tumbling.
By the year 2000, with a net worth of $800 million, Oprah Winfrey is believed to have been the richest African American of the 20th century.
In 2000, Oprah Winfrey purchased an estate for Gayle King in Greenwich, Connecticut, and acquired five condos in Fisher Island, Florida.
In 2000, Oprah Winfrey was awarded the Spingarn Medal from the NAACP for her contributions.
In 2001, Lavern Chatman, for whom Oprah Winfrey held a fundraiser in April 2014, was found liable for her role in a scheme to defraud District of Columbia nursing-home employees.
In 2001, Oprah Winfrey sold all five of her Fisher Island condos and purchased a 42-acre estate in Montecito, California, which she has called "The Promised Land".
Twelve days after the September 11 attacks, in 2001, New York mayor Rudy Giuliani asked Oprah Winfrey to serve as host of a Prayer for America service at New York City's Yankee Stadium.
From 2002 to 2006, Oprah Winfrey's Oprah After the Show program aired on Oxygen, the women's cable television network she co-founded.
In 2002, "Fortune" called "O, the Oprah Magazine" the most successful start-up ever in the industry.
In 2002, Christianity Today published an article called "The Church of O," concluding that Oprah Winfrey had emerged as an influential spiritual leader.
In 2002, George W. Bush invited Oprah Winfrey to join a US delegation planning to go to Afghanistan to celebrate the return of Afghan girls to school, however, Winfrey refused to participate, and the trip was postponed.
In 2002, Oprah Winfrey was the recipient of the first Bob Hope Humanitarian Award at the Emmy Awards for services to television and film.
In February 2003, Patricia, Oprah Winfrey's younger half-sister, died of causes related to cocaine addiction at age 43.
In February 2003, a series on Oprah Winfrey's show, featuring clips from people worldwide asking America not to go to war, was interrupted in several East Coast markets by network broadcasts of a press conference by President George W. Bush and Colin Powell.
In November 2003, a Gallup poll estimated that 73% of American adults had a favorable view of Oprah Winfrey.
In 2003, Oprah Winfrey became the first black woman billionaire in the world.
In 2003, Oprah Winfrey listed her compound in Rolling Prairie, Indiana.
From 2004 to 2006, Oprah Winfrey was listed as the world's only black billionaire on Forbes' list of The World's Billionaires.
From 2004 to 2011, Oprah Winfrey was named one of the most influential people by TIME.
In 2004, Oprah Winfrey and her team filmed an episode of her show, "Oprah's Christmas Kindness", in which Winfrey travelled to South Africa to bring attention to the plight of young children affected by poverty and AIDS, distributing Christmas presents to 50,000 children.
In 2004, Oprah Winfrey became the first Black person to rank among the 50 most generous Americans.
In 2004, Oprah Winfrey published a magazine called "O At Home".
In 2004, Oprah Winfrey sold her compound in Rolling Prairie, Indiana.
On December 1, 2005, Oprah Winfrey made her first appearance on the Late Show with David Letterman in 16 years to promote "The Color Purple" musical. The episode was considered a major television event, attracting a large audience for Letterman.
From 2005 to 2008, the circulation of "O, the Oprah Magazine" declined by more than 10 percent to 2.4 million.
In 2005, "The Color Purple" opened as a Broadway musical, with Oprah Winfrey credited as a producer. Also in 2005, Harpo Productions released a film adaptation of Zora Neale Hurston's 1937 novel "Their Eyes Were Watching God", starring Halle Berry.
In 2005, Forbes named Oprah Winfrey the world's most powerful celebrity.
In 2005, Kathleen Rooney described Winfrey as "a serious American intellectual who pioneered the use of electronic media, specifically television and the Internet, to take reading – a decidedly non-technological and highly individual act – and highlight its social elements and uses in such a way to motivate millions of erstwhile non-readers to pick up books" in the book Reading with Oprah: The Book Club that Changed America.
In 2005, Oprah Winfrey announced a weight-loss book co-authored with Bob Greene, reportedly breaking the record for the world's highest book advance fee.
In 2005, Oprah Winfrey was named the greatest woman in American history as part of a public poll as part of The Greatest American.
On February 9, 2006, Oprah Winfrey signed a three-year, $55-million contract with XM Satellite Radio to establish a new radio channel.
In the August 2006 issue of "O, the Oprah Magazine", Oprah Winfrey addressed persistent rumors about her and Gayle King being gay, explaining the deep bond between them and denying any sexual relationship.
Oprah & Friends began broadcasting on September 25, 2006, from a new studio at Winfrey's Chicago headquarters on XM Radio Channel 156.
From 2004 to 2006, Oprah Winfrey was listed as the world's only black billionaire on Forbes' list of The World's Billionaires.
In 2006, Maureen Dowd stated that Oprah Winfrey is the top alpha female in the country and has more credibility than the president.
In 2006, Oprah Winfrey confronted James Frey on her show after his book, "A Million Little Pieces", was found to contain fabrications.
In 2006, Oprah Winfrey purchased a co-op apartment along Lake Shore Drive in downtown Chicago, with plans to move there permanently. However, the property remained unused.
In 2006, Oprah Winfrey recalled past controversies, including hate mail received after a show titled "Is War the Only Answer?", where she was accused of being un-American for even raising the question.
In 2006, Oprah Winfrey sold her stake in Oxygen and moved her Oprah After the Show program to Oprah.com.
In 2006, Oprah Winfrey voiced Gussie the goose in the movie "Charlotte's Web".
In 2006, Oprah Winfrey was the highest-paid television entertainer in the United States, earning an estimated $260 million during the year.
In 2006, a genetic test determined that Oprah Winfrey's matrilineal line originated among the Kpelle ethnic group from Liberia. Her genetic makeup was determined to be 89% Sub-Saharan African, 8% Native American, and 3% East Asian.
In 2006, rappers Ludacris, 50 Cent, and Ice Cube criticized Oprah Winfrey for what they perceived as an anti-hip hop bias.
In the summer of 2006, Oprah Winfrey took her staff and their families, totaling 1,065 people, on vacation to Hawaii to celebrate two decades on national TV and to thank them for their hard work.
The January 2009 issue of "O, the Oprah Magazine" was the best-selling issue since 2006.
In January 2007, another Gallup poll estimated that 74% of American adults had a favorable view of Oprah Winfrey.
In January 2007, the Oprah Winfrey Leadership Academy for Girls opened in Henley on Klip south of Johannesburg, South Africa, with an enrollment of 150 pupils.
On September 8, 2007, Oprah Winfrey held a fundraiser for Barack Obama at her Santa Barbara estate to support his presidential campaign.
On September 10, 2007, David Letterman made his first appearance on The Oprah Winfrey Show, which was filmed in New York City for its season premiere.
In October 2007, a Gallup poll estimated that 66% of American adults had a favorable view of Oprah Winfrey.
On December 9, 2007, Oprah Winfrey joined Barack Obama for a rally in Columbia, South Carolina, which drew a crowd of nearly 30,000 people, the largest for any political event of 2007.
In December 2007, Oprah Winfrey joined Barack Obama for a series of rallies in the early primary states of Iowa, New Hampshire, and South Carolina to support his presidential campaign.
In December 2007, a Fox News poll put the figure at 55% of American adults had a favorable view of Oprah Winfrey.
By 2007, Oprah Winfrey was often ranked as the most influential woman in the world, recognizing her significant impact and influence across various fields.
In 2007, Oprah Winfrey began to endorse the self-help program "The Secret". The Secret claims that people can change their lives through positive thoughts or 'vibrations'.
In 2007, Oprah Winfrey voiced Judge Bumbleton in "Bee Movie", co-starring Jerry Seinfeld and Renée Zellweger.
In 2007, The Wall Street Journal reported that MBC 4, an Arab satellite channel, centered its entire programming around reruns of Oprah Winfrey's show because it was drawing record numbers of female viewers in Saudi Arabia.
In 2007, USA Today ranked Oprah Winfrey as the most influential woman and most influential black person of the previous quarter-century.
On January 15, 2008, Oprah Winfrey and Discovery Communications announced plans to change Discovery Health Channel into a new channel called OWN: Oprah Winfrey Network.
In September 2008, Oprah Winfrey faced criticism after the Drudge Report claimed she refused to have Sarah Palin on her show due to her support for Barack Obama. Winfrey denied the report.
By 2008, Oprah Winfrey's yearly income had increased to $275 million, further solidifying her status as a top entertainer.
By 2008, the ratings for The Oprah Winfrey Show declined to around 7.3 million viewers, though it remained the highest-rated talk show.
In 2008, Forbes named Oprah Winfrey the world's most powerful celebrity.
In 2008, Oprah Winfrey endorsed Barack Obama for president, and economists estimate that this endorsement was worth over a million votes in the Democratic primary race.
In 2008, Oprah Winfrey endorsed Barack Obama in the presidential race, estimated to have been worth about one million votes. Also in 2008, she formed her own network, the Oprah Winfrey Network (OWN).
In 2008, Oprah Winfrey endorsed author and spiritual teacher Eckhart Tolle and his book, "A New Earth: Awakening to Your Life's Purpose", which sold several million extra copies after being selected for her book club.
In 2008, Oprah Winfrey sold her penthouse apartment in Atlanta. That year, she also listed Gayle King's estate and purchased her (through her second LLC Sophie's Penthouse) a penthouse apartment in midtown Manhattan, New York City.
In 2008, Oprah Winfrey threw "an extravagant 80th birthday celebration" for Maya Angelou at Donald Trump's Mar-a-Lago club in Palm Beach, Florida.
In 2008, Oprah Winfrey was named as the Person of the Year by animal-rights group People for the Ethical Treatment of Animals (PETA) for using her fame and listening audience to help animals.
In 2008, Oprah Winfrey's magazine "O At Home" ceased publication.
In 2008, Oprah Winfrey's show was airing in 140 countries internationally and seen by an estimated 46 million people in the US weekly.
In 2008, The New York Times reported that The Oprah Winfrey Show, with Arabic subtitles, was broadcast twice each weekday on MBC 4.
In 2008, as chairman of Harpo Inc., Oprah Winfrey was named the most powerful woman in entertainment by The Hollywood Reporter.
In late 2008, Oprah Winfrey's company Harpo Films signed an exclusive output pact to develop and produce scripted series, documentaries, and movies exclusively for HBO.
In January 2009, the issue of "O, the Oprah Magazine" was the best-selling issue since 2006.
On November 18, 2009, Sarah Palin appeared on Oprah Winfrey's show after the election, which Winfrey said she would do.
According to the Harris poll, in 2009 Oprah Winfrey was named America's favorite television personality.
In 2009, OWN: Oprah Winfrey Network was initially scheduled to launch but was delayed.
In 2009, Oprah Winfrey apologized to James Frey for the public confrontation regarding his book, "A Million Little Pieces", that was aired in 2006.
In 2009, Oprah Winfrey filmed a series of interviews in Denmark, highlighting its citizens as the happiest people in the world.
In 2009, Oprah Winfrey provided the voice for Eudora, Princess Tiana's mother, in Disney's "The Princess and the Frog."
In 2009, Oprah Winfrey was criticized for allowing actress Suzanne Somers to appear on her show to discuss hormone treatments not accepted by mainstream medicine. She also faced criticism for not being tough enough on celebrity guests.
In May 2010, with Oprah's show ending, Oprah's Angel Network stopped accepting donations and was shut down.
In September 2010, Oprah Winfrey was voted 38th in the list of "The World's 50 Most Influential Figures 2010" by the British magazine New Statesman.
In 2010, Bill O'Reilly of Fox News criticized Oprah Winfrey's shows filmed in Denmark for promoting a left-wing society.
In 2010, Forbes named Oprah Winfrey the world's most powerful celebrity.
In 2010, Life magazine named Oprah Winfrey one of the 100 people who changed the world.
In 2010, Oprah Winfrey learned that she had a second half-sister named Patricia, who had been put up for adoption.
In 2010, Oprah Winfrey narrated the US version of the BBC nature program "Life" for Discovery.
In 2010, Oprah Winfrey remained among the top 50 most generous Americans, a position she had held since 2004.
After being delayed from its original scheduled launch in 2009, OWN: Oprah Winfrey Network officially launched on January 1, 2011.
On May 25, 2011, the series finale of The Oprah Winfrey Show aired, marking the end of its long and influential run.
From 2004 to 2011, Oprah Winfrey was named one of the most influential people by TIME.
In 2011, Oprah Winfrey gifted a home in Douglasville, Georgia, which she had purchased in 2005, to a family member.
In 2011, The Oprah Winfrey Show concluded its 25-year run in national syndication. This marked the end of an era for the influential talk show.
As of 2012, Oprah Winfrey had given over 400 scholarships to Morehouse College in Atlanta, Georgia.
By 2012, Oprah Winfrey had given away approximately $400 million to educational causes.
In 2012, Oprah Winfrey sold her unused co-op apartment along Lake Shore Drive in downtown Chicago.
In 2013, Forbes named Oprah Winfrey the world's most powerful celebrity.
In 2013, Oprah Winfrey donated $12 million to the Smithsonian's National Museum of African American History and Culture. Later that year, President Barack Obama awarded her the Presidential Medal of Freedom.
In 2013, Oprah Winfrey starred in the film "The Butler" directed by Lee Daniels. Her performance garnered Oscar buzz, though she was not nominated.
In 2013, Oprah Winfrey was awarded the Presidential Medal of Freedom by President Barack Obama, recognizing her contributions to society and culture.
In April 2014, Oprah Winfrey spoke for over 20 minutes at a fundraiser in Arlington, Virginia, for Lavern Chatman, a Democratic Party candidate for election to the U.S. House of Representatives.
As of 2014, Oprah Winfrey had a net worth in excess of 2.9 billion dollars and had overtaken former eBay CEO Meg Whitman as the richest self-made woman in America.
In 2014, Oprah Winfrey ranked 14th on Forbes' list of the world's 100 most powerful women.
In 2015, Oprah Winfrey purchased another property in Telluride, and later that year, expanded her Montecito compound with another 23-acre estate and yet another 44-acre dedicated crop and equestrian preserve. That year she also sold both of her downtown Chicago homes.
In 2015, Oprah Winfrey's memoir, "The Life You Want", was announced, following her tour of the same name.
Following the launch of the Super Soul Sunday and SuperSoul Sessions programs on Harpo Productions' SuperSoul TV, in 2016 Oprah Winfrey selected 100 people for the SuperSoul 100 list of "innovators and visionaries who are aligned on a mission to move humanity forward".
In 2016, Oprah Winfrey endorsed Hillary Clinton in the presidential election and referred to Republican candidate Donald Trump as a "demagogue".
In 2016, the publication of Oprah Winfrey's memoir, "The Life You Want", was "indefinitely postponed".
In January 2017, CBS announced that Oprah Winfrey would join 60 Minutes as a special contributor on the Sunday evening news magazine program.
In September 2017, Oprah Winfrey started as a special contributor on 60 Minutes.
In 2017, the planned publication of Oprah Winfrey's memoir, "The Life You Want", was scheduled.
In a 2017 interview with Vanity Fair, Oprah Winfrey explained that she didn't want babies after the loss of her infant child at age 14 because she didn't believe she would have been a good mom for babies.
In 2018, Oprah Winfrey canvassed door-to-door for Georgia gubernatorial Democratic nominee Stacey Abrams and donated $500,000 to the March for Our Lives student demonstration in favor of gun control in the United States.
In 2018, Oprah Winfrey denied any plans to run for president, stating that while she was honored by the suggestion, she believed it was "not a clean business" and "would kill me".
In 2018, Oprah Winfrey left 60 Minutes. The National Museum of African American History and Culture opened a special exhibit on Winfrey's cultural influence through television.
In 2018, Oprah Winfrey obtained two adjoining parcels of land totaling 23 acres including the Madroneagle compound on Orcas Island, Washington and sold her last home property in the Chicago area from Elmwood Park.
In 2018, Oprah Winfrey starred as Mrs. Which in the film adaptation of "A Wrinkle in Time". She also lent her voice to the animated virtual-reality short film "Crow: The Legend".
In 2018, Vernita Lee, Oprah Winfrey's mother, passed away.
In early 2018, Oprah Winfrey met with Mohammad bin Salman, the crown prince and de facto ruler of Saudi Arabia, when he visited the United States.
In late 2019, Oprah Winfrey expanded her Montecito home-base compound to 70 contiguous acres with the purchase of a four-acre complex from actor Jeff Bridges.
On March 21, 2020, Oprah Talks COVID-19 debuted on Apple TV+ during the COVID-19 pandemic.
In July 2020, it was announced that "O Magazine" would end its regular print publications after the December 2020 issue.
On July 30, 2020, The Oprah Conversation debuted with Winfrey "[continuing] to explore impactful and relevant topics with fascinating thought leaders from all over the world".
In the December 2020 issue, Oprah Winfrey thanked readers and acknowledged it was the magazine's "final monthly print edition".
In 2020, there were calls for Oprah Winfrey to denounce Dr. Oz due to his comments about coronavirus and promotion of a poorly vetted drug as a cure.
Leading up to the 2020 election, there was media speculation that Oprah Winfrey might run for president, but she ultimately denied any plans to do so and later campaigned for Joe Biden during the general election.
In 2021, Oprah Winfrey conducted an interview with Meghan, Duchess of Sussex, and her husband Prince Harry, which was broadcast globally and received international media attention.
In 2021, Oprah Winfrey sold her Orcas Island compound and purchased another compound in Montecito further away from her home-base compound.
In 2021, Oprah Winfrey was elected as a member of the American Academy of Arts and Sciences, acknowledging her contributions to arts, sciences, and public life.
As of 2022, Oprah Winfrey continues to reside at her Montecito estate, which she refers to as "The Promised Land".
As of 2022, Oprah's real-estate portfolio is estimated to total approximately $127 million.
In 2022, Oprah Winfrey endorsed Democrat John Fetterman in the Pennsylvania Senate election and Baltimore author Wes Moore in the Maryland gubernatorial election.
In 2022, Oprah Winfrey flipped her Montecito property, splitting it into two properties, one of which was sold to her property manager and longtime personal trainer Bob Greene, and the other to actress Jennifer Aniston.
In 2022, Oprah Winfrey set up OWN Your Vote, a nonpartisan group dedicated to voter registration and a get-out-the-vote campaign focused on providing Black women with tools and resources to vote in the November election.
In 2022, Vernon Winfrey, Oprah Winfrey's father, passed away.
On January 18, 2023, Oprah Winfrey attended and spoke at Wes Moore's gubernatorial inauguration in Maryland after endorsing him in the 2022 primary.
In 2023, Oprah Winfrey purchased 870 acres of land in Maui for $6.6 million.
In 2023, Oprah Winfrey ranked 31st on Forbes' list of the world's 100 most powerful women.
On August 21, 2024, Oprah Winfrey endorsed Kamala Harris in the 2024 United States presidential election at the 2024 Democratic National Convention.
In 2024, ABC aired "AI and the Future of Us: An Oprah Winfrey Special", a television special hosted by Oprah Winfrey. The show explored the impact of artificial intelligence (AI) on daily life and featured interviews with tech industry figures like OpenAI CEO Sam Altman and Bill Gates.
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