Oprah Winfrey is an influential American talk show host, television producer, actress, author, and media proprietor, widely recognized for The Oprah Winfrey Show, which aired for 25 years. Known as the "Queen of All Media," she was the wealthiest African-American of the 20th century and, at one point, the world's only black billionaire. She is consistently ranked among the most influential women globally.
On April 15, 1900, Hattie Mae (Presley) Lee, Oprah Winfrey's maternal grandmother, was born. She passed away on February 27, 1963.
In 1933, Vernon Winfrey, Oprah Winfrey's father, was born. He passed away in 2022.
In 1935, Vernita Lee, Oprah Winfrey's mother, was born. She passed away in 2018.
On January 29, 1954, Oprah Gail Winfrey, originally named Orpah Gail Winfrey, was born in Kosciusko, Mississippi. She is now known as an American talk show host, television producer, actress, author, and media proprietor.
In 1962, Oprah Winfrey was temporarily sent to live with her father in Nashville, Tennessee, due to her mother's difficulty raising both daughters.
On February 27, 1963, Hattie Mae (Presley) Lee, Oprah Winfrey's maternal grandmother, passed away.
In 1971, Oprah Winfrey met William "Bubba" Taylor at Tennessee State University, initiating what CBS journalist George Mair described as her "first intense, to-die-for love affair." This relationship marked a significant personal connection for Winfrey during that year.
In June 1976, Winfrey moved to Baltimore to work at WJZ-TV. The move ended her relationship with William "Bubba" Taylor, who was unwilling to relocate from Nashville with her, marking a pivotal moment in her career and personal life.
In 1976, Oprah Winfrey moved to Baltimore's WJZ-TV to co-anchor the six o'clock news.
In 1977, Oprah Winfrey was removed as co-anchor and worked in lower profile positions at the station.
On August 14, 1978, Oprah Winfrey co-hosted WJZ's local talk show People Are Talking.
On September 8, 1981, Winfrey wrote a suicide note to her best friend, Gayle King, during a period of depression. She later reflected on the note, stating she realized she couldn't go through with it as she'd miss out on something good.
On January 2, 1984, Oprah Winfrey began hosting WLS-TV's AM Chicago.
In 1985, Oprah Winfrey co-starred in Steven Spielberg's "The Color Purple" as Sofia, a distraught housewife. She was nominated for an Academy Award for Best Supporting Actress for her performance.
In 1985, Oprah Winfrey first purchased a condominium in Chicago's Water Tower Place.
In 1985, Oprah Winfrey was allegedly involved in a drug-related love affair with Randolph Cook, who claimed they lived together for several months and did drugs. This period marked a controversial aspect of her personal life.
In 1985, before her talk show went national, Oprah Winfrey allegedly began a relationship with Haitian filmmaker Reginald Chevalier after he appeared on her show. The relationship ended when she met Stedman Graham.
On September 8, 1986, the first episode of The Oprah Winfrey Show was broadcast nationwide.
In 1986, Oprah Winfrey first announced on an episode of her TV show that she was molested by her cousin, uncle, and a family friend, starting when she was nine years old.
In 1986, Oprah Winfrey said, "'When my father took me, it changed the course of my life. He saved me. He simply knew what he wanted and expected. He would take nothing less'".
In 1986, The Oprah Winfrey Show started its national syndication broadcast from Chicago and ran for 25 years.
In 1986, Winfrey began her long-term relationship with Stedman Graham, marking a significant and enduring personal partnership in her life.
In 1987, Oprah Winfrey earned her degree from Tennessee State University, a historically black institution, after submitting her final paper.
In August 1988, Time magazine published an article on the competition between Oprah Winfrey and Phil Donahue.
In November 1988, Ms. observed that Winfrey challenged societal norms by making "fat sexy, elegant," with her wardrobe, body language, and sensuality.
In 1988, Oprah Winfrey purchased an 164-acre property in Rolling Prairie, Indiana as her weekend refuge.
In 1989, Oprah Winfrey produced and co-starred in the drama miniseries The Women of Brewster Place.
In 1989, Oprah Winfrey's half-brother Jeffrey died of AIDS-related causes.
In 1989, Winfrey was accepted into the NAACP Image Award Hall of Fame, recognizing her contributions and achievements in the field.
In 1990, Oprah Winfrey stated she felt betrayed by the family member who had sold the story of her son to the National Enquirer.
In November 1992, Winfrey became engaged to Stedman Graham, although the marriage ceremony never took place. This marked a key moment in their relationship.
From 1992 to 1994, Oprah Winfrey moderated three ABC Afterschool Specials.
In 1993, Oprah Winfrey hosted "Michael Jackson Talks ... to Oprah", a prime-time interview with Michael Jackson that became the fourth most-watched event in American television history and the most-watched interview ever, with 36.5 million viewers.
In 1993, Oprah Winfrey purchased the condos directly below her original condo in Chicago.
From 1992 to 1994, Oprah Winfrey moderated three ABC Afterschool Specials.
In 1994, Oprah Winfrey was inducted into the National Women's Hall of Fame and she finished the Marine Corps Marathon in less than four and a half hours.
Since 1994, Oprah Winfrey abandoned traditional talk-show fare for more edifying content.
On April 16, 1996, during a show about mad cow disease with Howard Lyman, Winfrey stated she was stopped cold from eating another burger, leading to a lawsuit from Texas cattlemen.
Between 1996 and 2000 Oprah Winfrey purchased a total of five condos in different development areas of Fisher Island, Florida.
Late in 1996, Winfrey introduced the Oprah's Book Club segment to her television show, creating "the Oprah Effect" by driving book sales and popularizing reading.
In April 1997, Winfrey played the therapist in "The Puppy Episode" on the sitcom Ellen, in which the character (and real-life Ellen DeGeneres) came out as a lesbian, marking a significant cultural moment.
In 1997, Randolph Cook attempted to sue Winfrey for $20 million, alleging she blocked a tell-all book about their alleged relationship. This legal action highlighted a challenging period in her personal life.
In 1997, Winfrey played a therapist on an episode of the sitcom Ellen where Ellen DeGeneres came out of the closet, leading to rumors about Winfrey's own sexuality.
In October 1998, Oprah Winfrey produced and starred in the film "Beloved," based on Toni Morrison's novel. She prepared for her role by experiencing a 24-hour simulation of slavery. Despite advertising and reviews, the film had poor box-office results.
In 1998, Oprah Winfrey began an ongoing conversation with Gary Zukav, who appeared on her television show 35 times.
In 1998, Oprah Winfrey created Oprah's Angel Network, a charity supporting charitable projects and providing grants to nonprofits worldwide. Oprah's Angel Network raised more than $80 million.
In 1998, Oprah Winfrey was named America's favorite television personality.
In 1998, 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, marking a significant milestone.
In 1998, Winfrey hosted a week-long Caribbean cruise for Maya Angelou and 150 guests to celebrate Angelou's 70th birthday, showcasing their close friendship.
In early 1998, Winfrey and Lyman were sued by Texas cattlemen for "false defamation of perishable food." On February 26, after a two-month trial in Amarillo, Texas, a jury found them not liable for damages.
Since 1998, Oprah Winfrey began 'Change Your Life TV', with most significant role as a spiritual leader.
By 2000, Winfrey's net worth reached $800 million, making her the richest African American of the 20th century.
In 2000, Oprah Winfrey purchased her friend Gayle King an estate in Greenwich, Connecticut.
In 2000, Oprah Winfrey was awarded the Spingarn Medal from the NAACP.
In 2000, Oprah Winfrey was named America's favorite television personality.
In 2001, Lavern Chatman, for whom Oprah Winfrey would later host a fundraiser in April 2014, was found liable for her role in a scheme to defraud nursing-home employees.
In 2001, Oprah Winfrey sold all five of her Fisher Island condos and purchased an estate in Montecito, California, which would become her "main home base".
Twelve days after the September 11 attacks in 2001, New York mayor Rudy Giuliani asked Oprah Winfrey to host a Prayer for America service at Yankee Stadium.
From 2002 to 2006, Oprah After the Show program on Oxygen.
In 2002, Christianity Today published an article called "The Church of O", which discussed Oprah Winfrey's influence as a spiritual leader.
In 2002, Fortune called O, the Oprah Magazine the most successful start-up ever in the industry.
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.
In 2002, Oprah Winfrey purchased her father's home in Franklin, Tennessee and a lakefront condo in Milwaukee, Wisconsin.
In 2002, Oprah Winfrey was named America's favorite television personality.
In 2002, Winfrey received the first Bob Hope Humanitarian Award at the Emmy Awards for her services to television and film.
In February 2003, Oprah Winfrey's series showing clips from people asking America not to go to war was interrupted by network broadcasts of a press conference about the case for war.
In February 2003, Oprah Winfrey's younger half-sister, Patricia, died of causes related to cocaine addiction at age 43.
A November 2003 Gallup poll estimated that 73% of American adults had a favorable view of Winfrey, indicating strong public approval.
In 2003, Oprah Winfrey listed her compound in Rolling Prairie, Indiana.
In 2003, Winfrey became the first black woman billionaire in the world, marking a historic achievement in business and wealth accumulation.
From 2004 to 2006, Winfrey was listed as the world's only black billionaire by Forbes, highlighting her unique position and financial success.
From 2004 to 2008 Oprah Winfrey also published a magazine called O At Home.
From 2004 to 2011, Winfrey was recognized by TIME as one of the most influential people, highlighting her significant impact on society.
In 2004, Oprah Winfrey became the first black person to rank among the 50 most generous Americans.
In 2004, Oprah Winfrey sold her compound in Rolling Prairie, Indiana.
In 2004, Winfrey filmed "Oprah's Christmas Kindness" in South Africa, bringing attention to children affected by poverty and AIDS. She distributed presents to 50,000 children, raising over $7 million for Oprah's Angel Network. Winfrey also invested $40 million to establish the Oprah Winfrey Leadership Academy for Girls.
On December 1, 2005, Oprah Winfrey appeared on the Late Show with David Letterman for the first time in 16 years to promote her Broadway musical, "The Color Purple." This event, which drew 13.45 million viewers, was hailed as a "television event of the decade."
Forbes named Oprah Winfrey the world's most powerful celebrity in 2005, recognizing her extensive influence and reach.
From 2003 to 2005, Oprah Winfrey acquired properties totaling 163 acres in Kula and Hana, Hawaii, as well as a penthouse apartment in Atlanta, Georgia. In 2005, she also purchased a home in Douglasville, Georgia which was gifted in 2011 to a family member.
From 2005 to 2008, the circulation of O, the Oprah Magazine declined by more than 10 percent.
In 2005, Harpo Productions released a film adaptation of Zora Neale Hurston's 1937 novel "Their Eyes Were Watching God." The made-for-television film was based upon a teleplay by Suzan-Lori Parks and starred Halle Berry.
In 2005, Kathleen Rooney's "Reading with Oprah: The Book Club that Changed America" highlighted Winfrey's use of media to promote reading and its social impact.
In 2005, Winfrey was named the greatest woman in American history as part of a public poll for The Greatest American, and ranked No. 9 overall on the list of greatest Americans.
In 2005, at the announcement of a weight-loss book co-authored with her personal trainer Bob Greene, it was said that Oprah Winfrey's undisclosed advance fee had broken the record for the world's highest book advance fee.
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 magazine, Winfrey addressed persistent rumors that she and Gayle King were gay, explaining that their close bond defies typical cultural definitions.
On September 25, 2006, Oprah & Friends began broadcasting at 11:00 am ET, from a new studio at Winfrey's Chicago headquarters. The channel broadcasts 24 hours a day, seven days a week on XM Radio Channel 156.
From 2004 to 2006, Winfrey was listed as the world's only black billionaire by Forbes, highlighting her unique position and financial success.
From 2005 to 2008, the circulation of O, the Oprah Magazine declined by more than 10 percent.
In 2006, Maureen Dowd stated in an interview that Winfrey has more credibility than the president, highlighting her significant influence in the country.
In 2006, Oprah Winfrey faced criticism from rappers Ludacris, 50 Cent, and Ice Cube, who perceived an anti-hip hop bias in her work. Ludacris claimed Winfrey edited his comments on her show and initially didn't invite him with the "Crash" cast. Winfrey responded that she opposes lyrics that "marginalize women," but appreciates artists like Kanye West.
In 2006, Oprah Winfrey purchased a co-op apartment along Lake Shore Drive in downtown Chicago, reportedly with plans to permanently move there from her prior adjoined-condo unit in Water Tower Place for the duration of her show; for reasons unknown, the property sat entirely unused until she sold it in 2012.
In 2006, Oprah Winfrey recalled controversies, including receiving hate mail for a show titled "Is War the Only Answer?"
In 2006, Oprah Winfrey sold her stake in the Oxygen network.
In 2006, Oprah Winfrey voiced Gussie the goose in "Charlotte's Web".
In 2006, Winfrey was the highest-paid television entertainer in the United States, earning an estimated $260 million, solidifying her status as a leading figure in the entertainment industry.
In 2006, after James Frey's "A Million Little Pieces" was found to contain fabrications, Winfrey confronted him on her show over the breach of trust, highlighting her commitment to honesty with her audience.
In the summer of 2006, Oprah Winfrey celebrated two decades on national TV by taking her staff and their families, totaling 1,065 people, on vacation to Hawaii as a thank you for their hard work.
Another Gallup poll in January 2007 estimated Winfrey's favorable view among American adults at 74%, marking a consistent level of public approval.
In January 2007, The Oprah Winfrey Leadership Academy for Girls opened in Henley on Klip, South Africa, with 150 pupils. Nelson Mandela praised Winfrey for her contribution.
On September 8, 2007, Oprah Winfrey held a fundraiser for Barack Obama at her Santa Barbara estate.
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 showed Winfrey's favorable view dropping to 66%, indicating a slight decrease in public approval compared to earlier polls.
On December 9, 2007, Oprah Winfrey joined Barack Obama at a rally in Columbia, South Carolina, which drew a crowd of nearly 30,000 people.
A December 2007 Fox News poll put Winfrey's favorable view at 55%, indicating a lower public approval rating compared to Gallup polls.
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.
By 2007, Oprah was often ranked as the most influential woman in the world.
Forbes named Oprah Winfrey the world's most powerful celebrity in 2007, recognizing her extensive influence and reach.
In 2007, Oprah Winfrey began to endorse the self-help program The Secret.
In 2007, Oprah Winfrey voiced Judge Bumbleton in "Bee Movie", co-starring with 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.
On January 15, 2008, Oprah Winfrey and Discovery Communications announced plans to change Discovery Health Channel into OWN: Oprah Winfrey Network.
In September 2008, Oprah Winfrey was criticized after the Drudge Report claimed she refused to have Sarah Palin on her show due to Winfrey's support for Barack Obama. Winfrey denied the report, stating there was no discussion about Palin's appearance and that she decided to avoid using her show as a platform for political candidates after publicly supporting Obama.
By 2008, Oprah Winfrey's yearly income increased to $275 million, marking continued financial success and influence in the entertainment industry.
Forbes named Oprah Winfrey the world's most powerful celebrity in 2008, recognizing her extensive influence and reach.
From 2004 to 2008 Oprah Winfrey also published a magazine called O At Home.
In 2008, Oprah Winfrey endorsed Eckhart Tolle and his book, A New Earth: Awakening to Your Life's Purpose.
In 2008, Oprah Winfrey sold her penthouse apartment in Atlanta and listed Gayle King's estate, purchasing a penthouse apartment in midtown Manhattan, New York City for Gayle King.
In 2008, Oprah Winfrey was named Person of the Year by PETA for using her fame to help animals and uncover animal cruelty.
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, Oprah Winfrey's show was airing in 140 countries internationally and seen by an estimated 46 million people in the US weekly.
In 2008, Oprah emerged as a political force with her endorsement of Barack Obama and formed her own network, the Oprah Winfrey Network (OWN).
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, Winfrey threw Maya Angelou "an extravagant 80th birthday celebration" at Donald Trump's Mar-a-Lago club in Palm Beach, Florida, demonstrating her deep affection and respect for her mentor.
In 2008, as chairman of Harpo Inc., Winfrey was named the most powerful woman in entertainment by The Hollywood Reporter, affirming her influence in the industry.
In 2008, economists estimated that Winfrey's endorsement of Obama was worth over a million votes in the Democratic primary race.
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, O, the Oprah Magazine released its best selling issue since 2006.
On November 18, 2009, Sarah Palin appeared on Oprah's show after the election, fulfilling Winfrey's promise to have her as a guest once the election was over.
In 2009, OWN: Oprah Winfrey Network's launch was delayed.
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 having Suzanne Somers on her show to discuss hormone treatments not accepted by mainstream medicine. She also faced suggestions of not being tough enough on celebrity guests or politicians she liked. A media columnist criticized Oprah's lack of follow-up questions unless an author embarrassed her by fabricating a memoir she promoted.
In 2009, Oprah Winfrey was named America's favorite television personality.
In 2009, Winfrey apologized to James Frey for the public confrontation, marking a moment of reflection and reconciliation.
In May 2010, as Oprah's show was ending, Oprah's Angel Network stopped accepting donations and was shut down, after having raised more than $80 million for charitable causes.
In September 2010, Winfrey was voted 38th in the list of "The World's 50 Most Influential Figures 2010" by the British magazine New Statesman, highlighting her global impact.
Forbes named Oprah Winfrey the world's most powerful celebrity in 2010, recognizing her extensive influence and reach.
In 2010, Bill O'Reilly of Fox News criticized Oprah Winfrey's shows about Denmark for promoting a left-wing society.
In 2010, Life magazine named Winfrey one of the 100 people who changed the world, recognizing her profound impact on society.
In 2010, Oprah Winfrey learned that she had a second half-sister.
In 2010, Oprah Winfrey narrated the US version of the BBC nature program "Life" for Discovery.
In 2010, Oprah Winfrey was among the top 50 most generous Americans.
On January 1, 2011, OWN: Oprah Winfrey Network launched.
On May 25, 2011, the series finale of The Oprah Winfrey Show aired.
From 2004 to 2011, Winfrey was recognized by TIME as one of the most influential people, highlighting her significant impact on society.
In 2011, Oprah Winfrey gifted a home in Douglasville, Georgia, which she purchased in 2005, to a family member.
In 2011, The Oprah Winfrey Show ended its national syndication broadcast from Chicago after running for 25 years.
As of 2012, Winfrey had provided over 400 scholarships to Morehouse College in Atlanta, Georgia, demonstrating her ongoing commitment to education and supporting students.
By 2012, Oprah Winfrey had given away about $400 million to educational causes.
In 2012, Oprah Winfrey sold her co-op apartment along Lake Shore Drive in downtown Chicago that she had purchased in 2006, and Gayle King's penthouse apartment in midtown Manhattan.
Forbes named Oprah Winfrey the world's most powerful celebrity in 2013, recognizing her extensive influence and reach.
In 2013, Oprah Winfrey donated $12 million to the Smithsonian's National Museum of African American History and Culture. Later in 2013, 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 significant Oscar buzz, though she was not nominated for the award.
In 2013, Oprah Winfrey was awarded the Presidential Medal of Freedom by President Barack Obama.
In April 2014, Oprah Winfrey spoke at a fundraiser for Lavern Chatman, a candidate for the U.S. House of Representatives, despite reports of Chatman's liability in a wage fraud scheme in 2001.
As of 2014, Winfrey had a net worth exceeding $2.9 billion and overtook Meg Whitman as the richest self-made woman in America, underscoring her exceptional business acumen and success.
In 2014, Winfrey was listed as one of the world's 100 most powerful women by Forbes, ranking 14th, underscoring her continued influence.
In early 2014, Oprah Winfrey listed her combined-unit Chicago duplex on the market. Later that year, Oprah came back to Telluride, Colorado to purchase a 60-acre lot with plans to build on the property. A lawsuit filed against her that year regarding trail access rights was dismissed.
In 2015, Oprah Winfrey purchased another property in Telluride, and expanded her Montecito compound with another 23-acre estate and a 44-acre 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 Winfrey selected 100 people for the SuperSoul 100 list.
In 2016, Oprah Winfrey endorsed Hillary Clinton in the election and referred to Donald Trump as a "demagogue".
In 2016, Oprah Winfrey's memoir "The Life You Want" was "indefinitely postponed".
In January 2017, Oprah Winfrey joined 60 Minutes as a special contributor.
In September 2017, Oprah Winfrey started as a special contributor on 60 Minutes.
In a 2017 interview with Vanity Fair, Winfrey explained that after losing her infant child at age 14, she did not want more children because she felt she wouldn't have been a good mother for babies.
Oprah Winfrey's memoir, "The Life You Want", was scheduled for publication in 2017, but was later postponed.
In June 2018, Apple announced a multi-year content partnership with Oprah Winfrey.
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 2018, Oprah Winfrey denied any plans to run for president, citing the nature of politics.
In 2018, Oprah Winfrey left 60 Minutes. Also in 2018, 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 Madeleine L'Engle's "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 Oprah continuing to explore impactful and relevant topics.
In the December 2020 issue, Oprah Winfrey thanked readers and acknowledged it was the magazine's "final monthly print edition".
In 2020, Oprah Winfrey faced criticism for promoting particular guests whose medical commentaries (both on her show and in the wider media) frequently lack supporting science. There were calls for her to denounce Dr. Oz.
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.
In 2021, Oprah Winfrey conducted an interview with Meghan, Duchess of Sussex, and her husband Prince Harry. This interview 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.
As of 2022, Oprah Winfrey still resides at her estate in Montecito, California, which she has called "The Promised Land".
As of 2022, Oprah Winfrey's real estate investments are estimated to total approximately $127 million, with many prominent industry outlets branding her a "tycoon".
In 2022, Oprah Winfrey endorsed John Fetterman in the Pennsylvania Senate election and Wes Moore in the Maryland gubernatorial election.
In 2022, Oprah Winfrey flipped her newly acquired Montecito properties, selling one 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 focused on voter registration and providing Black women with resources to vote.
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 2023, Oprah Winfrey purchased 870 acres of land in Maui for $6.6 million.
In 2023, Winfrey was listed as one of the world's 100 most powerful women by Forbes, ranking 31st, underscoring her continued influence.
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 one-hour show featuring interviews with tech leaders like OpenAI CEO Sam Altman and Bill Gates, exploring AI's impact on daily life.