Oprah Winfrey Trivia
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50 free Oprah Winfrey trivia questions with answers — entertainment quiz, new questions added Aug 2026.
This Oprah Winfrey trivia quiz covers the whole arc, from a rural Mississippi childhood with a grandmother who taught her to read before three to the most influential woman in media. It starts with the name that was misspelled on her birth certificate, the potato-sack dresses, the move to Milwaukee, the father in Nashville who 'saved' her, the WVOL radio job in high school and the anchor desk she reached at 19. The middle of the quiz is about the career: the Baltimore demotion, People Are Talking, the takeover of AM Chicago that overtook Donahue within months, Roger Ebert's advice to syndicate, Harpo Productions, The Color Purple and Beloved, the Michael Jackson interview watched by 36.5 million, the Book Club, the James Frey confrontation, the Texas cattlemen's lawsuit, the launch of Dr. Phil and Dr. Oz, OWN and the 2011 finale. The final stretch takes in Stedman Graham and Gayle King, the Montecito estate, the Marine Corps Marathon, the Obama endorsement worth a million primary votes, the South African academy, and the Presidential Medal of Freedom. Difficulty runs from easy to expert and is shown on every question. Every answer was checked against a reference page and each question carries its citation. Try our Barack Obama and David Letterman quizzes next.
30 of 50 questions with answers and explanations. Play the quiz
Q 01How was Oprah's first name spelled on her birth certificate?
Orpah
It came from the biblical Orpah in the Book of Ruth; constant mispronunciation made 'Oprah' stick.
Q 02In which Mississippi town was Winfrey born in 1954?
Kosciusko
Kosciusko: her mother went north to look for work soon after the birth, leaving Winfrey on her grandmother's farm there for her first six years.
Q 03As a small child Winfrey was mocked for wearing clothes made of what?
Potato sacks
Potato sacks: her grandmother Hattie Mae was too poor to buy clothes, yet she taught Winfrey to read before the girl was three.
Q 04What childhood nickname did Winfrey earn for her recitations?
The Preacher
The Preacher: by the age of three she was reciting Bible verses in church, and at home she practised interviewing her corncob doll and the crows on the fence.
Q 05At six, Winfrey moved to an inner-city neighbourhood in which city?
Milwaukee
Milwaukee: she joined her mother Vernita Lee, whose long hours as a housemaid left little time for Oprah, and as a troubled teenager she was sent on to her father.
Q 06What was the Nashville trade of Winfrey's father Vernon, who she has said 'saved' her?
Barber
Barber: Vernon Winfrey ran a barbershop and sat on the city council, and his strict rules turned his daughter into an honours student.
Q 07Which beauty pageant did Winfrey win as a teenager in the early 1970s?
Miss Black Tennessee
Miss Black Tennessee: she won it while reading the news part-time at WVOL, the radio station that hired her after she won its Miss Fire Prevention title.
Q 08Winfrey's scholarship to Tennessee State University came from winning what?
An oratory contest
An oratory contest: public speaking paid for college, yet she left one credit short for a TV job and finished her degree only after she was famous.
Q 09Which future TV host covered the same Nashville stories at a rival station while Winfrey anchored at WLAC-TV?
John Tesh
John Tesh, later the long-time host of Entertainment Tonight, has confirmed that the two rival cub reporters also dated for a short time.
Q 10In 1976 Winfrey moved to which city's WJZ-TV to co-anchor the six o'clock news?
Baltimore
Baltimore: WJZ-TV removed her from the anchor desk in 1977, and the demotion led to the talk show People Are Talking, where she found the format that suited her.
Q 11Which low-rated WLS-TV morning show did Winfrey take over in January 1984?
AM Chicago
AM Chicago: within months her warm style took the half-hour show from last place to first in its slot, and it was renamed The Oprah Winfrey Show.
Q 12Which film critic persuaded Winfrey to sign a syndication deal with King World?
Roger Ebert
Roger Ebert: on a dinner date he worked out on a napkin how much more a syndicated show would earn her than his own did, and she took the advice.
Q 13At a 2004 season premiere, what did Winfrey give every member of her studio audience?
A new car
A new car: all 276 guests got a Pontiac G6, donated by General Motors as a publicity splash rather than paid for by Winfrey.
Q 21Which rapper told GQ that Winfrey gave him a 'hard time' when he appeared on her show with the cast of Crash?
Ludacris
Ludacris said she lectured him about his lyrics and edited his comments out of the episode; Winfrey answered that she objects only to rap that marginalises women.
Q 22Which duchess sat down with Winfrey for a prime-time CBS interview in March 2021?
Meghan, Duchess of Sussex
Meghan, Duchess of Sussex: she and Prince Harry said a royal had asked how dark their son's skin would be, and the Queen replied that 'some recollections may vary'.
Q 23Winfrey's Oscar-nominated role in The Color Purple (1985) was which character?
Sofia
Q 14Whose programme did Winfrey's show displace as America's number-one daytime talk show?
Phil Donahue's
Phil Donahue's: within months of arriving in Chicago her last-placed local show was out-drawing his there, before she beat him nationwide.
Q 15Through which company did Winfrey take ownership of her talk show?
Harpo Productions
Harpo Productions, 'Oprah' spelled backwards, was set up to make the screen projects she wanted to see produced, and it went on to take over her show from ABC.
Q 16Winfrey co-founded which women's cable network?
Oxygen
Oxygen: she co-founded the channel in the late 1990s, then moved on to launch a network under her own name, OWN, in 2011.
Q 17OWN, the Oprah Winfrey Network, was created by rebranding which existing channel?
Discovery Health
Discovery Health: the 2008 plan called for a 2009 relaunch, but the rebranded channel did not reach air until January 1, 2011.
Q 18Which actor jumped on Winfrey's couch during a 2005 interview to show how in love he was?
Tom Cruise
Tom Cruise: he hopped onto the sofa and dropped to one knee over new girlfriend Katie Holmes, a scene that set Hollywood talking and was widely parodied.
Q 19Winfrey's 1993 prime-time interview with which star became the most-watched television interview in US history?
Michael Jackson
Michael Jackson: at his Neverland Ranch he told her that the skin disorder vitiligo, not bleaching, had lightened his skin.
Q 20Winfrey's December 2005 appearance with which late-night host ended a rumoured 16-year feud?
David Letterman
David Letterman: after the taping he walked her across the street to the Broadway opening of her musical The Color Purple, and the truce drew his biggest audience since 1994.
Sofia: Winfrey had never acted before producer Quincy Jones cast her, yet the debut earned her both Oscar and Golden Globe nominations.
Q 24To prepare for Beloved (1998), Winfrey underwent a simulation of what?
The experience of slavery
The experience of slavery: she was tied up, blindfolded and left alone in the woods to prepare for playing Sethe, yet the film she produced flopped at the box office.
Q 25Winfrey voiced Eudora in which Disney film?
The Princess and the Frog
The Princess and the Frog: Disney first asked Winfrey to advise on how the film handled race, and then cast her as the heroine's mother.
Q 26Which character did Winfrey play in the 2018 film A Wrinkle in Time?
Mrs. Which
Mrs. Which is the oldest and wisest of the three guides, and director Ava DuVernay did not have to think twice about the casting: she had Winfrey in mind from the start.
Q 27In 1988 Winfrey celebrated losing 67 pounds by bringing what onto her stage?
A wagon of fat
A wagon of fat: she had gone four months on a liquid diet without solid food, yet many of the pounds came back once she returned to real food.
Q 28Fortune called which Winfrey venture 'the most successful start-up ever in the industry' in 2002?
O, The Oprah Magazine
The magazine's final monthly print edition was December 2020.
Q 29Which athlete admitted doping to Winfrey in 2013 after years of denials?
Lance Armstrong
Lance Armstrong: cycling had stripped his seven Tour de France titles months earlier, and he told her he had used banned drugs for every one of those wins.
Q 30Winfrey calls her main home in Montecito, California, by what name?
The Promised Land
The Promised Land: she has kept adding to the estate, even buying neighbour Jeff Bridges's retreat, until it covered nearly 70 acres.