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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
Her mother Vernita Lee was a teenage housemaid; her father Vernon was a coal miner who later served on the city council.
Q 03As a small child Winfrey was mocked for wearing dresses made of what?
Potato sacks
Her grandmother Hattie Mae was that poor, yet taught her to read before she was three.
Q 04What nickname did the young Winfrey earn at her grandmother's church?
The Preacher
She could recite Bible verses on demand; she also 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
Her mother worked long hours as a maid; by 1962 she was struggling and sent Oprah to her father in Nashville for a time.
Q 06Winfrey has said her father Vernon 'saved' her. What was his trade in Nashville?
Barber
He was strict but encouraging; she became an honours student and finished second in the nation in dramatic interpretation.
Q 07At 17, Winfrey won which beauty pageant?
Miss Black Tennessee
The same year the black radio station WVOL hired her to read the news part-time.
Q 08Winfrey's full scholarship to Tennessee State University came from winning what?
An oratory contest
She studied communication but did not hand in her final paper until 1987, when she was already famous.
Q 09Which future TV host covered the same Nashville stories at a rival station while Winfrey anchored at WLAC-TV?
John Tesh
The two also dated in the 1970s; biographer Kitty Kelley says the interracial pressure ended it.
Q 10In 1976 Winfrey moved to which city's WJZ-TV to co-anchor the six o'clock news?
Baltimore
She was removed from the anchor desk in 1977 and later paired with Richard Sher on the talk show People Are Talking.
Q 11Which low-rated WLS-TV morning show did Winfrey take over in January 1984?
AM Chicago
General manager Dennis Swanson hired her; within months it had gone from last place to beating Donahue.
Q 12Which film critic persuaded Winfrey to sign a syndication deal with King World?
Roger Ebert
He predicted she would earn 40 times what his own show made; they also briefly dated.
Q 13On what date was The Oprah Winfrey Show first broadcast nationwide?
September 8, 1986
It doubled Donahue's national audience and became the number-one daytime talk show.
Q 21Which rapper told GQ in 2006 that Winfrey gave him a 'hard time' about his lyrics?
Ludacris
Winfrey said she opposed lyrics that marginalise women but enjoyed some artists, including Kanye West.
Q 22Winfrey and Prince Harry's 2021 interview was with which member of the royal family?
Meghan, Duchess of Sussex
It was broadcast globally and became one of the most discussed interviews of the decade.
Q 23Winfrey's Oscar-nominated role in The Color Purple (1985) was which character?
Sofia
She later produced the Broadway musical of Alice Walker's novel, which opened in late 2005.
Q 14Whose talk show did Winfrey displace as America's number-one daytime programme?
Phil Donahue's
Time called hers 'the talk show as a group therapy session'; her 'rapport talk' was contrasted with his 'report talk'.
Q 15What is the name of Winfrey's production company?
Harpo Productions
It is 'Oprah' spelled backwards and produced Dr. Phil, Rachael Ray and The Dr. Oz Show.
Q 16Winfrey co-founded which women's cable network?
Oxygen
It first carried Oprah After the Show from 2002 to 2006, before she sold her stake.
Q 17OWN, the Oprah Winfrey Network, was created by rebranding which existing channel?
Discovery Health
Announced in January 2008 for a 2009 launch, it finally went on air on January 1, 2011.
Q 18When did the series finale of The Oprah Winfrey Show air?
May 25, 2011
The show ran 25 seasons in national syndication.
Q 19Winfrey's 1993 interview with which star drew 36.5 million viewers, the most-watched ever?
Michael Jackson
It ranked as the fourth most-watched event in American television history.
Q 20Winfrey's December 2005 appearance with which late-night host ended a rumoured 16-year feud?
David Letterman
She was promoting The Color Purple musical; Letterman drew 13.45 million viewers, his biggest audience in 11 years.
Q 24To prepare for Beloved (1998), Winfrey underwent a 24-hour simulation of what?
The experience of slavery
She was tied up, blindfolded and left alone in the woods; the film lost about $30 million despite two episodes of her show devoted to it.
Q 25Winfrey voiced Eudora, the mother of Tiana, in which Disney film?
The Princess and the Frog
She also voiced Gussie the goose in Charlotte's Web and Judge Bumbleton in Bee Movie.
Q 26Which character did Winfrey play in the 2018 film A Wrinkle in Time?
Mrs. Which
Reese Witherspoon and Mindy Kaling played the other two Mrs. Ws.
Q 27Winfrey's advance for a 2005 weight-loss book reportedly broke the record held by whose autobiography?
Bill Clinton's
The book was co-written with her personal trainer Bob Greene.
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 29Winfrey's 2006 satellite radio deal with XM was worth how much over three years?
$55,000,000
Her contract required her on air just 30 minutes a week, 39 weeks a year.
Q 30Winfrey calls her main home in Montecito, California, by what name?
The Promised Land
Bought in 2001, the compound has grown to about 70 contiguous acres, including land bought from Jeff Bridges.