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60 free Madonna trivia questions with answers — music quiz, new questions added Aug 2026.
This Madonna trivia quiz follows the Queen of Pop from Bay City, Michigan and a $35 arrival in New York to the 1.6-million-strong free concert on Copacabana Beach that closed the Celebration Tour. In between: drumming for Breakfast Club, the wedding-cake VMA performance, the Pepsi ad the Vatican killed, Jean Paul Gaultier's cone bra, the banned Justify My Love video, the Sex book, Evita's Golden Globe, William Orbit and Ray of Light, ABBA clearing a sample for Hung Up, the Super Bowl halftime show and Madame X's Lisbon roots. The questions cover the songs, albums, films, tours, marriages, children, business ventures and controversies, with easy openers for casual listeners and hard ones for anyone who can name the Sire Records boss who signed her or the play in which she made her Broadway debut. Every answer was checked against Wikipedia's articles on Madonna, her albums, singles, films and tours, and each question quotes the sentence that supports it.
30 of 60 questions with answers and explanations. Play the quiz
Q 01Where in Michigan was Madonna born in 1958?
Bay City
She grew up in the Detroit suburbs of Pontiac and Rochester Hills; her father was an engineer for Chrysler Defense.
Q 02Because she shared her mother's first name, what did Madonna's family call her as a child?
Little Nonnie
Her mother, an X-ray technician, died of breast cancer when Madonna was five.
Q 03What confirmation name did Madonna take in the Catholic Church in 1966?
Veronica
Her father gave her a quarter for every A on her report card, and she was a straight-A student and cheerleader at Rochester Adams High School.
Q 04According to Madonna, how much money did she have when she arrived in New York City in 1978?
$35
It was the first time she had ever flown or taken a taxi; she had left a dance scholarship at the University of Michigan.
Q 05At which famous New York restaurant did the young Madonna work as a hatcheck girl?
The Russian Tea Room
She also ran an elevator at Terrace on the Park and studied under Martha Graham and at the Alvin Ailey school.
Q 06For which band, rehearsing in an abandoned Queens synagogue, did Madonna sing and play drums and guitar?
Breakfast Club
Boyfriend Dan Gilroy and his brother lived there; she later formed Emmy with drummer Stephen Bray, a longtime writing partner.
Q 07What was Madonna's debut single, released in October 1982?
Everybody
Danceteria DJ Mark Kamins produced it after she talked her way into a meeting with Sire Records.
Q 08Which Sire Records president signed Madonna to a two-single deal in 1982?
Seymour Stein
Sire was a Warner Bros. subsidiary; at the time she was living in Jean-Michel Basquiat's SoHo loft.
Q 09Which 'Jellybean' Benitez-produced track was Madonna's breakthrough from her 1983 debut?
Holiday
She had been unhappy with Reggie Lucas's production and brought Benitez in to remix most of the record.
Q 10Who wrote 'Like a Virgin'?
Billy Steinberg and Tom Kelly
Steinberg came up with the lyric while driving a pickup around his father's vineyards; the pair also wrote 'True Colors' and 'Eternal Flame'.
Q 11Which Chic guitarist produced the Like a Virgin album?
Nile Rodgers
He brought Chic bandmates Bernard Edwards and Tony Thompson as the rhythm section; the album was the first by a woman to sell five million copies in the US.
Q 12At the first MTV VMAs in 1984, Madonna performed 'Like a Virgin' after appearing on top of what?
A giant wedding cake
Wearing a wedding gown and white gloves, she rolled around the stage; MTV News later called it one of pop's most iconic performances.
Q 13Whom did Madonna marry on her 27th birthday in 1985?
Sean Penn
They met while filming the 'Material Girl' video; True Blue was dedicated to him, and she filed for divorce in January 1989.
Q 21Under what title was the 1991 documentary Truth or Dare released outside North America?
In Bed with Madonna
Alek Keshishian's film became the highest-grossing documentary ever, a record it held for eleven years.
Q 22What was the name of Madonna's character in Dick Tracy (1990)?
Breathless Mahoney
Warren Beatty directed and starred; the accompanying album I'm Breathless produced 'Vogue'.
Q 23With whom did Madonna write and produce 'Vogue'?
Shep Pettibone
She saw dancers voguing at the Sound Factory; the song topped charts in more than 30 countries.
Q 14Which song from Desperately Seeking Susan gave Madonna her first UK number-one single?
Into the Groove
'Crazy for You', from Vision Quest, was her second US number one that same year.
Q 15Who played the bored housewife opposite Madonna's bohemian drifter in Desperately Seeking Susan?
Rosanna Arquette
Susan Seidelman directed; New York Times critic Vincent Canby named it one of the ten best films of 1985.
Q 16How much was Madonna reportedly paid per session for her 1978 nude art-model photos?
$25
The pictures later sold for up to $100,000; she remained unapologetic about them.
Q 17In 1988 Madonna made her Broadway debut in which play?
Speed-the-Plow
It ran at the Royale Theatre from May to August; her later West End outing, Up for Grabs, was panned in 2002.
Q 18'Like a Prayer' premiered in a 1989 commercial for which company, which then dropped her over the video?
Pepsi
The video's burning crosses and stigmata drew Vatican condemnation and boycott calls, so the sponsor pulled the ad and ended the deal.
Q 19Which superstar co-wrote and co-produced 'Like a Prayer' with Madonna, Leonard and Bray?
Prince
The album spent six weeks at number one, her longest, and Rolling Stone called hers 'one of the most compelling voices of the Eighties'.
Q 20Which French designer created the costumes, including the cone bra, for the 1990 Blond Ambition World Tour?
Jean Paul Gaultier
She recruited him with a handwritten letter; Pope John Paul II urged a boycott of the tour and Toronto police threatened to arrest her.
Q 24Which network banned the 'Justify My Love' video in 1990?
MTV
The controversy helped push the song, one of two new tracks on The Immaculate Collection, to number one.
Q 25About how many copies has The Immaculate Collection sold, the best-selling compilation by a solo artist?
30 million
It arrived in November 1990 with 'Justify My Love' and 'Rescue Me' as new songs.
Q 26Which of these acts was signed to Madonna's Maverick label?
Alanis Morissette
Maverick launched in 1992 with a $60 million Time Warner advance; Michelle Branch was another signing.
Q 27Which fashion photographer shot Madonna's 1992 coffee-table book Sex?
Steven Meisel
It topped the New York Times bestseller list despite savage reviews, and its backlash overshadowed the album Erotica.
Q 28To which rapper did Madonna propose during the Erotica era?
Vanilla Ice
They split after Sex came out; he said he had been included in the book without consent.
Q 29During her notorious 1994 Late Show appearance, what did Madonna hand David Letterman?
A pair of her underwear
She also swore enough to require broadcast censorship, and urged him to smell the item.
Q 30How many weeks did 'Take a Bow', Madonna's longest-running Hot 100 number one, spend on top?
Seven
It came from Bedtime Stories, the softer 1994 album meant to win back public favor.