Madonna Trivia
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59 free Madonna trivia questions with answers — music quiz, new questions added Sep 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 59 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 04Madonna dropped out of which school's dance program?
The University of Michigan
The University of Michigan: it gave her a full dance scholarship, but she dropped out and moved to New York to pursue dance.
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, based in an abandoned Queens synagogue, did Madonna sing and play drums?
Breakfast Club
Breakfast Club: she joined her boyfriend Dan Gilroy's band as its drummer, later sang lead, then left to start bands of her own.
Q 07What was Madonna's debut single, released in October 1982?
Everybody
Everybody: DJ Mark Kamins slipped her demo into his Danceteria set, and when the dance floor liked it he helped her land a record deal.
Q 08Which Sire Records president signed Madonna in 1982?
Seymour Stein
Seymour Stein: he heard her demo on a Walkman in his hospital bed, then had her come to the hospital and agreed a deal on the spot.
Q 09Which 'Jellybean' Benitez-produced track was Madonna's breakthrough from her 1983 debut?
Holiday
Holiday: its writers Curtis Hudson and Lisa Stevens first recorded it for their group Pure Energy, but their label said it wasn't a hit.
Q 10Which Quentin Tarantino film opens with its gangsters in a diner debating what Madonna's 'Like a Virgin' is about?
Reservoir Dogs
Reservoir Dogs: Tarantino's own Mr. Brown insists the song is about sex, while Madonna said she was singing about feeling brand-new.
Q 11Which disco hitmaker produced Madonna's 1984 album Like a Virgin?
Nile Rodgers
Nile Rodgers: he expected 'Material Girl' to be the big hit, not the title track, but 'Like a Virgin' became her first Hot 100 number one.
Q 12At a 1984 awards show, Madonna performed 'Like a Virgin' after appearing on top of what?
A giant wedding cake
A giant wedding cake: when one of her stilettos slipped off on the way down, she dove to the floor and rolled around as if she'd planned it.
Q 13Whom did Madonna marry on her 27th birthday in 1985?
Sean Penn
Sean Penn: she wrote the song 'True Blue' for him.
Q 21Under what title was the 1991 documentary Truth or Dare released outside North America?
In Bed with Madonna
In Bed with Madonna: her then-boyfriend Warren Beatty is caught on camera mocking her refusal to stop filming.
Q 22What was the name of Madonna's character in Dick Tracy (1990)?
Breathless Mahoney
Breathless Mahoney: one of the character's lines in the film inspired Madonna's top-ten hit 'Hanky Panky'.
Q 23With whom did Madonna write and produce 'Vogue'?
Shep Pettibone
Shep Pettibone: he made it on a $5,000 budget as a B-side, until executives heard it and released it as a single.
Q 14Which 1985 film song gave Madonna her first UK number-one single?
Into the Groove
Into the Groove: it played in a dance scene in Desperately Seeking Susan, yet it wasn't on any album when it came out.
Q 15Who played the bored housewife opposite Madonna's bohemian drifter in Desperately Seeking Susan?
Rosanna Arquette
Rosanna Arquette: she had the leading role, yet she was overshadowed by her co-star's soaring pop fame.
Q 16At which 1985 benefit concert did Madonna joke about her newly published nude photos?
Live Aid
Live Aid: she told the Philadelphia crowd she wasn't taking anything off that day, weeks after Playboy and Penthouse ran the pictures.
Q 17In 1988 Madonna made her Broadway debut in which play?
Speed-the-Plow
Speed-the-Plow: some critics were cruel, but The New York Times's Frank Rich praised her 'intelligent, scrupulously disciplined comic acting'.
Q 18'Like a Prayer' premiered in a 1989 commercial for which company, which then dropped her over the video?
Pepsi
Pepsi: facing boycott calls from religious groups, it dropped her ads and ended its plans to sponsor her world tour.
Q 19Which superstar duets with Madonna on 'Love Song', from her 1989 album Like a Prayer?
Prince
Prince: he also played the distorted guitar that opens 'Like a Prayer', though he went uncredited.
Q 20Which French designer created the costumes, including the cone bra, for the 1990 Blond Ambition World Tour?
Jean Paul Gaultier
Jean Paul Gaultier: the tour's provocations drew a papal call for a boycott in Italy, and Toronto police threatened to arrest her.
Q 24Which network banned the 'Justify My Love' video in 1990?
MTV
MTV: after it refused to air the video, Madonna went on ABC's Nightline to defend it.
Q 25Which 1990 Madonna greatest-hits album introduced the new songs 'Justify My Love' and 'Rescue Me'?
The Immaculate Collection
The Immaculate Collection: its new single 'Justify My Love' was adapted from a love letter Ingrid Chavez had written to Lenny Kravitz.
Q 26Which of these acts was signed to Madonna's Maverick label?
Alanis Morissette
Alanis Morissette: despite hits from acts like her, Maverick sued Warner in 2004, claiming mismanagement had cost it millions.
Q 27Which fashion photographer shot Madonna's 1992 coffee-table book Sex?
Steven Meisel
Steven Meisel: despite the outrage, Sex sold 150,000 copies on its first day in the US alone.
Q 28To which rapper, then her boyfriend, did Madonna propose in the early 1990s?
Vanilla Ice
Vanilla Ice: he appeared in photos in her book Sex, though he later said he hadn't wanted to be part of it.
Q 29During her notorious 1994 Late Show appearance, what did Madonna hand David Letterman?
A pair of her underwear
A pair of her underwear: her profane appearance drew a backlash, which she answered with the song 'Human Nature'.
Q 30Which ballad, written with Babyface, is Madonna's longest-running Billboard Hot 100 number one?
Take a Bow
Take a Bow: when Babyface played her the bare bones of the track at his home studio, she took to it at once.