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100

What song did Madonna dedicate to her daughter Lourdes Leon?

"Little Star" (1998)

100

Which artist/friend did Madonna feature on her 1994 Album "Bedtime Stories"?

Björk 

100

What controversial symbol did Madonna utilize during her 2006 Confessions tour?

The Crucifix

100

Which Italian actor was Madonna's home originally meant for?

Rudolph Valentino

100

What film did Madonna act in while 4 months pregnant?

"Evita"

200

What was the name of the fashion brand launched by Madonna and her daughter Lourdes Leon?

Material Girl

200

Who was her maid of honor in her wedding to Guy Ritchie?

Gwyneth Paltrow

200

What was the name of the 1980 stage play Madonna wrote and starred in?

"In Artificial Light"

200

Which artists/bands were Madonna's main inspirations?

Blondie and The Pretenders

200

What film did Madonna star in that released in 1985, despite having been filmed prior to Madonna's rise to fame in 1979?

"A Certain Sacrifice"

300

Where did Madonna's two adopted children, Esther and Stella come from?

Malawi

300

Who is one of Madonna's oldest friends?

Former makeup artist, Debbie Mazar
300

What was her signature look/style while performing "Express Yourself" and "Vogue"

A cone-shaped bra

300

Which famous dancer did Madonna study under?

Martha Graham

300

Which films did Madonna receive the Worst Actress award for?

"Shanghai Surprise" (1986), and "Who's That Girl?" (1987)

400

Which actor is Madonna distantly related to?

Mark Wahlberg

400

Which friend of Madonna's designed her wedding dress in her wedding to Guy Ritchie?

Stella McCartney

400

Who designed Madonna's costumes during the 1990 Blonde Ambition Tour ( including her signature cone-bra )

Jean-Paul Gaultier

400

What does Madonna describe as one of her pet peeves?

People who are ignorant or assumptive

400

What role did Madonna campaign for that eventually ended up going to Salma Hayek?

Frida Kahlo

500

How many children does Madonna have?

Six ( Rocco, David, Mercy, Stella, Estere, and Lourdes )

500

Which popular 2000's singer is Madonna friends with?

Britney Spears

500

Which old hollywood celebrities was the song "Vogue" a tribute to?

Greta Garbo, Marilyn Monroe, Marlene Dietrich, Joe DiMaggio, Marlon Brando, James Dean, Grace Kelly, Jean Harlow, Gene Kelly, Fred Astaire, Ginger Rogers, Rita Hayworth, Lauren Bacall, Katharine Hepburn, Lana Turner, and Bette Davis.

500

What form of media does Madonna dislike, banning her children from watching?

Television

500

Which one of Madonna's films was considered a "box-office disaster" ?

"Shanghai Surprise" (1986)
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