Madonna March Madness: Vote For The Best “Blond Ambition”-Era Videos

Nicole Sia | March 12, 2012 6:00 am

The “Blond Ambition” era of Madonna’s career — that period spanning 1986 to 1989 — was a sort of Golden Age for music videos. In just four short years, Madge released the Orwellian masterpiece “Express Yourself,” the taboo-busting “Like A Prayer” and the prototype for all of MTV’s future programming, “Papa Don’t Preach”. This division is stacked, and the battles will be close, so head below to give your favorites some love. Voting in this round, however, ends on Thursday, March 15 at 6 p.m. EST. The four victors to emerge will move on to the next round of voting in our Madonna March Madness tourney: the Sweet 16.

MATCHUP #1: “LIKE A PRAYER” VS. “WHO’S THAT GIRL” “Like A Prayer” is one of Madonna’s most controversial videos, and with good reason. With burning crosses, stigmata and interracial coupling — an incredibly taboo subject back in 1989 — Madge’s video was too hot for Pepsi to handle, and they canceled their $5 million campaign with the pop star due to protesters condemning the video. By comparison, “Who’s That Girl” is a walk in the park. A boyish, brunette Madge watches herself star in the 1987 film of the same name. Also, there’s a cartoon Madonna, a fairly uncomplicated hunt for some Egyptian treasure and a dance party with children. (We don’t expect the video to put up much of a fight.)

Madonna, “Like A Prayer”

Madonna, “Who’s That Girl”

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MATCHUP #2: “PAPA DON’T PREACH” VS. “LA ISLA BONITA” Madonna gets a pixie cut and an unexpected pregnancy in this cinematic clip (which won Best Female Video at the 1987 MTV VMAs) about mending the relationship she has with her father upon discovering she’s going to have a baby. It enters the ring against the Latin-inspired “La Isla Bonita” in which Madonna plays dual roles as a conservative, pious woman and a fiery flamenco dancer, depicting two sides of Hispanic culture and Catholicism.

Madonna, “Papa Don’t Preach”

Madonna, “La Isla Bonita”

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MATCHUP #3: “CHERISH” VS. “OPEN YOUR HEART” “Open Your Heart”, Madonna’s 1986 video in which she portrays an exotic dancer who befriends a young boy, won its place in the tourney with a staggering 70% of votes in the wildcard run-off. With one victory already in the bag, it goes up against 1989’s “Cherish.” Madonna dived right into the life of homoerotic mer-creatures in this beloved black-and-white video shot by photographer Herb Ritts — perhaps inspiring future generations of [reductive?] pop stars to fit themselves with fins.

Madonna, “Cherish”

Madonna, “Open Your Heart”[poll id=”1622″]

MATCHUP #4: “LIVE TO TELL” VS. “EXPRESS YOURSELF” In “Live To Tell,” Madonna keeps her look natural and feminine as she plays narrator in a darkened room as clips from At Close Range — starring her ex-husband Sean Penn — are shown. It’s pitted against director David Fincher’s Metropolis-inspired “Express Yourself,” the most expensive music video of its time, with a budget of $5 million. “Express Yourself” picked up three Moonmen at the 1989 MTV VMAs. Its iconography, and the song itself, continue to influence pop music to this day.

Madonna, “Live To Tell”

Madonna, “Express Yourself

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