1986 Madonna in concert.

I’m certain you won’t be able to predict Madonna’s most watched music video on YouTube. It would’ve been my 50th guess. Madonna had so many iconic music videos during MTV’s early days when they still played music videos (here’s why they don’t). In fact, some of Madonna’s most memorable music videos, at least to me, aren’t even in her top 20 on the Madonna YouTube channel.

Some of Madonna’s 80s megahits like “Dress You Up,” “Open Your Heart,” “Borderline,” “Express Yourself,” “Lucky Star,” “Ray of Light,” “Cherish,” and “Who’s That Girl” didn’t make the cut on this list Madonna’s 20 most-viewed music videos on YouTube!

  • #20: True Blue

    Madonna’s 1986 hit written about her then husband Sean Penn.

  • #19: Celebration

    This was a song recorded for Madonna’s third greatest hits album. This music video is the remixed version by Benny Benassi.

  • #18: Crazy For You

    This song was recorded for the 80s movie “Vision Quest.”

  • #17: Into the Groove

    Another soundtrack hit, this one was featured in “Desperately Seeking Susan.” This is the unofficial official music video since one was never shot.

  • #16: Sorry

    Madonna busts out the roller skates!

  • #15: The Power of Good-Bye

    Entertainment Tonight said recording the video for this one was emotional for Madonna since the lyrics of a breakup hit close to home.

  • #14: Girl Gone Wild

    You might not remember this song from Madonna’s 2012 album MDNA.

  • #13: Give Me All Your Luvin'

    Nicki Minaj being a part of this video could explain the YouTube views on this one.

  • #12: Give It 2 Me

    Madonna used her look from an Elle magazine cover photo shoot as the inspiration for this music video.

  • #11: Live To Tell

    Madonna toned down her look for this one.

  • #10: Like a Virgin

    This one was shot in Venice and New York and cost $150,000 – a LOT at the time.

  • #9: Material Girl

    Channeling her inner Marilyn Monroe…

  • #8: Vogue

    Filmed in black and white as Madonna paid tribute to Hollywood actors and actresses of years gone by.

  • #7: Frozen

    Witchy Madonna!

  • #6: 4 Minutes

    No wardrobe malfunctions in this duet with Justin Timberlake.

  • #5: Papa Don't Preach

    No Danny Aiello is not her real life father.

  • #4: Like a Prayer

    This one ruffled lots of feathers back in the 80s. It led to a Pepsi boycott.

  • #3: B*tch I'm Madonna

    Another one that features Nicki Minaj.

  • #2: Hung Up

    The music video pays tribute to John Travolta and his movies.

  • #1: La Isla Bonita

    And here it is, her most viewed music video! It’s one of those 80s hits that many tend to forget. See if you can spot Benicio Del Toro. He’s one of the extras paid $150 to be in the video.

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