Rank the Videos – Madonna: 1986 – 1989

Madonna AKA the Queen of Pop, kicks off her Rebel Heart tour this month, which I am attending. To lead up to the show, I’ve been looking at all of Madonna’s videos an deciding which of them are the best from each era. Previously, we looked at her earliest videos and those from the mid-80s. Now, it’s time to dive into the years that Madonna a star and even at times a controversial figure. Where will your favorite video land?

“Like a Prayer” (1989)

This is the mecca of Madonna videos. Everybody found a reason to dislike it whether it was due to a black Jesus, burning crosses, Madonna’s boobs, or the thought of sex and religion. The story line finds Madonna as a homicide witness who runs to a church wondering what her next move is going to be. Turns out the police arrested the wrong guy and Madonna questions whether or not it’s her place to correct the mistake. But references to stigmata and religion as sexual ecstasy sent viewers over the edge. The video was so controversial Pepsi pulled their previously recorded commercial with Madonna and pulled her as a sponsor. Religious groups protested against the singer for blasphemous use of religious imagery. Everyone was so obsessed with the images that most didn’t realize the message of racial harmony the singer wanted to present with the video. Whatever your feelings on it, it’s still powerful to this day. That image of her dancing in front of those burning crosses is eerie, yet memorable. Even 26 years later it remains her most groundbreaking and controversial video. This was the start of Madonna’s reign as the queen of controversy and it also found her going in a more mature direction in terms of song writing.

“Express Yourself” (1989)

Inspired by the film Metropolis, a blonde bombshell Madonna struts her stuff in various slinky outfits making her look like a vintage glamorous movie star. Later, she plays the leader of a factory where she appears in a suit and steals Michael Jackson’s go-to dance move: the crotch grab. She picks out the guy she wants, bags him, and…well, you can deduce what happened from there. With a cool neo-futuristic look and the singer looking stunning, this is another one of her top videos. It does a great job at recreating the feel and look of the movie without relying heavily on boring clips or direct references. At the time, it was the most expensive music video with a price tag of $5 million. Years later, Michael Jackson would claim that title for himself with “Scream” which cost over $10 million. The press always did say the two were in competition with each other.

“Open Your Heart” (1986)

Madonna already showed off her rampant sexuality in some of her previous clips, but she seemed to push it even further here. The video stars the singer as an exotic dancer who then puts on a titillating show for male and female onlookers. Not only does the clip pay homage to both Marlene Dietrich and Liza Minnelli, it also introduced the world to the cone bra, which would become one of Madonna’s iconic looks later on. Though the video is good and Madonna knows how to tease, some viewers weren’t happy with the clip, particularly the little boy who tries to get into the strip club. I always did find it unsettling that she kissed him on the lips at the end of the video, but I’m sure the kid was happy about it.

“Papa Don’t Preach” (1986)

Madonna changed her look again for this video where she plays a tomboyish teen who becomes pregnant. This is spliced with footage of a more glamorous looking Madonna dancing and singing the song. The idea of Madonna playing a teen at that time was a bit far fetched, but the concept was strong as she addressed the hot topic of teen pregnancy. In the end, her father comes to accept her decision, which is a bit of wishful thinking. It was at this point where it seems like more thought was put into her videos to make them mini stories, rather than just her gyrating in front of a camera (though she wouldn’t abandoned that completely).

“Oh Father” (1989)

When I started this list I was not looking forward to this video. Showing off the more mature, vulnerable side of the singer, this somber black and white clip begins with the death of a little girl’s mother. From there, we witness a tense and stressful relationship between daughter and father. This is mixed with images of Madonna looking like a 20’s movie star singing in the snow. There are also some creepy images of the gravestones in the cemetery singing along with her. This is actually a well done video, but the reason it brought me dread is one scene: when the little girl wants to give her mother a kiss while she’s lying in the casket. She see’s her mother’s lips sewn up and leaves. I first saw this when I was about five and it’s creeped the fuck out of me since. It’s so fucking unnerving especially when you don’t understand the image. This is a very personal video for the singer since it’s largely based on her life and she’s had a trying relationship with her father since her mother’s death. It’s pretty powerful and beautifully shot.

“Cherish” (1989)

The concept for this clip is pretty simple: Madonna romps around on the beach with mermen. That’s pretty much it. There are several glamour shots of the singer lounging and enjoying the water on the beach along with shots of the mermen, and one merboy, playing around in the water. It’s a pretty cute video with some sexual connotations, but that’s not a surprise considering it’s a Madonna video. The mermen actually look really cool since the fins were made by a movie studio and not by any computer technology, which would be the solution if the video were made today. What’s interesting is the video was directed by photographer Herb Ritts, who also did the video for Janet Jackson’s “Love Will Never Do (Without You),” which finds her playing on the beach. Sounds awfully familiar and they were both released in the same year? Cue the Inception music!

“La Isla Bonita” (1987)

Madonna’s always been fascinated with Hispanic culture as she’s referenced on many of her songs, but it comes out really strong on this single. In this video, Madonna plays two roles: a passive Catholic girl who prays in her room and a passionate lover who sports a traditional flamenco style dress. Both characters pine after a musician outside their window playing the Latin inspired riff. Apparently, the video symbolizes the link between Latino culture and Catholicism. It’s not her most exciting clip, but it is interesting and the fact that the song is so catchy will keep you watching just so you can sing along.

“Live to Tell” (1986)

Just when the world got used to the chunky jewelry and rubber bracelets Madonna changed her look. No longer looking like a club kid, now she looked like a classic Hollywood movie star with shoulder length blonde curls, subtle make up, and almost no jewelry. She looks gorgeous as the song comments on clips from the movie At Close Range, which starred her first husband Sean Penn. It’s not the most exciting video, but it’s notable for the beginning of her chameleon nature.

“Who’s That Girl?” (1987)

No matter how hard they try directors can’t seem to make videos that are spliced with clips from a movie interesting. At least this one features some new shots of Madonna looking particularly androgynous in a wide-brimmed Spanish hat and bolero jacket. Clips of her looking for an Egyptian treasure casket are mixed with scenes from the Who’s that Girl? movie. There are also some shots of an animated Madonna tossed in there too. While it is a little better than her earlier videos made for movies, it’s pretty boring. Not much happens, the story line is weird, and the background actors that dance with her come off as cheesy. Plus, the video was for a pretty bad movie. Best to just skip this one.

“True Blue” (1986)

This clip, which takes the song title a bit too literal, is inspired by doo-wop and the 50s. Madonna and friends are dressed sock hop style and perform cheesy dance moves in a diner and a vintage Cadillac. And yes, everything is blue. As usual Madonna looks pretty, but those dance moves and the concept are just too cheesy to find cute. It’s like they couldn’t come up with a better idea so they decided to do the 50s since the song is inspired by those cheesy doo-wop songs of the era. One writer penned it as one of her worst videos and I think he may be right.

“Dear Jessie” (1989)

This animated clip is like an unauthorized Disney movie. There are bootleg versions of the company’s most recognizable characters, like the Seven Dwarfs, Dumbo, and even Tinkerbell, who is played by a cartoon Madonna. I guess it’s a cute idea, but compared to her other videos and even her other songs, it’s just too sugary sweet. The whole thing looks and sounds like it was made for a kid’s show. The corny song, which was inspired by producer Patrick Leonard’s daughter, is enough to make you so sick that you don’t want to sit through the video at all. If you don’t want to hurl from abundant images of pink elephants, little girls, and lots of fairy dust, then you better avoid this one.

Which is your favorite video? Do you want the next part to this next month? Let me know in the comments!


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