Pop’s road is littered with the remains of artists who unsuccessfully attempted the transition from “quirky” and “fun” to “mature” – Toni Basil, Altered Images, and sadly, one of the most talented performers of the ’80s, Cyndi Lauper.

After two huge albums, a hefty number of Top Ten singles, and countless videos co-starring her manager/boyfriend, her mom and wrestling manager Captain Lou Albano, Lauper tried to jettison most of her image idiosyncrasies with her third album, A Night To Remember. Gone were the Rock & Wrestling connection, the extreme wardrobe and vocal hiccups and yelps, replaced by a sleek, almost 1940’s movie queen look and a more traditional, straight-ahead vocal approach that did not suffer any loss in quality.

And it worked – at first. Night’s first single, the Steinberg/Kelly composition “I Drove All Night” hit the Top Ten, complete with a stylish video showcasing the new, streamlined Lauper. So, it seemed the follow-up, “My First Night Without You” would be a slam-dunk to continue the streak, seeing as it was also written by Steinberg/Kelly (along with Lauper). It was even melodically familiar, ripping off the beginning of Bruce Springsteen’s “Fire” (made famous by the Pointer Sisters) and even recalling “I Drove” in places. But, for whatever reason, “My First Night” stalled in the low 60s, a chart derailing from which Lauper would never recover.

Is that fair? Take another listen to “My First Night”…it’s a heartrending affair, dancing dangerously close to the shmaltz line until you get to the middle eight and the lines:

Will I be able to sleep?
Will I lie in my bed and weep?
What if i forget
And reach for you
Will i dream about you?

It’s a genius lyric that has the protagonist in total dread that the relationship is truly over and then there’s the brutal realization that the bed is going to be a lot colder and emptier for the first time in memory. Excuse me, I need a tissue. No, I’m fine, it’s just my contacts. Leave me alone.

Lauper would not release another album until 1993’s Hat Full of Stars which basically died on arrival. She’s made a comeback of sorts as a grand dame of divas, but has yet to regain her rightful chart crown as such. Her sheer talent and likeability keeps people rooting for her, though, myself included.

“My First Night Without You” peaked at #62 on the Billboard Hot 100 in 1989.

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Cyndi Lauper

Special thanks to John Beck for the inspiration and materials!