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1990

Madge really sold the period garb. It's lush.

Also present: heaving bosoms.

This lasted a split second but the screen cap is amazing.

Sinead O'Connor

And then you compare that with Sinead. Actually, that probably made for a good show: Someone who gives you a visual feast, and then someone who really dials you in on her vocals.

Aerosmith

I just really was NOT paying attention to ANYTHING that Aerosmith was doing back then. I don't know WHY! Had I known that hat was in play...

Wilson Phillips

Chynna looks one tray shy of being a cigarette girl at a theater.

New Edition

They had already split up by this point, and Bell Biv Devoe was on its way, but this was a big reunion. I really hoped they'd have used their sleeve pocket to whip out prop hankies or gloves, but I guess they were JUST sleeve pockets. (This played fitfully for me, but seriously, David Silver was SO inspired by New Edition.)

Justine Bateman

That is a high-fashion lead apron, not a dress.

Brad Pitt

OH HI THERE.

Khrystyne Haje

Ah, the halcyon days of Head of the Class.

Sherilyn Fenn and Michael Ontkean

AND of Twin Peaks.

Shadoe Stevens and Beverly Cunningham

They are still married, and HOLY CATS, does their child -- actress Amber Stevens -- look like her mother.

Living Colour

The neckerchief and overalls are a feast, but the surrealist hellscape of that shirt next to them is going to give me nightmares.

Kim Basinger

Sandy from Grease is a very tired aesthetic.

Arsenio Hall

He is like a ringmaster here. Also, this photo reminds me of how Chris Rock would play him on SNL and use a super long pointer-finger extension.

Bobby Brown

Chaps are not great. Pants that WISH they were chaps are arguably worse. At least chaps have COMMITTED.

Mike Patton

So. This sagging fanny pack looks HILARIOUSLY like he might just be wearing plaid nut-huggers.

MC Hammer

This is a man who is extremely confident about his nipples.

Michael Hutchence

That is a JAZZY SHIRT. I kind of enjoy it? He must have performed barefoot or something, because he is not shod here...

Kylie and Michael Hutchence

... but here he is fully booted, and with Kylie, who looks like she is ready for an Austin Powers flick.

Rachel Ward

"Michael Hutchence GETS ME."

Vince Neil

"I was not the worst-dressed person in this slideshow! HELL YEAH!"

The 1990 VMAs Also Had an Iconic Madonna Moment
WIGS! SKIRTS!

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