I don't think it was her best (most attractive) look TBH.

Like A Prayer-era Madonna was better, especially because she really is a natural brunette.

.

Who's That Girl?-era Madonna was a parody of True Blue-era Madonna.

THIS BITCH HAS NEVER BEEN PRETTY

She had that younger fresh face, still a tad of baby fat on her here and there. She never needed makeup back then, nor do most young women. I think her eyes sparkled from pure (blond) ambition in everything she did. She doesn't need to be a good actress to have been captivating in Who's That Girl or even Desperately Seeking Susan.

uPtoWnNY said:

Who's That Girl is actually my favorite Madonna movie it's alot of fun.

80s pop flashback: "Who's That Girl" by Madonna (1987)

madonna who's that girl - YouTube

alphastreet said:

where is Hollywood? Banned?

Madonna - Hollywood (Offi... - YouTube

SoulAlive said:

SoulAlive said:

SoulAlive said:

alphastreet said:

where is Hollywood? Banned?

Madonna - Hollywood (Offi... - YouTube

Banned by who and why, exactly? That's silly.

alphastreet said:

SoulAlive said:

Madonna - Hollywood (Offi... - YouTube

I meant the poster here who thought she was prettier than vanity

Pretty is subjective. Vanity never did anything for me. She's all torso with short legs. She's always been weird-looking. Different strokes. At that age my stroke went to Madonna by a mile.

FUNKNROLL said:

This topic came up recently with friends. In the 80s, she was marketed as a sex symbol but I can’t recall any male high school friends who thought she was hot. She definitely wasn’t the pinup girl poster in young mens bedrooms like Heather Locklear, etc. Maybe that was her genius. We were all told she was hot; but really, she’s not.

How I remember things most of my 13 years old friends thought she was pretty cool and attractive when she started out. But there were many better looking female singers and actresses around at that time. And a few years later Madonna lost her appeal to me altogether, I became indifferent. On the other hand, I certainly wouldn't have kicked her out of my bed if she were interested.

Love that movie, so funny and cute! Not a fan of the look though.

FUNKNROLL said:

This topic came up recently with friends. In the 80s, she was marketed as a sex symbol but I can’t recall any male high school friends who thought she was hot. She definitely wasn’t the pinup girl poster in young mens bedrooms like Heather Locklear, etc. Maybe that was her genius. We were all told she was hot; but really, she’s not.

I don't necessarily believe she was marketed as a sex symbol. Sexy maybe. She did that herself. She very much had an idea of what she wanted to do and be protrayed.

Also, sexy back then was quite different. It feels more like she was sexually open, and in the 80s that was provocation enough to get attention. She was on boy's walls, but there were so many new sex symbols and certainly marketed in a bigger way that she was easily lost in the barage of blond haired beauties.