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Flashback Friday: You can't talk about hotties of the 90s without Winona Ryder

Sep. 20, 2013by: Droz
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When discussion of the best hotties of the 90s comes up, somewhere in that list you have to mention Winona Ryder. It could be argued that she owned that decade, both for her persistent pop culture status and for the way she reflected the general state of discontent inherent with many a Gen-X'er. Everyone was pissed off or disturbed for no good reason back in those days. Nobody felt good about anything, which was what kept bands like Tool and Nine Inch Nails rolling in cash. It was appropriate then that our cinema sweethearts felt like we did. Winona specialized in playing the outcast, the misfit, the stifled and frustrated youth who didn't know about or refused to acknowledge both convention and any sense of how beautiful she was. Everybody loved her for that too, which made her the big name she was back in those days. Of course, her name and career weren't the only big things she owned.

The fact that we never got a decent look at these was one of the great tragedies of the 90s.

Winona always liked to portray herself as one of those disaffected youths she played in the movies, but life as a movie star with tons of cash and engagements to the likes of Johnny Depp made that seem difficult to believe. That is, until the details of her secret life of shoplifting were exposed in the early 2000s following her arrest for supposedly nabbing $5000 in designer clothes. Quite the unfortunate time for Winona and her fans, especially when the subsequent trial turned into a media circus. The really sad part is that Winona has never recovered from that time. Famous drug addicts, sex addicts, alcoholics, even outright criminals have managed to redeem themselves and restore careers. For some reason Winona's penchant for the 5-finger discounts still burdens her. But at least she still shows up from time to time, though mostly just supporting roles. Will we ever see Winona make a big splash again? You never know. We can still enjoy the good ole days though, some of which is represented below.

Click on each photo to enlarge!

Source: Moviehotties

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3:38PM on 09/20/2013
Been a fan of hers since Beetlejuice and is the only reason I watched Mr. Deeds and S1m0ne.
Been a fan of hers since Beetlejuice and is the only reason I watched Mr. Deeds and S1m0ne.
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+16
7:10PM on 09/20/2013
Supremely unique.

Supremely unique.

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9:33PM on 09/20/2013
So cute in those two photos in the pink dress, and a lovely tummy in that last shot! Great selection of photos.
So cute in those two photos in the pink dress, and a lovely tummy in that last shot! Great selection of photos.
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10:37PM on 09/20/2013

A gorgeous woman back in the day

I suspect Winona has more than a few emotional issues (other than anxiety and depression, which she's copped to) which has hurt her career. It also doesn't help that she's fallen into the same trap as many other actresses who hit their thirties: there just aren't that many great roles in Hollywood for women of that age, if your name isn't Meryl Streep.
I suspect Winona has more than a few emotional issues (other than anxiety and depression, which she's copped to) which has hurt her career. It also doesn't help that she's fallen into the same trap as many other actresses who hit their thirties: there just aren't that many great roles in Hollywood for women of that age, if your name isn't Meryl Streep.
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+14
11:25PM on 09/20/2013
Hot and cute then and still very hot and cute now.
Hot and cute then and still very hot and cute now.
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+10
12:44PM on 09/21/2013

She's very good in The Iceman

And she still looks young. Hard to imagine She's actually 3 years older than Michael Shannon.
And she still looks young. Hard to imagine She's actually 3 years older than Michael Shannon.
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+11
12:54PM on 09/21/2013

Winona Forever

I remember when Johnny had that tattoo. She's still so pretty. She's a fantastic actress and has made so many wonderful films. I didn't realize she was in The Iceman. Yet another reason other than Shannon I need to get to watching that one. It would be great if she made a turn around I think her fan base would welcome her back easily.
I remember when Johnny had that tattoo. She's still so pretty. She's a fantastic actress and has made so many wonderful films. I didn't realize she was in The Iceman. Yet another reason other than Shannon I need to get to watching that one. It would be great if she made a turn around I think her fan base would welcome her back easily.
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-15
6:02PM on 09/21/2013
I agree with Stratburst. She still looks great but she really looks and acts like she has some serious emotional problems. If she took pictures like any of these I don't think she'd look cute or intense as much as disturbed (still beautiful but seriously off!).
I agree with Stratburst. She still looks great but she really looks and acts like she has some serious emotional problems. If she took pictures like any of these I don't think she'd look cute or intense as much as disturbed (still beautiful but seriously off!).
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