Why did she never really make it?

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I guess it has something to do with the fact that she doesn't play the "Hollywood game": she often says in interviews that she doesn't go to parties, and she doesn't flirt, she feels uninspired by traditional Hollywood movies...

here are some quotes from her:
"I didn't like anything. It was crazy, I was very picky. In other words, I didn't take advantage of what was happening necessarily then. But they also have a way of putting you in a category. I wasn't into playing the Hollywood game. I only responded to certain things."
"I don’t get considered for a lot of those big fat movies. The studios have their list of five actresses and whether they’re right or wrong for a role doesn’t matter. It’s how much money their last movie made. Not that I necessarily want to do them anyway. Because there’s very few that are big budget that have any substance or any depth or any integrity."

After "Twin Peaks", she wanted to avoid typecasting but the roles that were offered to her were variations of Audrey Horne, so she said no to several roles.

She also got unlucky, as many of her projects didn't end up happening, like the "Barbarella" remake (1993) by Roger Vadim, the "Gilmore Girls" spin-off (2003) by Amy Sherman Palladino, and other TV shows like "Prey" (1997), "Blind Men" (2001), "Birds of Prey" (2002), "Mr. Ed" (2004), or "Three Moons Over Milford" (2006).

As for a recent picture, here's one from 2005:
http://content9.flixster.com/photo/10/49/04/10490495_gal.jpg

Thanks for the info qylecoop. And two good quotes to offer a clear insight into the gorgeous Fenn's mind there.
It taught me not to judge a book by its cover because when you look at Fenn and also some of the erotic 'thrillers' she's done you'd think she'd be an UTTER FLIRT and love to be asked to do big movies acting opposite handsome leading men.

And yet she hasn't and fair play to her. I can't help thinking she's rather thrown her career away though. Why couldn't she do a Depp and do a quirky low budget film followed by a big budget one to pay the bills and raise the profile and perhaps get a few awards on the way?

She's now perilously close to playing the 'mother' role in films and when that happens its usually goodbye to any interesting meaty acting roles...

And I must admit she looked better with dyed blonde hair. She now looks too much like an older Charlize Theron (which is good but not really distinctive anymore sadly).

I think it's her voice. She's personable yes. But her voice is distinct. Character actor.

Also, she definitely isn't typical shallow hollywood.

https://www.quora.com/Why-didn-t-Sherilyn-Fenn-become-a-bigger-star/answer/Jon-Mixon-1

I was never that impressed by her acting. Not that she was bad, but she never stood out, either. A competent actress who was very good looking.