I just saw that last week on cable. It was beyond terrible. Nigh unwatchable, in fact, and this coming from a guy who watches tons of godawful movies. (She was the only reason I watched it in the first place.)
She was in a “brat pack” with Lindsay Lohan for a while years ago. Keep in mind, this was very brief so it only made a few mentions in a magazine or website. She’s been making wise career choices.
There was a thread two years ago on the subject of promising actresses whose careers never took off. It seems now Leelee Sobieski would be a perfect example of one of those.
Sobieski’s problem was the same as other actors and actresses in her position: she never got the part that would’ve taken her fame to the next level (e.g., female lead in a high-grossing blockbuster and/or an Oscar-nominated role). You have a limited time to get one of these and, right now, it looks as though Sobieski’s window of opportunity is closing.
You could argue this was due to Sobieski’s lack of talent (even though from what I’ve seen her in, she seemed at least fairly competent) but luck is an even bigger factor. When an actor or actress signs on for a role, they do so without being 100% sure the project will click or not. Remember Goldman’s Rule: NOBODY KNOWS ANYTHING. In her case, 88 Minutes and the remake of **The Wicker Man **might’ve actually looked good going in.
[QUOTE=Cat Fight]
It’s difficult to remember more than a few of her movies, but even tougher to recall any scandals, stars she dated or details about her personal life. She didn’t play the game. She had a kid with her partner instead of getting drunk and flashing her bits. Gossip column exposure may be less important as she ages, if she continue to has a career, but is pretty crucial for an actress in her early 20s.
[/QUOTE]
Actually, playing the game the way you described is a double-edged sword. Sure, the general film-going public might notice you more but it can adversely affect your credibility as an actress and render you unemployable (e.g.,Lindsey Lohan).
I don’t remember hearing that at all. I’ve always thought her biggest claim to fame was the Helen Hunt resemblence.
Well she went to Brown, fell in love, moved to New York, had a child and from this interview seems happy to be a nobody.
“I think I’m kind of off the radar now,” she says. “If I do get back on the radar … I don’t know if I want that. I love being able to sit outside at a café with my baby and relax and enjoy the sun.”
Aha…that’s code for “Secret Dominatrix to the Stars” if I ever heard it. 
This was pretty much my reaction to the thread title. I do not recognize the name Leelee Sobieski, and upon checking her IMDb entry I felt I only “recognized” her face in the sense that she looks a lot like Helen Hunt. Looking through her filmography then the only thing she’s ever been in that I saw was 1999’s Never Been Kissed, and I couldn’t tell you who she played in that. Since then she hasn’t even been in anything I wanted to see. (And I see a fair number of movies each year.) Ms. Sobieski has been working steadily, which is more than plenty of actors manage, but I don’t see any reason why she should be “above” doing a minor role on a TV series.
Did we ever find out who the Jenna Moran mentioned in the OP was supposed to be? IMDb doesn’t give any actress of that name or anything close.
Possibly the actress Jena Malone.
She was a main character. Remember how Drew Barrymore’s character made the one highschool friend? That was her.
I remember that character, but I thought at the time that she was played by Julia Stiles. Looking at the IMDb I see that Ms. Stiles wasn’t in Never Been Kissed at all, but that’s what I thought.
Now I wonder, who were the other It Girls from 1999-2001 and what are they doing today?
And I wonder what the careers of Emma Stone, Carey Mulligan and Kristen Stewart will be like in 2021.
As best I recall: Neve Campbell, Christina Ricci, Kirsten Dunst, Kate Hudson, Thora Birch, Mena Suvari, Julia Stiles, Amy Smart and Katie Holmes.
Neve Campbell- Apparently still pulling in roles, though nothing really “star worthy”. Mostly TV stuff.
Christina Ricci- Darling of the indie scene, still cranking out a decent amount of work. Mostly indy movies, with a recent burst of voice work for games such.
Kirsten Dunst-Spiderman. Pays the bills quite well, I’m sure. Looks like she does quite a bit of work, but mostly on stuff nobody has seen, or at least I haven’t really heard of.
Kate Hudson- Had a kid, so slowed down for a while. Seems to be trying her hand at directing and producing the last few years, and has a handful of stuff in production at the moment as an actress.
Thora Birch- another one who seems to have done some indy stuff, and appears to have some stuff coming out soon, but I have heard that her dad/manager is VERY tough to work with. And creepy.
Mena Suvari- Appears to mostly be doing TV stuff lately. And voice work on the Kingdom Hearts series, which I did not know. Huh.
Julia Stiles- Appears to be doing a decent amount of work, most recently in a recurring role on Dexter. Not as prolific as the rest of the list, she does appear to be taking a swing at the bi leagues with a role in, and producing, “The Bell Jar”.
Amy Smart- again, not a lot here. Quite a bit of TV work, including multiple runs on Robot Chicken. Not sure what that might mean.
Katie Holmes- Mrs. Tom Cruise, who has slowed way down on her work, but appears to be jumping back into things. Lots of rumors about this one, but nothing concrete.
(All sources are IMDB, or my constant browsing of celeb gossip sites. Does not include broadway or stage work, which I understand Julia Stiles and Katie Holmes have both done, at least a little bit)