The Ultimate Leelee Sobieski Rewatch Hub

Leelee Sobieski had a film career that was far more interesting than people give it credit for. Back in the late 90s and early 2000s, she was everywhere, and I’ll admit I’ve been a fan since about 1999 and crushed on her for a few years. Recently, I decided to sit down and actually work my way through her filmography again—either revisiting the classics or catching the ones I missed the first time around.

Around the early 2010s, she walked away from the Hollywood bubble to focus on her family, citing how overly sexualized the industry had become. She wasn’t wrong. But the work she left behind is worth a second look, especially for those of us who miss that specific era of mid-budget thrillers and dramas.

This page serves as the central hub for my Sobieski rewatch project. Below is my definitive Top 5 ranking to get things started, but check back often as I’ll be adding deep-dive reviews for each of these films, and the honorable mentions, as I finish them.

The Ultimate Leelee Sobieski Rewatch Retrospective Index:

• [Review] The Elder Son

• [Review] In A Dark Place

• [Review] Walk All Over Me

• [Review] Joy Ride

• [Review] The Glass House

• [Review] Joan of Arc

• [Review] My First Mister

Here are the five best films she actually starred or co-starred in.

The Top 5 Leelee Sobieski Films

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5. Walk All Over Me (2007)

This one tends to fly completely under the radar, which is a shame because it is a lot of fun.

Sobieski plays Alberta, a young woman who flees her small town and ends up crashing with her dominatrix sister Celene (Tricia Helfer) in Vancouver. When Alberta gets mistaken for Celene by a couple of dangerous criminals, things go sideways in a hurry.

It is a crime comedy with a good sense of humor about itself, and Sobieski is genuinely charming in it (and pretty darn hot too). The chemistry between her and Helfer works well, and the film moves along at a nice clip.

It’s not going to make anyone’s all-time list, but it is a solid, entertaining watch that deserves more attention than it got. A fun, quick watch.

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4. Joy Ride (2001)

Before Joy Ride turned into a franchise of increasingly diminishing returns, it was a tight little road trip thriller from John Dahl.

Sobieski plays Venna, the college girl dragged into a nightmare alongside Paul Walker and Steve Zahn after the two brothers make the poor decision of pranking a trucker over a CB radio. The trucker, it turns out, is not the forgiving type.

Steve Zahn is especially good here, and Walker is more than serviceable, but Sobieski holds her own just fine.

She brings enough grounded energy to the role that you actually care what happens to her especially considering the circumstances are no fault of her own. In a film like this is really all you need. It is a genuinely tense, well-crafted thriller that still holds up well.

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3. The Glass House (2001)

The critics were not kind to this one (not that they ever knew anything), and they weren’t entirely fair to it either. Sobieski plays Ruby Baker, a teenager who loses her parents in a car accident and goes to live with their glamorous friends Terry and Erin Glass (Stellan Skarsgård and Diane Lane), only to gradually figure out that something about this arrangement is very wrong.

The film belongs almost entirely to Sobieski. She is in virtually every scene, and the whole thing rises or falls on whether you buy her performance as a young woman piecing together a very dangerous puzzle while trying not to tip her hand. She pulls it off pretty well in my opinion.

Skarsgård is reliably unsettling and Diane Lane is doing interesting work in a tricky role, but it is Sobieski who makes this worth watching. Give it another shot if you wrote it off years ago or just haven’t ever watched it.

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2. Joan of Arc (1999)

This is the role that most people think of when Sobieski’s name comes up, and for good reason. Luc Besson’s CBS miniseries is a big, ambitious production — battles, sieges, the full spectacle — and Sobieski is right in the middle of all of it, playing one of the most written-about figures in history.

What she does well here is keep Joan human. It would be easy to play this as pure icon, all visions and righteousness, but Sobieski finds the doubt and the fear underneath, and that is what makes the performance stick. It earned her a Golden Globe nomination and it’s easy to see why. This is one of the better portrayals of Joan of Arc out there.

The production itself is worth noting because it punches well above its weight for a television miniseries, especially considering it was going head-to-head in the public consciousness with Luc Besson’s big-budget theatrical version starring Milla Jovovich that came out the same year.

Director Christian Duguay was primarily a television man, and the budget is what it is, but the miniseries has a scope and seriousness to it that holds up.

Sobieski was sixteen when this aired and she holds the center of all of it without ever buckling under the weight of the role. The trial sequences toward the end are especially strong; by that point, Joan has lost everything and Sobieski plays the exhaustion and the defiance at the same time in a way that sticks with you.

If you have not revisited this one, it holds up better than you might expect for a TV miniseries from the late 90s. It’s just unfortunate that it’s so hard to track down, though you can find it on YouTube.

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1. My First Mister (2001)

This is the one. My First Mister is a small, quiet film that most people seemingly have never heard of, and that is rather unfortunate because it is a great film. Sobieski plays Jennifer, or J, a misunderstood, goth teenager who strikes up an unlikely friendship with Randall, a buttoned-up, middle-aged clothing store manager played by Albert Brooks.

The premise sounds odd, and it is, but the film makes it work very well. The relationship between Jennifer and Randall is completely believable because both actors commit to it fully, and director Christine Lahti handles the tonal shifts with a steady hand.

I thought the ending could have been better, and that the last act fell into a cliché that screams “of course.” But still a wonderful movie with a good heart.

Sobieski is flat-out great here. The film should have found a wider audience. If you have not seen it, fix that. On a side note, it’s rather amazing how much Leelee, who gets compared so much to Helen Hunt, looks like modern-day Rhea Ripley in the beginning of the movie.

My First Mister capped off a great year for Sobieksi, easily her best year as an actress, considering three of the five on this list came out in 2001.

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Honorable Mentions

A few films that did not quite crack the top five but are worth knowing about.

Deep Impact (1998) is the better of the two “asteroid heading for Earth” movies from that summer, and Sobieski has a supporting role as the young friend and love interest of Elijah Wood’s character. She doesn’t have a ton of screen time, but she makes an impression, and the film itself holds up pretty well as a disaster movie with more on its mind than just the spectacle. This one couldn’t be ranked because she isn’t a star of it, but it is a great movie nonetheless.

The Elder Son (2006) is a comedy-drama based on a play by Alexander Vampilov, and it’s one of the more unusual entries in her filmography. Sobieski plays Natasha opposite Mikhail Baryshnikov, in a slow-burn story about two strangers who talk their way into a man’s apartment on a cold night and end up tangled in his family’s life. It is a quiet, character-driven film and not for everyone, but if that kind of thing is your speed it is worth seeking out.

In a Dark Place (2006) is a loose adaptation of Henry James’ The Turn of the Screw with Sobieski in the lead as a teacher who takes a job at a remote estate and starts to believe the children in her care are being influenced by something sinister. The film has its issues and the reviews were rough, but Sobieski commits fully to it and there are genuinely unsettling moments in there. Worth a watch for fans of gothic horror even if it does not fully come together.

Sobieski has a small supporting role in Never Been Kissed (1999) as Aldys, the nerdy, academically gifted outcast who Drew Barrymore’s undercover reporter character befriends while posing as a high school student. It is not a large role but it is a warm and likable one, and Sobieski plays the awkward sincerity of the character well without ever making her the butt of the joke. The film itself is a lot of fun and holds up better than you might expect, and Aldys is a big part of why the high school scenes work as well as they do. Worth a mention even if the role is too small to crack the main list.

On the other end of the spectrum, Night Train (2009) is a disappointment, and actually I’d say the film is down right terrible. The setup is not bad — Sobieski, Danny Glover, and Steve Zahn are strangers on a train who find a mysterious box on a dead passenger and start making very bad decisions about what to do with it. It should work. It does not. The film squanders a decent cast and an interesting premise by going nowhere interesting with either of them, and by the time it wraps up you will have stopped caring well before it bothered to explain itself. Skip it, it’s dumb to an almost infuriating degree.

Here on Earth (2000) is simply bad. Sobieski is stuck playing Samantha, the small-town girl caught in a love triangle between her dependable boyfriend (Josh Hartnett) and a wealthy douche (Chris Klein) who rolls into town and turns everything upside down. The script is loaded with every cliché the genre has to offer, the third act goes to maudlin places that feel completely unearned, and the whole thing plays like a checklist of early 2000s teen drama tropes rather than an actual story. Sobieski tries. She always tries. But there is only so much you can do when the material is this thin. It doesn’t help the film any that Sobieski’s character is unlikable. It’s like A Walk to Remember, without the heart of a likeable character, and you’re glad she dies in the end.

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Have a Sobieski film you think deserved a spot on this list? Drop it in the comments.