Leelee Sobieski holding a camera

 

Uprising 2001

The film begins with the German invasion of Poland in 1939, leading to the forced relocation of Polish Jews into the Warsaw Ghetto. The Jewish council, or Judenrat, led by Adam Czerniaków, faces impossible moral dilemmas as they are ordered to send Jews to extermination camps like Treblinka. As deportations escalate, a group of young Jewish leaders, including Mordechai Anielewicz and Yitzhak Zuckerman, organize the Jewish Combat Organization (ZOB) and prepare for armed resistance. The uprising begins in April 1943, with fighters using homemade weapons and defensive bunkers to hold off thousands of German troops. ​⁠

Cast 

 • Leelee Sobieski as Tosia Altman

 • Hank Azaria as Mordechai Anielewicz

 • David Schwimmer as Yitzhak Zuckerman

 • Jon Voight as Maj. Gen. Jürgen Stroop

 • Donald Sutherland as Adam Czerniaków

 • Stephen Moyer as Simcha “Kazik” Rotem

 • Sadie Frost as Zivia Lubetkin

 • Radha Mitchell as Mira Fuchrer

 • Mili Avital as Devorah Baron

Just a smoking hot Leelee

 

“Walk All Over Me” (2007)

Leelee Sobieski plays Alberta, a small-town woman who moves to the city and gets entangled in a dangerous situation after impersonating her roommate, a professional dominatrix. The film features scenes where Sobieski wears military-inspired and uniform-like outfits, which match your collage description. The story blends crime, drama, and dark comedy, set against a backdrop of mistaken identity and escalating stakes. ​

My First Mister (2001) is a coming-of-age drama about an unlikely friendship between a teenage girl and a middle-aged man

 Synopsis 

“My First Mister” follows Jennifer, a 17-year-old goth girl who feels alienated from her family and peers. She meets Randall Harris, a reserved, lonely man in his late 40s who manages a clothing store. Their relationship begins when Jennifer applies for a job at Randall’s store, and despite their differences, they form a deep, platonic bond. The film explores themes of loneliness, acceptance, and the transformative power of friendship as both characters help each other confront personal pain and grow emotionally. The story is tender, sometimes quirky, and ultimately uplifting, focusing on how two outsiders find connection and meaning in each other’s lives.

My Take 

“My First Mister” is a quietly powerful film that avoids clichés about age-gap relationships by focusing on genuine emotional intimacy rather than romance. The performances—especially by Leelee Sobieski and Albert Brooks—bring authenticity and vulnerability to their characters. The movie’s strength lies in its honest portrayal of loneliness and the unexpected ways people can change each other’s lives. It’s a film that values empathy, self-discovery, and the courage to open up, even when it’s uncomfortable. If you appreciate stories about personal growth and unconventional friendships, “My First Mister” is worth watching.

Leelee Sobieski as Venna Wilcox in 'Joy Ride' (2001)

In the 2001 thriller film "Joy Ride," Leelee Sobieski plays Venna Wilcox, a smart and down-to-earth college student who becomes the object of affection for the film's protagonist, Lewis Thomas (played by Paul Walker).

The film's plot is set in motion when Lewis, a college freshman, decides to take a cross-country road trip to pick up Venna, a long-time friend he secretly has a crush on. His romantic plans take a dark turn when he and his mischievous older brother, Fuller (played by Steve Zahn), play a cruel prank on a psychopathic truck driver known as "Rusty Nail" over a CB radio.

Venna is introduced to the film after the brothers have already started their terrifying ordeal with Rusty Nail. As Lewis and Fuller's prank spirals out of control and the unseen trucker begins a deadly game of cat and mouse, Venna gets unwittingly caught in the middle of the brothers' dangerous situation. She becomes a central figure in the film's climax, as Rusty Nail's vengeful pursuit intensifies, and the trio must fight for their lives.

Leelee Sobieski as Anna Veigh in "In a Dark Place" (2006)

 In the 2006 horror-thriller film "In a Dark Place," Leelee Sobieski stars as Anna Veigh, a young art teacher and therapist who takes a job as a nanny for two orphaned children on a remote country estate.

The film is a modern adaptation of Henry James's classic gothic novella, "The Turn of the Screw." Anna is hired to care for the children, Miles and Flora, but soon begins to suspect that the house is haunted by the ghosts of the previous governess and her lover. As Anna's grip on reality becomes increasingly fragile, she questions whether the supernatural occurrences are real or a manifestation of her own psychological trauma.

The movie explores themes of childhood abuse and a deteriorating mental state, with Sobieski's character, Anna, grappling with her own past as she tries to protect the children. The film's ambiguity leaves the audience to decide if the ghosts are real or a product of Anna's troubled mind.

Leelee Sobieski was born in New York City on June 10, 1983

Leelee Sobieski was born in New York City on June 10, 1983. Her mother was a film producer and screenwriter, while her father was a French painter and former actor. Sobieski grew up dividing her time between Manhattan and the south of France.

As a child, she took flamenco lessons and rode horses. She was discovered by a casting agent at the age of 11 in her school's cafeteria, which led to her first audition for a role in the movie "Interview with the Vampire." Though the part ultimately went to another actress, this marked the beginning of her acting career. She went on to appear in TV movies and series, and rose to fame in her mid-teens with her role in the 1998 film "Deep Impact."

Trivia: Leelee Sobieski

Here’s some fascinating trivia about Leelee Sobieski that even many of her fans might not know:

1. She Turned Down Harvard for Acting

Leelee was accepted into Harvard University but deferred enrollment to pursue acting. She later admitted in interviews that she never ended up attending because her career took off with roles in Deep Impact (1998) and Eyes Wide Shut (1999).

2. She Almost Played Queen Amidala in Star Wars

Sobieski was one of the top contenders for Padmé Amidala in Star Wars: Episode I – The Phantom Menace (1999). The role ultimately went to Natalie Portman, but George Lucas reportedly liked Sobieski’s regal presence and even considered her for another Star Wars project years later.

3. She Quit Acting Because of Typecasting

After gaining fame in the late '90s and early 2000s, Sobieski grew frustrated with being offered the same "innocent girl in peril" roles (The Glass House, Joy Ride). She stepped back from Hollywood in the mid-2010s to focus on painting (her artwork has been exhibited in galleries) and raising her family.

4. She Was Discovered in a Grocery Store

At just 12 years old, Sobieski was spotted by a talent agent while shopping with her mother in a New York grocery store. Within a year, she landed her breakout role in A Horse for Danny (1995).

5. She’s Fluent in French & Studied Philosophy

Sobieski’s father is Polish, and her mother is American, but she spent much of her childhood in France. She speaks fluent French and even studied philosophy in her spare time during her acting career.

6. She Played Joan of Arc Twice

Sobieski portrayed Joan of Arc in both a 1999 CBS miniseries (for which she earned an Emmy and Golden Globe nomination) and in The Adventures of Young Indiana Jones (earlier in her career). She called it a "spiritual experience."

7. She Rejected Blockbuster Roles

Besides Star Wars, she turned down major franchises like Spider-Man (the role of Mary Jane Watson went to Kirsten Dunst) and The Lord of the Rings (she was considered for Éowyn).

8. She’s a Published Poet

In addition to painting, Sobieski has written poetry, some of which was published in literary journals under a pseudonym.

 

Leelee Sobieski as Ruby Baker in The Glass House (2001)

Here’s an intriguing and lesser-known story about Leelee Sobieski’s role as Ruby Baker in The Glass House (2001):

The Real-Life Fear Factor

During filming, Leelee Sobieski developed a genuine fear of driving after performing the movie’s intense car crash scene. The sequence, where Ruby and her brother (played by Trevor Morgan) are nearly run off the road by their sinister guardians, was shot practically with stunt drivers and rigged vehicles. Sobieski, who was only 17 at the time, admitted in an interview that the realism of the stunt left her shaken—so much so that she avoided driving for months afterward.

A Hidden Tribute

Director Daniel Sackheim incorporated subtle visual homages to classic thrillers like The Shining and Psycho in The Glass House, but one of the most obscure references is tied to Sobieski herself. The glass-walled Malibu house used for filming (which was a real, privately owned property) had its interiors modified to include eerie, reflective surfaces that distorted characters’ faces—a nod to Sobieski’s earlier role in Eyes Wide Shut (1999), where mirrors played a symbolic role.

The Alternate Ending That Never Was

Originally, the script included a darker ending where Ruby’s fate was left ambiguous, implying that she might still be in danger. Test audiences reacted negatively, so the studio reshot it to give a more definitive resolution. However, Sobieski reportedly preferred the original version, feeling it was truer to the film’s suspenseful tone.

 

Four sides of Leelee

The image of Leelee Sobieski is a collage of four different scenes featuring her. Each scene is a close-up and medium shot, focusing on her face and upper body. The scenes vary in setting and her apparent emotional state, suggesting different moments or contexts.

Leelee Sobieski as Ruby Baker in The Glass House (2001)

 

Leelee Sobieski as Ruby Baker in The Glass House (2001) – A Throwback to Early 2000s Hollywood Magic!

If you were flipping through channels or hanging at the movie theater back in 2001, chances are you caught a glimpse of Leelee Sobieski shining bright in The Glass House . She played Ruby Baker — smart, sassy, and seriously unforgettable — and totally stole the show with her fierce energy and flawless style.

But before she slipped into those iconic early aughts vibes on screen, Sobieski was already making waves in Hollywood. Born in NYC on June 10, 1983, she started acting as a kid and fast became one of Tinseltown’s most promising young stars. You might remember her from the epic TV movie Joan of Arc (1999), where she played the legendary warrior in a role that earned her major praise and put her name on the map.

From there? It was full speed ahead. She lit up the screen in Never Been Kissed , helped save the planet in Deep Impact , and kept us all hooked in The Glass House . With every role, she brought this cool mix of elegance and edge — like she belonged on both a red carpet and in a teen drama at the same time.

But here's the twist: instead of riding the fame train forever, Sobieski made a bold move. In the early 2010s, she said “peace out” to Hollywood and stepped away from the spotlight. Why? To focus on what really mattered to her — family, art, design, and just living life on her own terms. No drama, no headlines — just doing her thing.

So while we don’t see her gracing the covers of magazines anymore, we’ll always have those classic roles that remind us how awesome she was (and still is!). Leelee Sobieski wasn’t just another pretty face in the 2000s — she was a legit standout star who chose her own adventure. And honestly? That’s kind of inspiring.

More photos of Leelee Sobieski

The Life and (Almost) Disappearance of Leelee Sobieski

Unusual Name: Her full name is Liliane Rudabet Gloria Elsveta Sobieski. Talk about a mouthful!   

Early Fame: She gained significant recognition at a young age, appearing in films like "Deep Impact" and "Eyes Wide Shut" while still in her teens. 

Retired from Acting: Leelee Sobieski retired from acting in 2012 to focus on her family and pursue her passion for art.   

Artistic Pursuits: After leaving acting, she dedicated herself to visual arts, exploring various mediums like painting and ceramics.   

Family Ties: Her mother is a film producer, and her father is a painter.