5 best movies of Emily Osment

Her big-screen break came soon after as Gerti Giggles in the Spy Kids franchise. But it was her role as Lilly Truscott on Disney Channel’s Hannah Montana that made her famous, playing the quirky best friend to Miley Stewart across four seasons and a feature film.

Osment headlined ABC Family’s Young & Hungry and earned the Teen Choice nominations for her role as a personal chef in a chaotic tech mogul’s life. Her turn in Cyberbully showed she could take on more serious roles because she tackled themes like online harassment. She’s also appeared in shows like The Kominsky Method and Young Sheldon.

5 of the best movies of Emily Osment

1) Spy Kids 2: Island of Lost Dreams (2002)

In Spy Kids 2: Island of Lost Dreams (2002), Emily Osment plays Gerti Giggles, a spirited young spy with a quick wit and plenty of attitude. As part of the Giggles family, Gerti initially comes off as part of the competition to the Cortez siblings, Carmen and Juni. But she’s no ordinary kid—Gerti uses her tech skills and smarts to hold her own in the high-stakes world of espionage.

The film follows a mission to retrieve a stolen device capable of shutting down all technology, taking the characters to a bizarre island filled with hybrid creatures and wild inventions. Gerti’s role evolves as the true villain is revealed, and she chooses the right side, proving she’s more than just a rival.

Osment gives the character personality and humor, standing out in a cast filled with over-the-top action and imaginative gadgets. Gerti’s presence makes every scene she’s in more fun.

2) Spy Kids 3-D: Game Over (2003)

In Spy Kids 3-D: Game Over (2003), Emily Osment reprises her role as Gerti Giggles, diving into a virtual reality world full of unpredictable challenges. This time, Gerti plays a supportive role in helping Juni Cortez on his mission to save Carmen, who’s been captured inside the game.

Gerti is sharp, quick-witted, and knows when to step in, adding a bit of light-hearted fun to the team. Though she’s not in the thick of every fight, her moments bring a sense of connection and teamwork to the group as they move through dangerous game levels, battling glitches and oddball enemies.

Gerti’s sarcastic edge and her ability to stay calm in the chaos keep her memorable. While the 3-D effects and action drive the movie, Osment ensures Gerti is part of the reason the mission works.

3) Hannah Montana: The Movie (2009)

In Hannah Montana: The Movie (2009), Emily Osment steps into the role of Lilly Truscott, the kind of best friend everyone wishes they had. Lilly happens to be Miley Stewart’s confidante and she’s the keeper of her biggest secret—that Miley is living a double life as pop star Hannah Montana.

While Miley juggles the pressures of fame, Lilly acts as both her support system and occasional voice of reason, though not without a little chaos of her own.

The film takes the duo to Tennessee, where Miley is forced to reconnect with her roots. Whether she’s accidentally stealing the spotlight at a fundraiser or crafting elaborate schemes to keep Miley’s secret safe, Lilly is the glue holding everything together.

4) Cyberbully (2011)

In Cyberbully (2011), Emily Osment takes on the role of Taylor Hillridge, who is a high schooler and her life spirals after becoming a target of online bullying. The film begins with Taylor receiving a laptop as a gift, excited to join the world of social media. But what starts as a harmless dive into the digital world quickly turns dark as rumors, cruel comments, and fake profiles pile up against her.

Osment’s portrayal of Taylor is raw and honest because she plays the part of vulnerability and isolation of a teenager suffering from cyber harassment, from the initial disbelief to the overwhelming emotional toll it takes.

Osment’s performance makes the message clear: the effects of online bullying are real and deeply felt. Her work gives the film its emotional weight, making Taylor’s journey resonate with anyone who has faced online cruelty.

5) The Haunting Hour: Don’t Think About It (2007)

In The Haunting Hour: Don’t Think About It (2007), Emily Osment plays Cassie Keller, a teenager drawn to the spooky and unusual. Cassie enjoys pulling pranks and unsettling those around her. While exploring a strange shop, she finds a mysterious book with one rule: don’t read it out loud. She ignores the warning.

Reading the book unleashes the “Evil Thing,” a creature that begins terrorizing her little brother and the neighborhood. Cassie realizes she must find a way to stop it. She takes responsibility for her actions and fights to fix the problem she caused.

Osment portrays Cassie with sharp dialogue and a rebellious edge. Her performance keeps the character grounded and relatable. The movie mixes creepy moments with lighter scenes, and Osment ensures Cassie’s journey feels natural.