It's very rare for former child actors to maintain steady work upon entering adulthood, but luckily for Haley Joel Osment, that hasn't been much of a problem. From working on indie Kevin Smith films to playing the villain of HBO's Entourage movie to constant video game voiceovers, the Oscar-nominated actor has still managed to keep himself busy.
Despite his moderate success as an adult, there's no doubt that Osment is much more well-known for the work he did during his childhood. Like most actors, he had hits and misses, but his successes were far more memorable than most other child actors of the '90s and early 2000s.
Pay It Forward (2000)- 7.2
Based on the book of the same name by Catherine Ryan Hyde, Pay It Forward is one of those films that most people can only handle watching once. In the film, Osment plays a young boy who launches the "pay it forward" movement, where an individual repays an act of goodwill from a stranger with one of their own.
With Leslie Dixon's script, and powerful performances from Osment, Kevin Spacey, and Helen Hunt, the film is an emotional roller-coaster. Osment stands out as a bullied adolescent who strikes up a reluctant friendship with Spacey's reclusive character. While the expectations of the viewers are initially shattered by the film's tragically bittersweet ending, its message of how one person can truly make a difference is one that can never be forgotten.
AI: Artificial Intelligence (2001)- 7.2
In one of his most underrated films, Steven Spielberg puts a futuristic sci-fi spin on the classic tale of Pinocchio in AI: Artificial Intelligence. Osment portrays David, a robot child who ventures out into the world with the hope of becoming a real human boy to win the love of the mother who had programmed him. The film was initially conceived by Stanley Kubrick before his passing, and Spielberg took to completing Kubrick's vision to honor his memory.
Kubrick originally imagined having the character of David be a CGI creation, as he was doubtful that any child actor could successfully pull off the role. With Osment's exceptional performance and Spielberg's direction, many would like to think that Kubrick had been proven wrong. Osment expertly conveys David's inner turmoil while also showing that the boy isn't quite as human as his flesh and blood family.
Secondhand Lions (2003)- 7.5
Written and directed by co-writer of The Iron Giant, Tim McCandles, Secondhand Lions is one of Osment's more overlooked films. It tells the story of Walter, a young boy who is left by his mother to live with his two great uncles on their farm in Texas. Through their eccentric nature, stories of their adventurous youth, and with a lioness living on their land, the two uncles form an unexpected and heartfelt bond with the boy.
Alongside fellow Oscar nominees Michael Caine and Robert Duvall playing his uncles, Osment manages to deliver a performance just as enduring and entertaining as they do. While this extremely wholesome dramedy isn't often mentioned in discussions of the best films of Duvall's career, or even Osment's and Caine's, it's certainly an emotionally comforting feel-good film that's worth checking out at least once.
The Sixth Sense (1999)- 8.1
The 3rd film directed by M. Night Shyamalan and the film that earned Osment an Oscar nomination for Best Supporting Actor, The Sixth Sense marked the dawning of a new kind of psychological and supernatural thriller. The film tells the story of a child psychologist whose patient, Cole Sear, possesses the ability to see and talk to the spirits of the dead.
The film has long been discussed and analyzed for its themes of trauma and loss as well for having one of Shyamalan's best twist endings. With Osment's chilling and iconic performance, it's easy to see why and how he earned an Oscar nomination at just 11 years old. The young actor conveys Cole's many conflicting emotions, often in just one scene: terror, sadness, fear, and enduring love for his mother. Osment's emotional conversation with Toni Collette at the film's climax is masterful in how the child star can equally carry a complicated scene with an experienced actor. It's a landmark child performance, one that still holds up today.
Forrest Gump (1994)- 8.8
One of the most iconic and recognizable films ever made, and one of the best films of the 1990s, Robert Zemeckis' classic film Forrest Gump was the film debut of Osment, who was only 6 years old at the time of its release. As the film that took home 6 Oscars in 1995, including Best Picture, it doesn't get much better for a young child actor than to have it as one of the very first jobs on their resume.
Osment plays the son of Forrest and Jenny, and while his character doesn't show up until the final minutes of the film, it's a memorable appearance nonetheless. Osment does a good job at portraying a pint-sized version of Forrest: innocent, naive, and curious about the life that happens around him.
Kingdom Hearts (2002)- 9.2
It might be surprising to some that Osment's most highest-rated project isn't a film or television series, but a video game. In Kingdom Hearts, the first in a series of collaborations between The Walt Disney Company and Square Enix, Osment voices the game's lead character, Sora; a teenage boy who travels throughout multiple worlds of Disney films, all while fighting demonic creatures known as "Heartless" with both Donald Duck and Goofy by his side.
The game became a worldwide phenomenon upon its release and sparked a series of sequels that continue on to this very day. With its rich lore, nostalgia-driven world-building, and highly entertaining gameplay, it holds a very special place in video game history. It's also quite admirable just how devoted Osment is to the character of Sora. He started voicing the character at age 12 and has continued to do so for nearly two decades up to age 31 in 2019 with the release Kingdom Hearts III (which, despite its title, is actually the 11th game in the franchise).