2005–11: Charlie and the Chocolate Factory and Astro Boy
Highmore at the San Diego Comic-Con International, 23 July 2009
In 2005, he portrayed the main role of Charlie Bucket in the musical fantasy film Charlie and the Chocolate Factory, adapted from the book of the same name by Roald Dahl. He was reportedly recommended by co-star Johnny Depp, whom Highmore had worked with in Finding Neverland; Depp had been impressed by the young actor's performance and thus put his name forward for the role. Highmore did not see the original 1971 version of the film, and decided not to see it until he was done filming so his portrayal of Charlie would not be influenced. For his role, he again won Critics' Choice Movie Award for Best Young Performer and was awarded the Satellite Award for Outstanding New Talent. Highmore also lent his voice to the film's accompanying video game of the same name.
He next appeared as a young Max Skinner (Russell Crowe) in the comedy-drama film A Good Year, which was released in the UK on 27 October 2006. Also in 2006, he began portraying protagonist Arthur Montgomery in the live-action/animated fantasy adventure film Arthur and the Invisibles, released on 13 December 2006. Two sequels followed: Arthur and the Revenge of Maltazard (2009) and Arthur 3: The War of the Two Worlds (2010). For the third film and the trilogy's accompanying video game, Highmore provided voice acting.In 2007, he lent his voice to the adventure fantasy film The Golden Compass (2007) and its video game of the same name. He then portrayed the title character in the drama film August Rush (2007), alongside Keri Russell, Jonathan Rhys Meyers, and Robin Williams. The story follows a musical prodigy as he searches for his birth parents. This film received a wide release on 21 November 2007.
Highmore next starred in the dual role of American twins Simon and Jared Grace, alongside Sarah Bolger as their sister Mallory, in the fantasy adventure film The Spiderwick Chronicles (2008), based on the popular children's stories of the same name by Tony DiTerlizzi. The film also had a video game, The Spiderwick Chronicles, in which Highmore reprised the characters of Simon and Jared in a voice role. That same year, he provided voice acting for the role of Little Jack in the animated film A Fox's Tale (2008). In 2009, Highmore voiced the lead character in the animated film Astro Boy, and provided his voice to its accompanying video game, Astro Boy: The Video Game.He then played the main role in Toast, a BBC autobiographical film about chef Nigel Slater, which was aired on 30 December 2010. The miniseries marked the second time Highmore has worked with Helena Bonham Carter.Also in 2010, he starred as Hally Ballard, opposite Ving Rhames, in the drama film Master Harold...and the Boys, based on the play of the same name by Athol Fugard. The following year, he co-starred alongside Emma Roberts in the romantic comedy-drama The Art of Getting By (2011).