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Pine rose to prominence for his roles in the romantic comedies The Princess Diaries 2 (2004) and Just My Luck (2006). His roles include Cinderella's Prince in Into the Woods (2014); Jack Ryan in Jack Ryan: Shadow Recruit (2014); Bernie Webber in The Finest Hours (2016); and Robert the Bruce in Outlaw King (2018). He starred in Unstoppable (2010), Rise of the Guardians (2012), Hell or High Water (2016), The Contractor, Don't Worry Darling (both 2022), and Dungeons & Dragons: Honor Among Thieves (2023). Pine made his directorial debut with Poolman (2023). In 2025, he acted for the first time in a non-English role (Italian) in the movie The Kidnapping of Arabella, which was also praised at 2025 Venice Film Festival in the Orizzonti category.