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Grant made his feature film acting debut in Privileged (1982), followed by the romantic drama Maurice (1987), for which he gained acclaim and won the Volpi Cup for Best Actor. He then acted in a string of successful period dramas such as The Remains of the Day (1993), Sense and Sensibility (1995) and Restoration (1995). Grant emerged as a star with Richard Curtis's romantic comedy Four Weddings and a Funeral (1994), for which he won the Golden Globe and BAFTA Award for Best Actor. He starred in further romantic comedies such as Notting Hill (1999), Bridget Jones's Diary (2001) and its 2004 and 2025 sequels, About a Boy (2002), Two Weeks Notice (2002), Love Actually (2003) and Music and Lyrics (2007).

Grant began taking on against-type parts, earning three BAFTA Award nominations for his roles as St. Clair Bayfield in the biopic comedy Florence Foster Jenkins (2016), a haughty actor in the family film Paddington 2 (2017), and a charming yet sinister man in the horror film Heretic (2024). He has also acted in the science fiction epic Cloud Atlas (2012), the crime comedy The Gentlemen (2019), the fantasy comedy Dungeons & Dragons: Honor Among Thieves (2023), and the musical fantasy Wonka (2023). He earned two Primetime Emmy Award nominations for his roles as Jeremy Thorpe in the BBC miniseries A Very English Scandal (2018) and a man accused of murder in the HBO miniseries The Undoing (2020).

Grant has been outspoken about his antipathy toward acting, his disdain for celebrity culture, and his hostility toward the media. He emerged as a prominent critic of Rupert Murdoch's News Corporation during the News International phone hacking scandal.