[citation needed] Greengrass moved into drama, directing non-fiction, made-for-television films such as The One That Got Away, based on Chris Ryan's book about the experiences of the British Army's Special Air Service during the Gulf War and The Fix, based on the 1964 British betting scandal.

His 1998 film The Theory of Flight starred Kenneth Branagh and Helena Bonham Carter, who played a woman with motor neurone disease.

Based on the Omagh bombing of 1998, the film was a critical success, winning British Academy Television Award for Best Single Drama.

The film starred Matt Damon as Jason Bourne, an amnesiac who realises he was once a top CIA assassin and is being pursued by his former employers.

An unexpectedly major financial and critical success, it secured Greengrass's reputation and ability to get his smaller, more personal films made.

For his role in writing the film, he earned the Writers Guild of America Award and a BAFTA nominations for Best Original Screenplay.

[10][11] Greengrass's Green Zone stars Matt Damon as the head of a U.S. military team on an unsuccessful hunt for weapons of mass destruction in post-war Iraq.

[12] The film was first announced as based on the bestselling, award-winning, non-fiction book Imperial Life in the Emerald City, by Rajiv Chandrasekaran, the Washington Post's Baghdad bureau chief.

But the final film is a largely fictionalised action thriller only loosely inspired by events in the book.

[15] In February 2019, Greengrass signed on to direct the film adaptation of the Paulette Jiles novel News of the World for Fox 2000 Pictures, reuniting him with actor Tom Hanks.

[17] In May 2022, it was announced that Greengrass would write and direct medieval action film The Hood, starring Benedict Cumberbatch and based on the story of the English Peasants' Revolt in 1381.

[19] In November 2023, it was announced that Greengrass would write and direct a film adaptation of the T. J. Newman novel Drowning: The Rescue of Flight 1421 for Warner Bros.

[20] In January 2024, it was announced Greengrass would direct the thriller The Lost Bus, written by Brad Ingelsby and based on the 2021 nonfiction book Paradise: One Town’s Struggle to Survive an American Wildfire by Lizzie Johnson, about the 2018 California wildfires, for Apple Studios; Matthew McConaughey and America Ferrera will star in the project.