[1] He and co-director Mat Whitecross won the Silver Bear for Best Director at the 56th Berlin International Film Festival for their work on The Road to Guantanamo.

[13] Butterfly Kiss, Winterbottom's 1995 debut feature, followed a mentally unbalanced lesbian serial killer and her submissive lover/accomplice as they fall in love while slaughtering their way across the motorways of Northern England.

[7] That same year, he reunited with Jimmy McGovern for the BBC television film Go Now, the story of a young man who falls ill with multiple sclerosis just as he meets the love of his life.

It was an adaptation of Winterbottom's his favourite novel, Thomas Hardy's bleak classic Jude the Obscure, a tale of forbidden love between two cousins.

It was based on the true story of British reporter, Michael Nicholson, who spirited a young orphan girl out of the war zone to safety in Britain.

Starring Rachel Weisz and Alessandro Nivola, it was inspired by the Elvis Costello song of the same name and shot by Polish cinematographer Sławomir Idziak,[16] who won an Honourable Mention award at the 48th Berlin International Film Festival for his work.

[17] He followed that with 1999's With or Without You, a Belfast-set comedy starring Christopher Eccleston, about a couple trying desperately to conceive, who each have past loves re-enter their lives.

[19] Starring Gina McKee, Shirley Henderson, Molly Parker, John Simm, Ian Hart and Stuart Townsend, it is the story of three sisters and their extended family over Guy Fawkes Day weekend in London.

[22] Many of the production difficulties, including unsuccessful attempts to cast Madonna, were explained to the public on the film's unusually frank official website.

[14] 24 Hour Party People, released in 2001, documents the anarchic, drug and sex-fueled rise and fall of Factory Records and the music scene in Manchester from the late 1970s to the mid-1990s.

[23] His 2002 film In This World depicts the journey of two Afghan refugees from Pakistan, across the Middle East and Europe to Britain, which they try to enter with the help of people smugglers.

Shot on digital video at a cost of $2 million,[24] it featured non-professional actors and brought Winterbottom numerous awards, including a Golden Bear and a BAFTA for best film not in the English language.

The film marked the end of Winterbottom's lengthy collaboration with Frank Cottrell Boyce,[30] who chose to be credited under the pseudonym Martin Hardy.

Produced by Jolie's then-partner Brad Pitt, it was shot in the autumn of 2006 in India, Pakistan and France and premiered out of competition at the 2007 Cannes Film Festival on 21 May 2007.

It was a family drama about an Englishman, played by Colin Firth, who moves his two American daughters to Italy following the death of his wife.

[34] In 2009, Winterbottom was reunited with his The Road to Guantanamo co-director Mat Whitecross on a documentary based on Naomi Klein's bestselling book The Shock Doctrine.

The film follows the use of upheavals and disasters by various governments as a cover for the implementation of free market economic policies that benefit only an elite few.

"[41] This improvised six-episode 2010 comedy series The Trip, filmed in the English Lake District and written and directed by Winterbottom, starred Steve Coogan and Rob Brydon as the same semi-fictionalized versions of themselves they played in A Cock and Bull Story.

[42] Coogan, an actor unhappy with his career, agrees to write a series of restaurant reviews for The Observer in order to impress his girlfriend Misha (Margo Stilley).

[49] 2012's Everyday, known during its lengthy production first as Seven Days and then as Here and There, stars John Simm as a man imprisoned for drug-smuggling and charts his relationship with his wife, played by Shirley Henderson.

[76] 2019's Greed is a comedy satirizing the lives of the ultra-rich, starring Steve Coogan as a fictional retail fashion magnate, Isla Fisher as his wife,[77] and David Mitchell as a journalist hired to write the billionaire's life story.

[78] The film is set at the billionaire's disastrous 60th birthday party on Mykonos,[79] and explores the divide between the character's wealth and the abject poverty of the workers who produce his products.

The other portions were directed by Julia von Heinz (Germany), Fernando León de Aranoa (Spain), Jaco Van Dormael (Belgium), and Michele Placido (Italy).

[93] Kenneth Branagh stars as Johnson, with Ophelia Lovibond as Carrie Symonds and Simon Paisley Day as Dominic Cummings.

[99] Winterbottom's 2023 political thriller Shoshana, previously titled Promised Land,[100] had its world premiere at the 2023 Toronto International Film Festival.

Reuniting him with his Eleven Days in May co-director Mohammed Sawwaf, the fictional film follows a 13-year-old boy and his family struggling to survive the destruction of war.

[109] In December 2023, it was announced that Winterbottom will direct a new adaptation of Ernest Hemingway's classic novel A Farewell to Arms, starring Tom Blyth and Olivia Cooke.

[112] In 2017, it was announced that Winterbottom was developing a 10-part TV series with Annapurna Pictures about the war in Syria, focusing on the involvement of foreign journalists and Non-governmental organizations.

[116] Set to star Jack Black, the film was to follow a man who loses his job and must keep his family afloat by working as a pot dealer.

It is based on his own experience over his career, and includes interviews with 15 other major British directors: Paweł Pawlikowski, Danny Boyle, Joanna Hogg, Asif Kapadia, James Marsh, Andrew Haigh, Carol Morley, Edgar Wright, Steve McQueen, Lynne Ramsay, Stephen Daldry, Ben Wheatley, Peter Strickland, Mike Leigh and Ken Loach.