- Apparently, his first job on a film shoot was working as Lindsay Anderson's assistant in his early twenties, a position he described as "...basically holding cups of tea".
- He is a keen admirer of the New German Cinema, particularly the films of Rainer Werner Fassbinder and Wim Wenders.
- Was approached to direct Good Will Hunting (1997) for $1.5 million but declined.
- His former partner Sabrina Broadbent wrote a novel, "Descent", which "The Manchester Guardian" describes as "closely based on their life together. Or rather, not together, because the husband in the book is understood to be a workaholic film director who keeps disappearing in pursuit of interesting projects". ("A Winterbottom's Tale", February 1, 2004)
- Has made three movies based on novels by Thomas Hardy: Jude (1996), based on "Jude the Obscure," The Claim (2000), re-setting "The Mayor of Casterbridge" from rustic England to a California mining town, and Trishna (2011), an update of "Tess of the d'Urbervilles.".
- Member of the 'Official Competition' jury at the 51st Cannes International Film Festival in 1998.
- Co-founder of Revolution films (UK); along with producing partner Andrew Eaton.
- Often works from a script by Frank Cottrell Boyce.
- Often works with cinematographers Marcel Zyskind (In This World (2002), Code 46 (2003), 9 Songs (2004)) and Alwin H. Küchler (The Claim (2000), Heartlands (2002), Code 46 (2003)).
- Went to college with director Marc Evans (Resurrection Man (1998), My Little Eye (2002), Trauma (2004)). Winterbottom's company Revolution Films produced Marc Evans' second film Resurrection Man (1998).
- Was the original director chosen for The Cider House Rules (1999), Goal! The Dream Begins (2005), and Freedomland (2006) and did extensive work before leaving each of those projects.
- Attended Oxford before going to Bristol University to study film.
- Was approached to direct The Cider House Rules (1999).
- Often flies economy with his crew.
- Hoped to use the sets of Danny Boyle's film Sunshine (2007) on the production's off-days to shoot his own science fiction comedy. Permission was never worked out and Winterbottom's film was canceled.
- Has two daughters with Sabrina Broadbent.
- Went to Queen Elizabeth's Grammar School in Blackburn.
- He visited Argentina for to promote his film Tristram Shandy (2005) in Mar del Plata International Film Festival. (March 2006)
- Many of his films are 'road movies' or at least include road trips or voyages to other countries as part of their stories.
- He was replaced by Danny Cannon on Goal! The Dream Begins (2005) after the producers saw some of Winterbottom's early footage and found he was making it more like a documentary drama rather than a straight drama as they wanted.
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