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This ensemble comedy of 11 interwoven stories set in Dublin shows how the breakup of one relationship has repurcussions on the lives of the people around them. One of those people is Lehiff (Colin Farrell), a thief trying to set his life straight by pulling off one last big heist before retiring, while Detective John Lynch (Colm Meaney) is trying to bring Lehiff down. There's also John (Cillian Murphy), who quits his job at a supermarket to join Lehiff in his plot as an effort to win back the love of Deirdre (Kelly MacDonald), who has recently moved in with a married bank manager, Sam (Michael McElhatton), whose bank Lehiff is targeting, and whose wife, Noeleen (Deirdre O'Kane) ends up being a crucial element in the heist.
Bruges, the most well-preserved medieval city in the whole of Belgium, is a welcoming destination for travellers from all over the world. But for hit men Ray and Ken, it could be their final destination; a difficult job has resulted in the pair being ordered right before Christmas by their London boss Harry to go and cool their heels in the storybook Flemish city for a couple of weeks. Very much out of place amidst the gothic architecture, canals, and cobbled streets, the two hit men fill their days living the lives of tourists. Ray, still haunted by the bloodshed in London, hates the place, while Ken, even as he keeps a fatherly eye on Ray’s often profanely funny exploits, finds his mind and soul being expanded by the beauty and serenity of the city. But the longer they stay waiting for Harry’s call, the more surreal their experience becomes, as they find themselves in weird encounters with locals, tourists, violent medieval art, a dwarf American actor shooting a European art film, Dutch prostitutes, and a potential romance for Ray in the form of Chloë, who may have some dark secrets of her own. And when the call from Harry does finally come, Ken and Ray’s vacation becomes a life-and-death struggle of darkly comic proportions and surprisingly emotional consequences.