Though most of his scene was cut from the movie, Timothy Olyphant (Hiker) later said he was hugely inspired by watching Holly Hunter work and the creative choices she made. He said his experience on his first few roles up to that point had been relatively uninspiring, but seeing how focused Hunter was made him want to keep working. A Life Less Ordinary is, in fact, only Olyphant's second feature film role, the first having been in The First Wives Club (1996).
The scene where Robert (Ewan McGregor) almost hits O'Reilly (Holly Hunter), who is lying in the road, was shot backwards and then reversed in post-production.
Although Brad Pitt met with Director Danny Boyle and Producer Andrew Macdonald, the lead part was written with Ewan McGregor specifically in mind.
Ewan McGregor looking under the floorboards for the money is a nod to Shallow Grave, which was also about stolen money. It was Boyle and McGregor's first film together.