Young people have frequently used automobiles as an essential part of their urban experiences in many, if indeed not all countries worldwide. In the second half of the twentieth century in particular, youth's exploitation of the car as a place of desire and adventure – providing them with a mobility across cities, bodies and identities – has also been one of the central fascinations of film, thus representing and promoting this engagement to mass audiences worldwide. This essay therefore looks across a range of movies in which young people are depicted as directly experiencing automobile driving, and then turns to examine one pair of films in particular – the two versions of The Italian Job (Peter Collinson, 1969, and F. Gary Gray, 2003) – in order to show how urban driving in general has become associated with youthful attitudes to urban space as a place of desire, danger and play.