Outdoors in the dark, when you aren't competing with the sun, the range is good. But there are still usually nothing to bounce from outdoors, so line of sight apply.
Having a master like the 580 EX II as a master allows you to aim it towards the slave, if that's something your artistic intentions also allow.
Here's a picture taken outdoors with a 580 EX II as a master on the 7D, and another 580 EX II on the other side of the path.

