Originally posted by CWyatt One really big point I haven't seen mentioned (might have missed it) is focusing distance. This has a major effect on depth of field with any speed or focal length lens.
Bingo! The distance between you and your subject compared to the distance between your subject and the background will have a greater effect on OOF than a lens that's 1 stop or even 2 stops faster than what you've got.
If you are doing soccer, for example, if you are low to the ground and you've got 20 meters between you and the action and an additional 100 meters between the action and the trees in the background, the trees will probably be OOF whether you use F2.8 or F4.0. And with sports, you'll probably want F4.0 at least to increase the chances that your moving subject is in focus.
Likewise for the street. Try it with your kit lens at F4.0 - you 3 meters from your subject and the background 10 meters or more away. The background will be OOF.
Here's an example of the kit lens producing OOF with F5.0:
Ok, now for a stupid pun..."There she was, bokeh walking down the street, singing doo wah diddy diddy dum diddy doo."