I read somewhere that in ChatRoulette.com it is possible to replace the webcam with a video or a picture and it seems that some people do it. How? Does anybody know? Thanks.
I recommend e2esoft VCam (http://www.e2esoft.cn/vcam/)
Since it emulates a webcam it works with (almost) every piece of software or web application out there.
It allows you to stream pretty much everything ~ images, video files, flash movies, applications, your desktop ~ along with the footage of your real webcam. Another nice feature is to add an overlay to the stream e.g. pictures, other videos, text, or even paint on it.
It's a 30-day trial with a watermark or ~30$ for the full software.
Nice app but a bit pricey in my opinion.
Chatter, this free software should do the trick and more besides: