My hair tends to have a mind of its own and it loves to stand up. Every time I have it cut I always hear the "boy, your hair just loves to stick straight up!" schtick from the stylists (gee, that never gets old). I have a rough time getting it to do anything until it gets longer and by then I'm tired of it and ready to cut/the cycle repeats. It's also normally very straight, which gets annoying (I know people with curly hair will probably want to kill me for complaining about straight hair ;P).

Here's a pic of a few ways my hair has gone in the last few years: http://imgur.com/tQ96O - http://imgur.com/tQ96O Usually it's just some variation of those.

And here's what I'd like to do (sans bleaching): http://imgur.com/a/EkWgN - http://imgur.com/a/EkWgN

I have absolutely no idea how to go about making this happen. How long/short should my hair be for this? Is this even possible for someone with straight hair? (It looks like his hair is somewhat curly). What products? What methods? I am truly lost at this sort of stuff, so some (major) hand-holding might be necessary here.  Pics or video would be even better (I definitely learn better via visual) but I don't want anyone to go out of his/her way for that.

Thanks in advance for any kind of help..