I tried out a whitewater boat the other day. If you are having trouble getting your first roll I recommend trying a whitewater boat. They are so easy to roll it feels like cheating. Now that I think about it I should try some of the more difficult traditional rolls in it, like the elbow roll and the elusive kingup apummaatigut (behind the back roll).
I’m an awful rolling instructor by the way. I let my students struggle underwater a long time before rescuing them. They come up sputtering, their lips a blue-gray color. Then I just yell, "You need more hip snap!"
One piece of advice when you are doing an Eskimo bow rescue: if you are being rescued please check on both sides for the bow of your rescuer -- underwater you lose all sense of left and right. In fact, when it comes to rolling don’t even bother talking to me about left or right, and especially (as my friend Ricardo likes to do) port and starboard! Those terms become pretty meaningless.
Then there is that interesting piece of advice from Greg Stamer about the behind the back roll: it’s easier to learn if you start from the finish position and work backwards. I’m still trying to figure out what the hell that's supposed to mean! Here is a little movie related to that, pieced together from random clips taken by Dick and me. Enjoy!