Seamlessly Play Multiple Videos

Here is my dilema. I will have a group of 20 items and the user will be able to select up to three of them. After clicking a compare button, it would load a video for each item and play them back one right after another, seamlessly with no transition.

It’s my desire to use javascript instead of flash for this. I’m learning the ins and outs of JQuery right now. Is this possible using JQuery? Am I on the right track?

Any advice on what direction to take would be appreciated. Thanks in advance!