Funny, we were just having this issue with our kids videos. Possibly you can utilize the example of Suggestions on Netflix or iTunes to drive the Decision based on current or recent activity or maybe decide for me based on genre. I mean if you were in a bad mood, you may prefer comedy over a random romance.
I wrote a script at one time that was a decision tree for building a custom playlist based on genre and other selections. That way when it referenced my play counts and recents, I wouldnt end up with recent music my wife was listening to… Celine Dion…yuck. Sadly I didn’t build it right because her recents kept making their way in… But I am sure someone else has the smarts to do it.