Randomizing a TV show folder for playing

I couldn't figure out how to describe this in the title. Maybe someone can help me out.

As I've posted before, I'm seriously considering switching from Mediabrowser and I'm trying to get like for like functionality while getting all the cool stuff XBMC has on top.

One of the features I use with my kids is the ability to click play on a cover art for TV they watch, inspector gadget for example. Once I click on it it asks to "Play All", which starts at episode 1 and plays through or "Shuffle" which randomly picks shows over and over till we've gone through every episode (which is about 100).

I like this because I can just click on random and leave them be without them asking me to start another show.

Is there anything similar to this?

Thanks for the help

Josh