Hmmm...
Could not get smart playlist to work. It found all the files and made a list but, no option to Watch All.
I ended up copying the files I wanted in my playlist list (532) to another folder and then re-tagged them with a common series name to group them all together. (I have a lot of storage available so could afford to do so). I also changed the Season tag to 1 so it would flatten the view.
Now, when I go to TV>Series I can see my new folder and clicking on it brings up a list of all my assigned files. I can now click Shuffle All and away we go. A workaround but it does what I wanted.
For what its worth:
I also tried to add it to the main menu and assigned the Rule "Series is Comedy Central" (what I called it) but when the list comes up, there is no option to watch all. So, I went with above workaround.