No, this is unfortunately not possible.
The closest thing would be a smart playlist similar to this:
(but without the ordering by air date)
which you then play in Shuffle mode.
But in the end it still will go through every episode. And when every episode has been played, you need to reset those shows to ‘unwatched state’.
A simpler approach would be to put your favorite shows into a collection.
Then you create a custom filter in your tv show library and set
‘Show Collection’ is ‘my favorites’
Then click on ‘Add to Playlist’
However, with this approach, it is not tracked which episodes have been played and thus duplicates can occur when the playlist is resumed.
