The Super Cub
Otherwise a fairly conventional tailwheel ... however, I think the fellow who coined the phrase "the most fun you can have with your clothes on" certainly was talking about SuperCubs ...
Let's dispose of this one first. I'd suggest, from experience, that a night sky dive trumps flying a Super Cub (and yes, I have sky-dived out of a Super Cub but that was in daylight...).
Now, where were we. Oh yes. My first tail wheel flying was in a 135HP ex Dutch military Super Cub - the second was was an hour later in a Terrior (now that's what I call "character building"). Took to it very well in the end. I'd got about 18 hours P1 by then (C152) and 50 hrs dual.
Don't recall it being hard to fly but... what was different was the tail wheel ethos.
Glide approaches (no throttle against brakes as it was explained to me), low flying, gentle opening and closing the throttle, watch out for the wind turning the 'plane on the ground, holding off on landing in the three point attitude....
One thing was explained to me (it worked for two cases). Watch where things are pointing as that tells you which foot to press on the rudder.
1) The turn and bank has a pointer which points to the foot you press on the rudder to keep it in balance
2) Whichever side of the nose the propeller goes tells you which foot to press when taking off.
Other than that, Super Cubs are great fun. Haven't flown one for years now (did fly one of floats) - got sidetracked by skids rather than tail wheels and then moved onto a Cub which is only a cycle ride away.