My "funnest" 22's have never needed expensive or fancy. I have several vintage Remington rifles that are tack drivers, and easily the most fun is a Nylon66. There's also the Marlin Model 60 which I way prefer to the 10/22 due to the tube magazines (Ruger rotary mags always fail at the wrong time for me). For pistols, I like SAA-style but it's hard to argue with a Ruger SR-22 or a Walther P-22 for sheer fun.