On the light side. A High Point C-9, 9mm. I got it years ago, after reading about how bad they were. Especially on this forum, there was one guy who had made it his life's mission to destroy High-Point for one reason or another. He had never seen a good one, despite having handled and even owned apparently, dozens of them.
So I got one, and that goofy thing just chugged along all day long, no matter what ammo I fed it, hitting what I shot at with it. I kept it several years, shot the snot out of it, then sold it for what I had paid for it.
On a more serious, but still "fun" side, my recently purchased Cimmaron/Uberti reproduction 1871/72 Open Top Colt, 44 Specials. Two of them. I was surprised how easy it was to shoot them accurately, or at least as accurately as I shoot any handgun. The rear sights are downright tiny, and I've actually found I'm really just sighting down the barrel at the target. They seem to point like a natural extension of my arm. Those old timers seemed to have known what they were doing. I'm not a S/A guy, but these are top notch. And they look great too.
Modern. Or as modern as I get. The used Ruger P95DC I picked up for a "range toy." It's big, it's ugly, it's bulky, but man does it shoot. I make no claims of being a good pistol shot, but that gun makes me look like I know what I'm doing. My wife too. I can almost see the bullet going right where we have it aimed. It's not that I expected it to be "bad", after all Ruger has a pretty good reputation for making guns, but I was really impressed. And I'm an old revolver guy so that's high praise from me. Oh, and the only "malfunction" was with a bad magazine I had to weed out. The other magazines I've got for it have been perfect. It also has a very "soft" recoil compared to other 9mm's I've fired.