As per my grandfather, a man who truly loved guns and was fascinated with guns (he had 19 up until WWII, his sister sold all but four, and of those four he kept three while trading one as part of a deal for a used 1950 Ford Fordor) the greatest .22 caliber semiautomatic pistol ever made was the Colt Woodsman. However, whilst he didn't own a .22 revolver, he was of the opinion that of the guns he'd fired, the best was a Smith & Wesson K-Frame .22. If you're going to ask me what kind of K-Frame .22, my uncle was trying to figure that out for years and eventually gave up. My grandfather had access to this gun for just one year, though: 1953. Its owner moved away after that. My grandfather got his first gun in I believe 1920 and his last in 1940.