It's hard to imagine an uglier piece of metal and wood than some of the contraptions churned out by H&R. As far as ugly ducklings go, H&R handguns might take the cake.
Harrington & Richardson has been out of the handgun business since the company (then doing business as H&R 1871, Inc.) was acquired by Marlin in 2000. Most people probably didn't even notice.
H&R handguns weren't ever anything you'd brag about owning, unless maybe it was one of their USRA single-shot .22 target pistols or maybe a nine-shot top-break Model 999 Sportsman. I've owned one of the former and two of the latter, and I never felt ashamed of them. I must admit, however, that most of H&R's pistols and revolvers look positively clunky and stupid compared to, say, a Colt Police Positive or a S&W M39.
But for pure butt-ugliness, nothing could approach H&R's .32 Self-Loading Pistol and its Model 925 .38 S&W revolver. Hoo boy! The .32 Self-Loader was a licensed knockoff of the British Webley7.65mm Pocket Auto (and was also available in a scaled-down .25 ACP version), but the Model 925 sprang unassisted from H&R's fevered corporate brow. Neither was a cheaply-made gun; it's just that their styling was so impossibly awkward that they look weird even to my jaded eyes, which is saying quite a lot.
I've tried to include as much information as possible about these guns in the 2011 Standard Catalog of Firearms (21st Edition), but I haven't quite been able to give them the coverage they probably deserve. However, when you consider that the book contains info on more than 25,000 different firearms from around the world, it's a pretty good one-volume reference/value guide for the firearms generalist who buys and trades guns fairly regularly — as I do.
Anyway, these two poor, forlorn H&Rs are my candidates for Ugliest Pistol of All Time. In my experience, both were utterly reliable and acceptably accurate, but let's face it: they're about as pretty as the southbound end of a northbound mule.