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They do look cool when your following him on the road......
There are, I'm sure, many ways to attach them. There are good write-ups on 2 different ways here:
http://www.vulcandrifterriders.com/forum/index.php?topic=42821.msg95255#msg95255 http://www.vulcandrifterriders.com/forum/index.php?topic=42821.msg95255#msg95255drifterriders.com/forum/index.php?topic=42794.0
The 59 caddy lights fit pretty well directly on the stock Drifter tail light. The "cup" or "backing" for the caddy lens can be adapted easily to screw to the stock kaw housing. Then it's a simple matter to attach the caddy lens to the backing. The caddy light is then kind of heavy for the rubber-mounted kaw light housing, sometimes causing the light to sag a bit. Some folks, including me, made some type of bracket to help support the light.
I used this method on my first attempt, but later I adapted HD turn signals with rigid mounts to the Drifter bumper. The caddy lights are slightly smaller in diameter than the HD light housing - so I made an aluminum adapter to bolt it on. I was pleased with how they turned out - I also have HD markers on the front, so they match.
Well I was browsing through eBay for Cadillac lenses and some of them do call out a diameter. Some which cost a little more do include the mounts. it seems to me you're going to need some type of adapter made, probably out of aluminum. that's what machinists are good for 
dumb question here, but what's the way to know these would even be close to fitting on a drifter?
they don't call out a diameter do they? I think they look really cool, seen them on old vintage indians, but the ebay site fitment charts all show actual Cadillacs--my year 1959
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You might want to reach out and pm GreenBarn and Rockin ronny because I know they both did this mod......
Wondering for those of you out there that have the 59' Cadillac lenses if there is anything special about putting them on the back turns? Looking at the ones below can't visualize how they would connect/stay on. What am I missing? Is there another part needed? Pics if possible? Looked at quite a few on ebay and they all look like there just the lens.
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