Not sure how "Cool" it is since there's an entire thread on rebuilding them, but here's my early-vintage Craftsman 100.
It was my wife's Grandpa's. Gotta be about 75 years old, but I don't know exact year. He moved to California in 1942 and likely picked it up a few years after that. Her dad kept it in the garage after his passing, but never really used it. I put it to work a few times - which is when I noticed it needed a belt and some hardware, and could use a good going-through.
I tore it down (initially just to move it from house to house, to house), installed a larger (specified 1/3HP) motor; replaced motor, pulley and quill bearings, standard hardware, and belt. Removed decades of gunk from the quill, pinion, head, and chuck. Cleaned up the paint; removed surface rust from the unfinished column, rods, and chuck.
Without help from FrankLee and a bunch of others on the Craftsman Drill Press site, I would have left in on the curb and picked up a cheapie little benchtop unit. But this is way cooler than that, and a good bit more useful, too.