My first was the Canon A-1, which I bought used with the nifty fifty for probably $100 in the early nineties, when I was in junior high school. Eventually I added 28 and 135 mm primes via ebay. I used this into college, even in a B&W photography 101 class for art majors. I still have my darkroom supplies, and I even purchased an enlarger, timer, and easel -- none of which have been set up or used in at least 17 years.
I made the jump to digital in 2004 with a cheap canon P&S A-series something or other, purchased mostly to take easily-deleted blurry pictures of our first puppy. My wife bought me an Elph SD800IS as a wedding present in 2007.
Missing my old SLR days, I got the Rebel t1i in 2009 or 2010. I added the 20mm and 100mm macro when we decided to travel to Madagascar, although I should have practiced a lot more before we left!
I bought the G1x when my son was born in 2012, so I would have something that took quality photos at the hospital without taking up too much space. Once he started crawling and got mobile, I decided a full-frame camera would allow me to make better use of my 20mm prime as he spent most of his time crawling directly at me. I added two film cameras (Rebel G and then Elan 7n) before I decided to just go with a refurbished 6D. Once I get caught up on downloading, sorting, and backing up the digitals, I'll think about getting the darkroom set up again...