Springfield xd 9mm-still have it, 5 years now been through hell and back because I used it everyday at work but still running like new =) I'm a springfield fan, I'm in the process of building a socom II =D
Colt 1911 Gold Cup model from the late 60's. I bought it off my wife's uncle's estate last year for what I found out was a very cheap price. Word of advice, if someone in your family passes away, find someone you can trust to estimate the value of the guns. I'm just glad it stayed in the family for the price I paid for it.
My first handgun was a TC Contender with a 10" 44 mag barrel. I got it for my 16th birthday in 1991 from my father, I still have but don't shoot it as much anymore but when I do, it still puts a smile on my face.