The oldest one is my fathers 700 that he gave me when I was 14 and he got when he first started hunting, it was bought used in the mid 60's, I actually don't own it anymore since I gave it to my son since..
I tend to not fall in love with hunting rifles and I have many, most are newer and not very old since I am always changing stuff up, I have an a400 unico for turkey, I have a Browning Silver rifled 12ga for deer {shotgun season}, Rem 700 mountain in 7-08 for deer rifle, Beretta 686 o/u for bird, and the OLDEST of my rifles that I actually hunt with is probably my Ruger 77 in 22-250, its setup for yotes and I just cant talk myself into replacing it I thought about it since I own some really nice coopers, I think I used that to kill more animals than any other gun I have ever owned...
Then I have an array of small varmint guns, all cooper bolts and one Blazer {also have a beautiful ar 204 wilson combat custom but do to recent law changes its not kept at my residence any longer}, and a choice of a few other bolt guns for longer range and bigger game, just depends on the hunt and what I pack up the day I'm leaving, 300wsm, 338 lapua, 308 win.
I used to get atttached to huting rifles, but then I got into bow hunting, and from swapping bows every few years it got me used to it so if a new style rifle comes up that I want to try, I do, if its better than what I am using, I will sell the old one to make room for keeping the new one, if not, Ill sell the new one...