I believe of my lenses, I have 4 that are tied for the same age.
All SMC Pentax K mounts. This includes 50mm F1.4, 105mm F2.8, 135mm F2.5 and 300mm F4.
see the attached link for the 300 F4, it has been referenced by me many times on the forum
https://www.pentaxforums.com/forums/106132-post4.html
there have been ton's of posts by others for the 50mm and 135. Not sure anyone has posted anything yet with the 105mm F2.8. If not I will make this my project lens for the weekend
but note these are definitely not the oldest lenses out there.