Fun and Gains: old on the tail female line. Oldest current pedigrees for total age?

I'm not sure if I've betrayed this weakness on the blog yet, but having somehow gotten it into my head that the age of a horse's dams was interesting, I always notice them when I retrieve pedigrees. It's not an obsession, but a very small part of my brain is needed to notice the dams' ages, I guess, and and if something is of interest there, the small part of my brain assigned to the task will alert the rest. There was an alert today for Fun and Gains, a 3-year-old filly 3rd in the 9th at Keeneland in her debut. Her dam, Richwood Girl, is just a 1999 model, but she becomes more of an anomaly as you keep going back. The 2nd dam was born in 1979, the 3rd dam in 1960, the 4th in 1943, and the 5th in 1927. The degree of datedness of the 4th and 5th strike me as the real standard bearers. I think it will take a lot of looking to find a 2009 horse with a 5th dam that dates to before 1927. Granted, the tail female line really just tells you about one quarter of the pedigree, but I like thinking that we are actually regularly seeing matchups of horses from different eras, genetically speaking.

I suppose my antennae should expand to note total datedness of a pedigree. You could start with which sires and broodmare sires have the most dated pedigrees; they repeat, after all. Then you could sort of have a dream cross for the oldest pedigree, genetically speaking, and hope that somehow the tail female line resembled Fun and Gains's. People could even breed with this aim in mind. It would be wacky, and reckless if money were involved (which it always is), but it wouldn't surpass some other approaches I've heard. And it would provide me great amusement.