Civil War Vet with Jet article
Civil War Veteran Bill Lundy interacts with some Airmen and a jet fighter.
There is some debate on whether he was actually in the war. Regardless there in, it illustrates how it was possible for a man to fight in the American Civil War with a muzzle loader, and see jet fighters in his later years. It's amazing how few generates seperate us from the Civil War and even the Revolution.
General "Light Horse Harry" Lee of the American Revolution was the father of the famed General Robert E. Lee of the American Civil War.
Civil War General Simon Buckner was the father of General Simon Buckner Jr. who was killed during the Battle Okinawa in WW2.
EDIT:
I know a MSG who's father fought in WW2. He's deployed to Iraq and Afghanistan.
So potentially 3 generations could span all of U.S. history.