There's a book out based on your grandfather's "When I was your age" adage by Portland illustrator Dennis Adler. Wax Lips and White Bucks is a graphic novel full of vignettes that look "back at what we did in the 40's and 50's." Adler's cartoons explain how he and his friends used to get their kicks by flattening pennies with the force of a moving train and floating in previously abandoned truck wheels at the public swilling pool.
Though Adler's perspective is a bit dusty—he explains the acts of giving and hiding a hickey as a thing of the past—and is a little heavy on the family values—"Mom was always home…Moms and Dads stayed married"—it does shed light on some cultural nuances that baby boomers failed to pass down to their X and Y Gen progeny. I now know that a pneumatic tube is a pressurized pipe used to fly paper between desks in an office.