I can well remember seeing my grandfather toss his toolbox into the back of his pickup on his way to the construction site he worked at. Not secured to anything, it slid all around the pickup bed, denting up the bed walls and probably the tool box. He fussed when it turned over, which meant the tools inside rolled around where they weren't supposed to. I remember admiring his ingenuity at wedging the tool box behind some lumber that fit crossways across the bed, in front of the wheel wells. Seems like a paint bucket or maybe his spare tire further secured it. He was such a genius in my mind!
But that's what folks with tool boxes had to deal with back in the 50's and 60's. How excited he was when they came out with the much larger tool boxes that actually mounted to the bed. A double win for him, as it eliminated the rolling tool box, AND it gave him lots more room for tools. Which I'm sure meant he bought some more - not hard for him.
While his truck tool storage box days ended with his carpentry jobs, his new gig as a senior apartment complex manager moved all of his tools inside. He and my grandmother managed a building in Palo Alto, California which had formerly been a downtown hotel. A fairly old building, it had a garage and a huge workshop underground. His tool collection in that workshop looked like something out of "This Old House". He virtually had a tool for everything. And every tool had its place. A giant tool box of sorts!
I remember when they retired ( at age 80 ) and moved to Northern California, his workshop went along, moving now into an out building behind their house. It was the size of a two car garage and what a set up. He continued to garage and yard sale shop for more tools forever. Funny, though, I can't remember him ever selling any at one!
When he was 86, he had to have open heart surgery. Only time I ever remember seeing him scared. After the surgery, he pretty much gave up on life, and had been in a nursing home rehab place. He refused the therapy and got pretty sad and stubborn. I was out there on a trip and went with my grandmother to see him. Seeing me perked him up some, like maybe he didn't want to damage his reputation with me. And at some point while I was there, my grandmother seized upon the moment, and suggested to him that since he was never coming home again, she was getting ready to have a big garage sale to sell all of his tools! She was such a wise woman!
Needless to say, my grandfather started therapy the next day and was released a couple weeks later. It was like, "you can do what you want to me, but I'll be danged if you're gonna touch my tools!" Sadly, when he died a few years later, his tools all did get sold before my brother or I could get there, which saddens me to this day. I'm not a greedy guy, but those tools always meant something to me, and would've because they were his. Too bad.
Anyway, if you're looking to upgrade your own truck tool storage box, there are a number of great sites out there with lots of different styles and configurations. While I can't imagine my grandfather on-line or on a computer, he would've sure loved these new tool boxes.