I'll "cheat" a little - drill press, screwdriver set, socket set, pouch of wrenches and a hammer. If I'm living out of the car or something, I'll trade the drill press for a set of pilers. With some duct tape and some bailing wire cut off a fence with the pilers you can just about fix anything.
If you mean 5 individual tools: Medium size ball peen hammer, Leatherman tool, 4 way screwdriver, 12" Cresent wrench and a medium size pair of pliers. You gotta have a hammer - if you can't fix it with the other stuff, you can always beat to the point where NO ONE can fix the [email protected]
Sentimental? I have a bunch. I have a pair of red handled needle nose pliers that belonged to my dad - it was in the small garage tool box. He was an electronics guy (IBM), so most of his stuff whas small, except for some sockets and wrenches for working on the mower. Most got stolen after he died. I still have a couple of the old wrenches. Funny - dad's hobby was electronics and his tool box was about 18" tall. I'm into cars and my rollaway with the track tool box sitting on top is about 7 1/2' tall.
I cleaned out an old tool box that belonged to my grandad and found what looks like an old, rusted Model A wrench with the FORD script still on it. It's in the box with the Craftsman's.
When I was almost 13 and my mom and dad were both gone, my Grandmother asked me what I wanted for my birthday. I picked a 1/2" and 3/8" Craftsman socket set from the Sears catalog with a 1/2" S&K wrench and 3/8 Craftsman wrench. The 3/8 socket wrench has been long replaced, but the rest is still my primary set. Those sockets are in my hands doing something for me at least once every week. I hope that my grandma -rest her soul- knows it.