This topic is something I kinda live in real 1-1. I have always looked at cars from a tool perspective. Thus, I already have a goofly portion of the five I'd need to make this list. They are, in no particular order:
Dodge Ram 2500 pick up. I've got to have some thing for around the home / yard projects that require the moving of large and or dirty items.
Dodge Grand Caravan. Perfect for family vacations.
Porsche 944. Got to have a sports car! This one is one of the best handling cars ever made, looks great, is built like a tank, and gives good mileage when traveling the interstate.
Now for the ones I don't have to complete the list of five.
Volkswagen R32. The perfect golf. All wheel drive and an amazing V6. Perfect for the Dan Ryan in Chicago in any weather!!
Last but certainly not least..... the wife should have a daily driver that is fun. For her, my choice is a Mini Cooper S.
Yeah, I could live with these for the rest of my life.