I'll base this on most fun to drive because these were not always best vehicles.
#1 Gawd-Awful Pontiacs--'74 Bonneville, '71 Catalina, '76 Grand Prix--huge, powerful, road-holding cars. Great handling for their size and loved the roar of the Q-Jet with the lid flipped over. These cars were really good. Like my old M16A2 service rifle, I close my eyes and I can feel the wheel and see the dash of my old Bonneville.
#2--VW bus--like driving a 1/8th scale semi; all the gears feel the same as you work your way up. Huge gearing like a tractor, decent mileage, easy to do the required 40,000 mile overhaul. Lots of interior room. Love the clean simple design.
#3--AMG Hummer. My first offroad vehicle, small size one anyway, I drove 5-tons first. I spent a lot of time messing around in these. The huge width, 37" tires, 18" ground clearance, triple Torsens and diesel engines--these are like a video game offroad. Just point it and it grumbles over anything. It will go straight up a hill that you will need to pull out the throttle lock and squat in the seat to see. They might tip over on the RTI ramp, but in practice, they are hugely impressive.
#4--Our old Honda CR-V. Little packet of an SUV. Decent mileage. SImple self contained 4wd system that needed no maintenance or driver input. Great power though without the V-Tec crap it used lots of revs to get it. The interior was sooo solid--like the car was carved from a solid piece of plastic. I really hated when we out grew that thing and had to move up to the Pilot.
#5--Mazda B2600i pickup. Like driving a good handling campact car, but with a 6' pickup bed. Held 1,000# of gravel and still drove nice. Very stout 2.6L 4-cylinder engine. The whole vehicle was seamless in design and construction. Pulled our 16' travel trailer all over--bulletproof automatic trans. If it were a 4X4 I would never have gotten a Ranger and been a part of TRS.