Hmmmm, well I have owned a s@#% load of cars in my lifetime.  60 maybe???
Most fun- Boxster no contest.  I still can't believe how much fun these are to drive.
Best dog hauler/grocery getter? - Lexus RX330  Build quality is unbelievable and it's a leather couch on wheels.
Best Workhorse-  89 Toyota 4Runner.  We did things with that truck that no one should ever do and it always came through.  Never broke down, never overheated in 260k miles.
Worst car ever- 86 Ford Aerostar.  I had a young family and needed a minivan.  Parts started falling off before we even left the dealers lot.  It stranded us 1/2 dozen times, leaked oil, burned oil, overheated, LCD dash went blank, couldn't tow a canoe.  Limped it into the Toyota dealership after 3 years and they gave me far more than it was worth in trade for the 4Runner.  Somebody probably lost their job that day.