The prize for the worst car I have owned would have to go to the 1981 VW Vanagon.... loved it but It could always be counted on to fail somewhere enroute to wherever we were going.

The prize for the best car I have owned: 1996 Jeep Cherokee, 245,000 miles and still looks and runs about as good as the day I brought it home.

Some others I have owned over the years, in no particular order:
1952 Ford 2 door
1950 Chevy 2 door coupe
1950 Austin A50
1962 Impala 2 door HT
1949 MG TC
1957 Chevy Bel Air 2 door hardtop
1955 Chevy 2 door Bel Air sedan
1967 Shelby GT 350 (still dream about it sometimes)
1969 Lincoln Continental
1969 Chevy Chevelle Concours
1972 AMC Gremlin (couldn't be killed)
1979 VW Van
1991 Ford Aerostar Van
1979 Toyota Landcrusier
1981 Toyota Landcrusier
1993 Toyota PU
1994 Toyota Tundra PU
2004 Jeep Rubicon
2004 Jeep Grand Cherokee** (still own)
2003 Jeep Liberty
1996 Lincoln Continental
1958 Chevy Apache PU
1964 Chevy 1/2 ton PU
1972 Chevy 1/2 ton PU
2006 Yellow Crossfire Roadster (I'm in love again after all these years)