73 VW Super Beetle (first car at sixteen)
71 Chevy Malibu (bought as driver when VW became a show car, later sold outright)
86 Chevy Cavalier Z-24
90 Mazda MX-6 (replaced the Z-24)

Then got married so adding wife's cars since we owned them jointly:

91 Honda Prelude Si
94 Honda Passport EX (replaced the MX-6 when baby came)
92 Jaguar XJS V-12 Convertible (replaced the Prelude)

Then came the MBs...

99 ML320 (replaced the Passport)
93 300E (purchased outright)
95 SL500 (replaced the Jaguar)

And the fleet stands as is for nearly four years...

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2009 ML350 (106K) - Family vehicle
2001 CLK430 Cabriolet (80K) - Wife's car
2005 BMW 645CI (138K) - My daily driver
2016 Mustang (32K) - Daughter's car