I thought I'd have the biggest list going, but some of y'all got me beat. In order of ownership (N) Purchased New (U) Purchased Used:

1972 Plymouth Fury (U)
1978 Jeep J10 Pickup 4x4 (U)
1971 Chevy Nova (U)
1973 Chevy Nova SS (U)
1984 Ford F150 (N)
1985 Nissan KingCab Pickup 4x4 (N)
1978 Nissan 280Z (U)
1987 Isuzu P'up (N)
1989 Dodge Raider 4x4 (N)
1991 Nissan Sentra (ex-wife's DD) (N)
1994 Nissan Altima (ex's DD) (N)
1991 Ford F250 Diesel 4x4 (U)
1992 Jeep Wrangler YJ 4x4 (U)
1995 Jeep Grand Cherokee (ex's DD) (N)
1997 Ford F150 4x4 (N)
1998 Dodge Ram 1500 4x4 (N)
1998 Jeep Grand Cherokee 4x4 (ex's DD) (N)
1994 Jeep Wrangler YJ 4x4 (U)
2002 Chevy Z71 4x4 (N)
2002 Jeep Grand Cherokee Sport 4x4 (ex's DD) (N)
2004 Dodge Ram 1500 4x4 (N)
2002 Jeep Grand Cherokee Overland 4x4 (U)

 

1979 Chevrolet Monte Carlo
1984 Dodge 600ES turbo convertible
1985 Chrysler Lebaron turbo convertible
1996 Ford Explorer
2007 Ford Fusion
2006 Dodge Dakota

 

1994 gmc sonoma
1996 chevy silverado
1999 ford expedition (i KNOW I KNOW SHH!!!)
2003 chevrolet tahoe
2005 dodge dakota

 

I've only had 5 since I was 16... so this is over a 20 year period.

1981 F-100 stepside
1998 Ram 1500
1994 Lincoln Mark 8
1998 VW Jetta TDI
2005 Dakota

 

1993 GMC Sierra 1500 2wd (base model)
1989 Chevrolet Suburban 4x4
1995 Chevrolet Silverado 1500 Z71 Ex-cab 4x4
1994 Acura Integra GS-R (still miss this one sometimes, was a fun little 5spd)
1996 Isuzu Trooper 4x4
2005 Dodge Dakota SLT 4x4

Funny enough my family is mainly Dodge and I've always liked Dodge since I was a little kid but my first vehicle was a hand-me-down when my parents' company spare truck finally got too beat up to use for the company anymore (when that truck needed a "fill-up" that meant gas AND oil) and the next two Chevys were just crazy good deals. That said that '95 was a great truck, never had any complaints about it.

 

1972 Chevy Nova (U)
1974 Chevy Vega (U)
1977 Porsche 924 (U)
1984 Chevy Camaro (N)
1987 Ford Bronco II (N)
1993 VW Eurovan MV (N)
1965 Ford Mustang (U)
1989 Jeep Cherokee (U)
1976 VW Beetle (right hand drive) (U)
1993 VW Cabriolet (U)
2000 Jeep Grand Cherokee Laredo (U)
2005 Jeep Grand Cherokee Laredo* (N)
2002 Dodge Dakota SLT (U)
2002 Jeep Wrangler X* (U)
2006 Dodge Dakota SLT* (U)

*Still own

 

Bump... because this is an interesting thread

 

In the order purchased:

1992 Dodge Dakota LE Regular Cab 3.9L V6 2WD Auto
1981 Ford Econoline E150 Bivouac Conversion 5.8L 351W V8
1990 Chrysler Lebaron GT 3.0L V6 FWD Auto
1995 Dodge Dakota SLT Ext. Cab 3.9L V6 2WD Auto
2006 Dodge Dakota ST Club Cab 3.7L V6 2WD Auto
1991 Dodge Daytona ES 2.5L 4 Cylinder FWD Auto
2011 RAM 1500 Quad Cab 5.7L Hemi 4x4

 

I think we have a weiner for the most Dakota's owned award....

 

Thought Daytona said Dakota...but three Dak's none the less :P