1. 2003 Cadillac Escalade ESV
What did you expect? Is there a more perfect car to represent Tony Soprano himself? The transition from Suburban to Escalade was no coincidence. No longer was he remaining inconspicuous in his Suburban, he was the boss now and he wanted people to know it. He also ripped that "GPS shit" out.
2. 1997 Lexus LS400
One of the most memorable cars Christopher Moltisanti drove in my opinion. I mean a "kid" driving a $60,000 Lexus. If that doesn't describe Christopher's insecurities and yearn to be at the top I don't know what does. It's a great car for running people over, and plenty of trunk space.
3. 2002 Maserati Coupe
"Johnny Sack" always dreamed of owning a fine Italian sports car, so he bought this for $100,000. Not really what everyone envisions a fine Italian automobile, and I think that was the point. Who would buy that when you could have a Ferrari 360 Modena like Doug DeMuro? I guess buying a Maserati marked the demise of Johnny.
4. 2003 Cadillac CTS
Sure Paulie's Eldorado fit his stigma pretty well, but the CTS is my favorite. Just watch it destroy Christopher's yard, his past FWD Caddys would never look as good doing that.
5. 1995 Lincoln Town Car Signature Series
Carrado "Junior" Soprano loved his Lincolns, he owned a Continental shown in a flashback. He was boss for a moment and the Town Car represents the "old school" boss. Most importantly it was old, he never bothered for a newer generation because this one represented him.
6. 2000 Mercedes-Benz E320 s210
Because, wagon. Carmela was classy and I couldn't picture a better vehicle for the wife of a mobster.
Ranked by: my favorite, ability to fit character, and usage.