This next car isn't the car that Robert De Niro's character (Ace Rothstein) drove in Casino, because that was an El Dorado...but it probably has similar bomb absorbing underbody panels and is so seriously gangster that I can't help but smile. This is the kind of car that a gangster like Vito Genovese or Crazy Joe Gallo would drive. Find this 1972 Cadillac Coupe DeVille offered for $6,500 in Pasadena, CA via craigslist. Tip from FuelTruck.
Back in 1984, Cadillac was not trying to ape German car makers to make the fastest sedan to run the Nurburgring. They primarily focused on making large cars that got middling better gas mileage than the parade floats of the 1970's. No one would mistake a Coupe DeVille for an Audi or BMW back in these days. Today's feature has a late model LT1 engine swap though the seller here is optimistically thinking this 5.7 came from a Vette as the engine cover looks like it was from a late model Fleetwood/Roadmonster/Caprice. Either way, the current engine provides significantly more motivation than the stock unit. Find this 1984 Cadillac Coupe DeVille for sale in Columbus, OH for $5,500 via craigslist. 
How does this sound to you? Red paint, red landau roof, red leather seats, red carpet, red dash, and red steering wheel. This downsized 1977 coupe is to the color red as golfer Ricky Fowler is to the color orange. Find this 1977 Cadillac Coupe de Ville for sale for $12,500 via Northwest CT craigslist.