While the "entry-level" Cadillac 2-door for '69, the Calais, was pretty slick, the one we saw in this series has clearly seen better days. But when you're talking serious Cadillac sporty luxury for 1969, you really need to think more in terms of the Coupe de Ville convertible. This example, spotted mere yards from the very rough '69 Volvo 144, is in very nice condition, which is impressive for a convertible that parks on the street every day.
Although Fear and Loathing in Las Vegas was set in 1971, it's possible that the Great White Whale Cadillac rented by Raoul Duke and his 300 Pound Samoan Attorney was in fact a '69 just like this one. I should have checked the power windows to see if they jumped like frogs in a dynamite pond. I could tell that the tires were too soft just by looking at them- the fronts are supposed to be tight as snare drums.
All the Iggy Pop ads in the world can't make up for the fact that GM no longer gives that special Cadillac aura to its Cadillac-branded vehicles these days; sure, old men bought them in 1969, but they were hardassed, cigar-chewing old men with style. Note the Alameda Naval Air Station sticker on the front bumper; this car is likely owned by a retired officer who stayed in Alameda for retirement after his days on the Enterprise or Coral Sea were over.
The 472-inch V8 under that big ol' hood is actually capable of getting this monster moving quite well. As always, we recommmend Cherry Bombs!