I'm going with 1964 Plymouth Valiant Signet convertible on that first one.

On the Cadillac, do you have a better shot of the rear end? If I can see its tail fins I can determine for sure whether it's a '59 or '60. Right now I'm leaning toward '60.

In that bottom photo, I'm thinking the one on the far left is a Mercedes wagon.
Looks like an '80s vintage Lincoln Town Car on the rack.