The first is a '48ish Mopar. Looks really similar to a DeSoto Buisness Coupe I've lusted after for years.
I'd say a '42 Chrysler, without looking in my book, and a '59 Studebaker Lark wagon. Edit: And I was dead on with the Chrysler. Not sure what model but the coupes were pretty rare in any of the 4 model series Chrysler offered. The 3P coupes, they only made about 1000 of total all four combined.
Nice! There's a photoshop post floating right now with a very similar Chrysler chopped as a taildragger. They really do have the perfect lines.
The one on the trailer is either a 1942 Chrysler business coupe or a 1942 Chrysler club coupe. Both are series C-34S Royal. 479 bus coupes were produced. 779 club coupes were produced. Bus coupe weighed 3331 lbs and cost $1075. Club coupe weighed 3406 and cost $1168. Rare cars. Other car looks like a 1960 Studebaker Lark
Barris did a '41 Chrysler 3-window a few years ago, calls it the "City Coupe" Definitly not my cup of tequilla....
If they are both yours id say congratulations on some nice finds. That mopar has some intresting trim treatment
That trim's probably big money to the guy who needs it. Until you find him, though, it's only worth maybe $500 if it's good. The Stude assuming the front clip is original I think 59 and 60 have dual lights and 61-up have quad lights. But it looks just like the '59 we had a couple years ago. The whiskers are a prewar thing, Hudson did the same thing on it's '42s, several stainless bands down low all around the car.
The Coupe is a 42 Chrysler Royal Business Coupe. The Club Coupes had 5 windows and a back seat. Six cylinder.
This 42 is from the LeMay collection. http://images51.fotki.com/v1549/photos/5/1510085/7780042/1942ChryslerCoupe-vi.jpg
This '59 Larkhas tailights that looklike the wagon in the picture. My current '63 Lark has round tailights. Not sure when they changed. Newyorker sounds right o the headlights so maybe the tailights changed ay the same time
In 1942 Chrysler did not make to many coupes. The most common is the Windsor that they only made 1,713 of.