L-R: 1956 Dodge Lancer, 1960 Cadillac Sedan DeVille, 1961 Cadillac Coupe DeVille convertible. Go Colt .45s! #DavesCarIDService
1956 Ford Fairlane Sunliner
That would be the immortal Iowa-born custom car builder-painter-pinstriper Dean Jeffries; car is a customized '46-48 Merc with 56 Ford grille insert & seaweed flames; unfortunately I cannot ID the badonkolicious fender candy
You may best know Dean Jeffries as the creator of the Monkeemobile (George Barris, bless his heart, often claimed credit for other people's work) 
Car on far right is 1950-51 "bullet nose" Studebaker Champion; just around the corner is 1952 Chevy Styleline. It was Dean Drug when I was growing up. There's a chance my 13 year old mom was inside at the Toller's soda fountain.
1940 Plymouth coupe (Dyersville btw is home of Field of Dreams, as well as Ertl diecast toys)
1946-48 Chrysler
1941 Chevy, and A+ hat on Gramps
Definitely not a Ford, but unfortunately not enough info for me to do a positive ID
Another tough one, I'll make a stab at 1946 Nash, but with little confidence. Body shape says early postwar GM, but taillights say no
L is 1959 Mercury, R is 1961 Mercury. Being a landlubber I can't ID the boat, but I'm guessing a Mercury Marine motor
1960-64 Chevy Corvair; across the street is a 1960 Chevy Parkwood station wagon and a 1962-66 Chevy truck
1960 Pontiac Safari station wagon
1928-29 Ford Model A roadster, and Gramps' shiner illustrates why old-timey catcher's gear were called "the tools of ignorance"
Bathing beauty Grandma is posing in front of a 1927-ish Hupmobile touring; can't help you on the other car
1940 Plymouth
1928-29 Pontiac
1. 1947-48 Ford
2. 1957 Chevy
3. 1942 Ford
2. 1957 Chevy
3. 1942 Ford
1936 Hudson Terraplane
1934 Chevy Sedan
1940 or 41 Hudson
1937 Ford Deluxe Tudor
That's it for #DavesCarIDService today, I'll be back on the case tomorrow.
