Kicking off today's #DavesCarIDService with some vintage beefcake: #1 is a 1939 Ford Tudor; race car is 1923-25 Ford turtle deck T roadster on narrowed A rails, hairpins, 31 A radiator shell, K-H wires, A/B flathead 4, probably Winfield 3 carb intake
1936 Ford with modified 1935 Ford grille, and various JC Whitney chrome dressup parts (like headlight eyebrows), maybe a wolf whistle horn
Don't go on the road without one 
2010 or so Cadillac CTS, disguised as a 1956 Chevy Nomad
1937 Buick, and I wanna party with this crowd
1931 Ford Model A coupe
windshield angle, door shape, crease along lower body, position of door to wheels
Here's a 2011 Cadillac CTS to illustrate why it's the basis of this 1956 Faux-Mad
1959 Ford Country Squire wagon
1946-48 Chevy, shaved chrome & door handles, modified Cadillac sombrero hubcaps with I think 49-50 Ford dog dish inserts
1938-40 Ford Tudor
Left is 1941 Buick convertible, right is a 1917-23 Ford Model T touring
1946-48 Nash 4 door sedan
Car behind them is a 1941 Oldsmobile; not a lot to go on for the other car, but bumper and fender seem to be 1936-38 Chevy
1933-34 Buick 2 door humpback sedan
1934 Chevy, and I withdraw my previous ID of 33-34 Buick; it is the same car. I had previously thought humpback body style wasn't available on Chevy in '34
Nearest car in the pic is 1941 Chevy
1934 Duesenberg J with LeGrand coachwork; 1934 Bugatti Type 57 Aerolithe. Pic is inside Jay Leno's garage, where I had the privilege of seeing both cars in person.
Dad is squiring Mom in a 1957 or 58 Dodge Coronet 4 door hardtop
1930 or 31 Cadillac V16 Fleetwood
1940 Buick, 1941 Pontiac Torpedo fastback
1963-ish International Harvester panel truck/paddy wagon
It's certainly not an Indian; handlebars and front forks suggest a bicycle-to-motorcycle conversion, a la Whizzer. May need some motorcycle experts to chime in here.
1930 Ford Model A roadster pickup, sans doors
The two cabs in glamorous downtown Des Moines are a 1938 Plymouth and 1940 Plymouth; van is a 1940 Chevy Dubl Duti
Based on gas pumps, cars, and signage, I'd say around 1935-36
Surprise! Despite the Chevy spare tire cover, the transverse rear spring indicates Ford Model T touring, rectangle rear window says 1924-27
Car in the entry is 1917-23 Ford Model T, unfortunately not enough visual on the others for me to positively ID
1946-48 Nash Ambassador
on left is a circa 1920 Oldsmobile. Could have become Beverly Hillbillies truck!
On right is a 1933 Dodge 1-ton, with a railroad conversion. Note single headlight, cow catcher, and locomotive steel wheels
On right is a 1933 Dodge 1-ton, with a railroad conversion. Note single headlight, cow catcher, and locomotive steel wheels
fun fact: the Beverly Hillbillies truck was a modified 1921 Oldsmobile roadster
Last one for the day: overdue thanks to @Harry_Bergeron for solving last week's mystery of the Dutch Beach car
