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Time to fire up the ol' #DavesCarIDService identificationator mosheen
Too bad that many vintage clown-around snapshots were weeded out of the drugstore prints. Luckily this one survived, featuring Great Gramps doing his baggy pants routine in front of a 1941 Buick Super Sedanette.
Another high spirits fun-time shot: there's enough visible here that I can confidently say that Ida is sending love to Sweet Vernice and Ed from the snowy fender of a 1928-29 Ford Model A coupe.
Gotta say I miss those old-timey meat & potatoes names; Ida, Vernice, Lucille, Vivian, Ed, Vic, Al, Gus. Kinda proud to have a 6-year old Edie (Edith) and 8 year old Roxie among my nieces.
This Kodachrome features two towheads posing in front of a 1950 Studebaker, also made in Northern Indiana.
It's a Studebaker Double Feature Sunday! The parking lot of pseudo-rustic Sleepy Hollow includes a 1949-51 Studebaker Champion 4 door sedan and pretty sure a 1952 Pontiac "tin woody" station wagon.
What the hell, let's make it a Studebaker Triple Feature with this 1947-48 sedan at the weenie roast.
quick note: Studebaker got a jump on the Detroit Big 3 with the first all-new postwar car designs from the dashing and dapper Raymond Loewy, father of industrial design. Loewy & Associates would go on to create several gorgeous designs for Stude, like the Starlight and Avanti.
Loewy was a fascinating character, a Frenchman who came penniless to the US after WW1. Besides designing planes, trains, and automobiles (and tractors and appliances) he created some of the most enduring corporate logos of all time.
A bit of a challenge here, but I believe the car behind these New England toddlers is a 1940 Pontiac
I dunno, a Linguini Fromagenador GTZ? Supercars / Hypercars aren't really my bag, and I've lost track of all the ones that've come out lately. Perhaps somebody more into that sort of thing can help you ID.
If my squinting is correct, these folks stopped for a photo op on a road trip in a 1954 Chevy Bel Air
Dad's chariot here is a 1946-48 Nash Ambassador.
That's quite a pompadour on Dad, and his car is a 1949 Chevy Deluxe coupe; both are worth of pride and joy.
I spy the remains of a 1970-72 Chevy Chevelle 2 door hardtop
This terrific pic feels like a still from the Last Picture Show. The pickup here is a 1937 Ford, car in front is a 1930-31 Ford Model A Tudor.
A notoriously horrible pre-Fall of the Berlin Wall Trabant station wagon; could be anywhere from about a 75 to 88 model. I wonder if Fahrschule Bahls are as delicious as Schweddy Balls
*a little googling reveals that Fahrschule Bahls is a driving school
You and Sis are hugging against a 1962 Oldsmobile 98
Behold the mighty tailfins of a 1957 Lincoln Premiere 2 door hardtop, sporting a nice custom paint job and spider caps
1946-48 Ford Super Deluxe woody wagon. These were the last of the "true" woodies, where nearly the entire body was tree-derived.
I'll tackle the easy ones first:

2. 1942 or 46-48 Chevy Fleetline
3. 1935 Ford 5 window coupe
4. 1941 Ford Tudor

1. is a real challenge, will have to consult my notes. Certainly no newer than ~1905.

This one is a real poser; very ornate, open radiator, left hand steering wheel rather than tiller. Best I can guess is a circa 1903 Packard, not a lot of confidence though.
Probably not the owners of the car; automobiles were so new at the time, they would tour county fairs so people could pay to get pictures of themselves in one of those newfangled horseless carriages. Likely the story behind this image.
1962 Ford Fairlane 500, sporting a Thunderbolt style bubble hood
not much to go on here, but I'll venture 1930-31 Ford Model A pickup
A couple of 1917-23 Ford Model T touring cars; top down to the left, top up on the right.
These fellas were Mopar men; left is a 63-65 Plymouth Valiant, right is a 68 Dodge Coronet.
In honor of Mother's Day, let's turn the #DavesCarIDService Identificationator on some mom & grandma pics. Behind Gotham Great Granny here are a 1935 Ford cabriolet and a 1936 Ford Fordor.
Grandma here is beaming with pride from a 1954 Plymouth.
Mother & child here with a 1946-48 Chevy Stylemaster.
Having a hell of a time with this one due to fender trim, taillights, and gas cap location. Running boards, exposed hinges & unsplit rear window put it solidly in 1939-41 range, but having trouble with make. I want to say 40 Olds, but it ain't.
Grandma's grocery getter was a 41 Ford Fordor.
Grandma & her offspring are with a 1949 Plymouth, and judge by your dad's size and birth year, probably a brand new one.
This successful first date was in a "Forward Look" 1957-59 Mopar, and best I can tell a 57-59 Dodge 4 door hardtop.
Closing out today's edition of #DavesCarIDService with this Mother's Day smokeshow from the Dazed & Confused era: Mom & Aunt Sis here are with a 1969 Mercury Marquis. #AlrightAlrightAlright
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