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Have a gal like this in your family tree. #1 is a 1928-29 Oldsmobile 3w coupe; #2-#3 while not 100% sure, I believe it's a 1930 Nash. #DavesCarIDService
First one is tough, but it's definitely much later than 1919; cowl vent door, fenders & wheels are consistent with 1930 Buick. Second pic is 1942 Oldsmobile.
Great Grandma is holding the baby in front of a 1959 Chrysler New Yorker
Thank him for his service, but highly doubt it was a WW1 car. Appears to be a circa 1920 Buick, but might be a Jordan. Sedans and other closed cars w/ glass windows were pretty exotic until after WW1.
Not a lot to go on here, but the car behind Mutt & Jeff is consistent with a 1926ish Dodge Brothers coupe
A #DavesCarIDService PSA: if you want me to ID a car, please use the hashtag so I can keep track. If it's been more than 3 weeks since I've responded, tweet request again.

Please note: I prioritize old family photos, abandoned cars and such over attempts to stump me.
There are certain distinguishing characteristics of even very old cars that narrow it down, even with a partial pic; character lines/ embossing, visor shape, etc. If I ever write that book I will elaborate.
And just to be clear, I don't consider myself to be an "expert" on old car identification, just a reasonably competent amateur. I know dozens of people who are far more skilled at this than I am.
anyhoo, back to the IDing: 1965-ish International Harvester
lower left foreground is 1936 Chevy; in front of it is 1934 Ford Tudor; across the street is 1935 or 36 Ford Tudor. Photo is no earlier than October 1935.

Left is 1948-50 Ford F1 pickup. Right is an amalgam of parts; Grille/hood from 1933-37 International Harvester, cowl appears to be a late 40s Willys Jeepster, wheels seem like Nash
This one was a pain to ID, but I believe a 1929ish Marquette. Marquette was a GM make, the the low price "companion brand" to Buick; just as Viking was to Oldsmobile and LaSalle to Cadillac
I'm not great on early heavy duty trucks, but I'll venture a 1928 or so Mack
The beaming newlyweds are with a brand new 1954 Oldsmobile 88
Concluding today's IDs with this patriotic WW2 tableau: Left, 1937-38 Plymouth coupe; Right is a 1941 Ford Super Deluxe or 1941 Mercury.
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