One for the annals of #DavesCarIDService: these patriotic Chicagoland lovebirds are wooing and cooing on the running board of what I believe is a 1910-12ish Stearns-Knight touring car, but not 100% certain.
For the record Stearns-Knight was subsumed into Willys, which later became part of AMC as Jeep, which is now part of Chrysler, so trace amounts of Stearns-Knight DNA are still available in the new car market.
No, the tipoff for me here was the 10-spoke wheels (most makes had 8, 10 or 12) and low slung gas headlights. It's certainly pre-1915, as by then almost all cars had cowls rather than the flat firewall directly behind hood.
There are certain visual heuristics you can use to narrow down the year range of a car to a 3-4 year window, which makes it easier to ID the make. Biggest challenge is pre-WW1 due to the sheer number of car companies that existed.
Sorry, can't help you here; it's a stylized woodcut print illustration of a circa 1926-31 sedan but not of any make in particular. If it was meant to be a particular car, the artist wasn't skilled enough to convey it.
1949 or 1950 Ford Custom 4 door sedan
Tough call, but roof line, rear window and cowl vent are also consistent with a 1949-51 "shoebox" Ford
This square-jawed WW2 swabby returned home to his 1937 Plymouth
A great pic, but long after the war, featuring 2 of the most iconic tailfins of all time: Harley Earl's 1957 Chevy Belair (foreground) and Virgil Exner's "forward look" 1957 DeSoto Fireflite
Man, I love that pic. It looks like they're gonna smoke pipes and discuss Norman Mailer over cocktails & bebop jazz in a sunken living room with space age fire pit
This crew of Iowans is atop a 1936 Ford coupe; to the right is a 1937 Ford sedan. License plate is 1942 Boone County Iowa, in the early stages after Pearl Harbor.
This follow up ID request shows a 1937 Ford sedan, which is likely the same car in the previous pic.
1961 Buick Flamingo GM concept car, based on the 1961 Buick Electra 225. A full sized Barbiemobile customized with Milady in mind, it never became a production model.
One over-the-top appeal to the feminine car buyer that did make it to market was the 1955-56 Dodge La Femme, which came with its own matching pink-white-black purse. Didn't sell well, but is fairly collectible today. 
On the other end of the gender spectrum, in 1955-57 Dodge offered the Texas-only Texan model, for two-fisted Texas cowboy Texans in Texas
For full-out Texas appeal, hard to top the 1956 Ghia-designed Chrysler/Plymouth Plainsman concept station wagon, complete with cowhide interior. Just the ticket for a 200 mile drive around your property to check on your oil wells.
An only-a-mother-could-love 1948-50 Packard Custom 8 limo
1951-53 Dodge B series pickup, and an awesome picture of your dad in his pith helmet. RIP
First is kinda tough call, I believe it's a 1931 Graham with 1938 Utah plates. Second is easy, 1936 Ford. Photo is 1944 - "V for Victory" tag is for 1943, windshield sticker is for 1944. California went to year plates again in '45
these tow-headed urchins are with a 1930 Chevy Universal 2 door sedan.
this dapper gent is with a 1950 Oldsmobile Rocket 88
Not gonna try to ID individual cars in this, but collectively they suggest 1923-25; mostly touring/open cars, and closed cars have tallish "phone booth" profile
Pretty sure a circa 1908 Packard touring car, I'm guessing from pennant it was used for tour excursions in Yellowstone.
Looks like these show-stoppers nearly caused a 1937 Chevy to take out a light pole
A 1966 Plymouth Barracuda with its ridiculously expensive to replace rear window. This style of Barracuda debuted in 1964, and was arguably the first 'pony car,' predating the Mustang by a few months
1957-ish Austin FX3, widely used in the UK as taxi cabs
Gonna close off today with this delightful slice of Americana. Grandpa's truck is a 1930 Ford Model AA, but with a few upgrades - BLC headlights and 18" KH wheels instead of the stock 19".
PS - going forward I'm going to concentrate on ID requests for cars in old family pics, rather than found-on-the-internet / ability challenges & the like. These are more fun and tell cooler stories.
