Never mind that they forgot to "stay with it as the years roll[ed] on" (leaving him in the 50s through the entire 1970s; guessing the 50s nostalgia craze fueled by "Happy Days", etc. in the 70s didn't help),
Actually, by 1976 or so they had his teen years in the 60s, as witness this classic page from "Who Took the Super Out of Superman", wherein he meets JFK:
https://www.supermanthroughtheages.com/tales2/whotook/1/?page=3Incidentally, kudos to the great Curt Swan, who nails Kennedy even from behind and above, by recreating his distinctive and unique posture (maybe a result of that bad back of his?). Now THAT is talent.
Forgot about that story (and yes, excellent art from Swan---easily telling it's JFK even with his back turned to us)... though apparently the writers of Superboy's "Adventure Comics" run the following year (in '77) *did*, with the opening-splash-page blurb explicitly stating it took place in the 50s: "The Fabulous Fifties! Dwight D. Eisenhower is president; the New York Yankees are the #1 team in baseball; Lucy is the undisputed queen of TV; and in Smallville, a young man who will someday be the world's greatest hero is already renowned as...SUPERBOY".
I'd forgotten that Superman's "canonical age" was supposed to be 29. I wonder how that came about. Personally, I'd like him to be a bit older, pushing 40 or so (after all, George Reeves was already 37 when he first started playing Superman). In other words, I'd like him to be about my age.
Imagine the Superman-is-29 bit was apparently set in the early 70s, probably as part of the changes (and the new Julius Schwartz-edited books) in the picture I posted above and to make Superman appeal more to youths of the time (by "youthening" his image a bit, even if Swan's artwork didn't make Superman or Clark Kent look that young; though Schaffenberger's Supes seemed closer to the 29 mark). Before Schwartz, Weisinger seemed to portray Supes as in his mid-to-late 30s at least, while post-Crisis comics bumped his age up to 35 starting with 1994's "Zero Hour" storyline.
Supes being 29 never bugged me, though I guess I'm A) close to the age (turned 32 last weekend), B) accept that eventually I'll be older than the characters I'm reading about anyway, and C) given Supes, Batman, and other characters would have to be, well, in their 50s (or older!) to fit in the zillion Christmas stories, presidential elections, etc. shown over their careers, I figure they may as well stay around 30, since they aren't ever going to be shown as aging or anything (Earth-2 and Kingdom Come/alternate future glimpses aside)...
A big part of Superman's appeal to me has always been his "father figure" image, so add me to the list of fans who like him older. Partly this is due to Reeves, but also Curt Swan, who always drew Superman/Clark looking in his late 30s at least.
One reason I never totally got behind Christopher Reeve's interpretation was that he was too young to fit my image of Superman (and, as scripted, still under the thumb of his father's authority). And I REALLY didn't like the Iron Age version, who was not only physically young, but emotionally even younger, making childish mistakes and forever running home to Ma and Pa for advice on how to tell right from wrong.
If you want a *too* young-looking actor playing Superman, try Dean Cain's version...
I never got a strong sense of exactly when Superboy's adventures took place when I read 70s comics (aside from that JFK cameo), and I think that's a good thing. It helped having him live in Smallville, which due to its small-town, agrarian nature would logically not be a showcase for the latest gadgets and fashions anyway. Indeed even in the towns I grew up in in the early 70s it wasn't uncommon to see cars with tailfins still on the road, and older gentlemen wore hats every day just as they had in their youth. Part of the appeal of Smallville was that it was just generically "vintage" without being tied to any particular date.
That's another part of the legend that's gone and can't come back. I don't care how young you are, it's hard to imagine 1989 ever seeming "quaint" or "nostalgic."
Well, guess depends on how old one is---for me, 1989 was when I was starting high school, so it feels like awhile ago to me, plus "quaint" in having fewer gadgets/no widespread Internet use/goofy-looking clothes compared to nowadays, among other things.
But yes, I imagine (particularly for Baby Boomers) it isn't the same as the Silver Age Smallville's setting featuring fedora-wearing men or distinctive-looking older cars, the result of being set at various points in the 1930s, 50s and 60s (1989 = the time when all new cars started to look the same and generic, as "Bloom County" put it at the time). Maybe ironic that the last pre-Crisis Superboy storyline involved Smallville (by that point in the late 60's/early 70's) being threatened with the construction of that modern icon that was becoming more and more prominent in Superboy's era by that point, a shopping mall...
On a final note, assuming Superman were 29 in 2007, a teenaged Superboy these days would be in the early 1990s... wonder what an early 90s Smallville (with a Superboy, vs. the Iron-Age incarnation published at the time) would be like---seeing Clark's reaction to the fall of the Soviet Union or the rise of the Internet (or, in a followup to the shopping mall story, seeing the town threatened by some Wal-Mart-like behemoth trying to move into town) would be amusing...