This Politico story covers a Norman Rockwell painting just hung in the White House. Obama's too young to remember it, when it first appeared as a magazine cover, so is most of the country.
My family subscribed to the Saturday Evening Post during the 40's and 50's. I looked forward to the arrival of each issue, because I was ravenous for reading material (no TV in those days). A Rockwell cover was usually notable, something even my parents would express interest in and pleasure in. As I remember, he was the only painter/illustrator of whom that could be said. The closest parallel today I can think of is the occasional New Yorker cover, but none of the artists of those covers stand out in my mind. It was a sad day when he left the SEP.
The Problem We All Live With was unusual for Rockwell; he didn't usually comment on social issues (except for his version of FDR's Four Freedoms, but that was before my time). It was also painted for Look, appearing in January 1964. I was in grad school then, so I would have seen it on the newsstand. I remember, I think, believing that it was a sign of "middle America" moving to the left. JFK had been dead a month and a half and LBJ was pushing the Civil Rights Act to honor his memory. (LBJ would go to hell to find some lever to move Congress--as I say, Obama was too young to take lessons.)
When I was young, I used to confuse the Rockwells, because there were two of them: Norman and George Lincoln (no relation), and in those days there was no Wikipedia to refresh your memory as to who was whom. So it took a while for me to recognize that there were two separate people, not one guy who painted well but had evil political opinions. (I've never been good with names.) George Lincoln Rockwell was the founder of the American Nazi Party, which was a bit more anti-Semitic than anti-black, mainly because Rockwell formed his opinions before the rise of the civil rights movement. But he did his best to make up for it by changing the "American Nazi Party" to the "National Socialist White Person's Party."
So the two Rockwell's model the shift in American public opinion during the early '60's: one moving left, the other far right.