Looks like the new '59 Ramblers and Cadillacs are in! Looks like if they would have trimmed the fins on the Caddies, they would have fit under that bridge! : )
I didn't know that Phillips 66 used the orange signs that late or that the HC signs were still in use. I did see the DX signs that I grew up with.
I kept watching to see if I recognized anything since I've driven Iowa 330 quite a bit which runs on a section of old US 30, but they didn't show any of that section.