The sign at the motel in Santa Modesto says that the motel features TV/VCR in the rooms, however this game takes place during the 1950s, long before the VCR was available to the common public.
The game takes place around 1957. However, the drive-in is showing Plan 9 from Outer Space (1957), which didn't come out until 1959.
When Scanned some women say "I'm afraid of Virginia Wolf", as a homage to the film Who's Afraid of Virginia Woolf? (1966). That film was released in 1966 and this game is set in 1957.
The U.S. flag in the game is the post-1960 with 50 stars on it. It is thus incorrect for the 1950s; back then it only had 48 stars.
When Crypto morphs into the Navy officer, the instructions on the screen clearly say, "Morph Into the Navy Warlord." However, when Crypto shows up at the meeting with the other officers, they address him as General. The Navy does not have Generals. Only Admirals. The correct way to address him would be Admiral.