A 1980's movie called Explorers uses a drive-in during a scene where the 3 stars test fly the spaceship they make and accidentally fly it in front of the screen during a drive-in movie. It's a space movie and some know-it-all says "Ugh, that looks SO fake!" and then their ship turns and almost hits the guy, then crashes into the concession stand.
Phone Losers did a writeup on this awhile back, with a picture of one of the newer attempts. Nobody can seem to beat that 50's record though. And the new phone booth didn't even have an actual phone in it.
http://www.phonelosers.net/a-bunch-of-shitbags-try-to-stuff-themselves-into-a-phone-booth-the-same-bunch-of-shitbags-fail/