I think Don is heading for suicide. He's in metaphorical free-fall and I predict he will be in literal free-fall. This show will end with the opening animation coming true.
At some point The Simpsons producers were considering spinning off Troy McClure with a live-action show starring Phil Hartman. God I would loved to have seen that!
Some of these must be later than the 60s because that guy is reading National Lampoon from August 1973. You can clearly see the cover (which was painted by Frank Frazetta).
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