I think that it`s quite the opposite, Trump was half joking, it`s just that not everyone gets "dry humor" and unfortunately for Trump it`s easily exploitable. Stuart Smalley, on the otherhand making the comments while Clinton was in office, a draft dodger himself, was being a little more serious. In the 2000 pre-9/11 period the Vietnam era Baby Boomers were still solidly in control and their anamosity towards the military was bleeding through. What Franken said in that setting was not controversal at all and got some yucks and nodding of many heads.
There is a generation and Franken was in the midst of it, that "loathed the military" and were not at all bashfull about it. Today after Gen-Xers grew up on Swartzkoff and such are more appreciative of the military. Appreciative to the point of "Idolatry", which is not a good thing that is how we get into stupid wars, we are awestruck by a guy on tv with a chest full of medals that says "we should go to war!". Boomers question whether they may have been wrong avoiding the draft, so to "make up for it" kind of get uber-patriotic, coming I`m sure from their own personal guilt.
When people are awestruck and on a guilt trip they tend to make irrational decissions.
