IMO a great example of this freedom is the Stephen Colbert character roasting Bush in person at the 2006 White House Correspondents' Dinner. This was when 9/11, Iraq war, Guantanamo Bay, Katrina, etc. were on peoples' minds at the time.
I cannot fathom how you think this is "not that special". Of _course_ it's a bigger deal to be allowed to roast the president to his face and an audience consisting of his strongest supporters than to be critical of the government to a (probably smaller audience) of people who already agree with you.
If this happened in the current administration it would be met with a severe character assassination by the president, Fox News, OAN, etc. His ego is simply too fragile to handle any sort of criticism.
Of course the only way it could happen in the first place would be to trick them into thinking it wasn't going to be a roast in the first place.