I've said before that Trump has made comedy very challenging as it reduces late night hosts to gesticulating wordlessly at the latest clip of Trump saying something inane or illegal or outlandishly deranged to the point that it's beyond interesting critique, and it's also eliminated the option of pretending to take it seriously like old school Colbert because that's just not credible, so news cycle driven comedy dries up.
comedy thrives on the unexpected, and while Trump's excesses are often shocking they are rarely surprising, so all you can do is bond over being strapped into this ride for the duration.
I enjoyed watching I Love Boosters and was looking at Boots Riley's earlier movie Sorry To Bother You and found this detail interesting:
Riley has said that the film offers a radical class analysis of capitalism, rather than a specific analysis of the U.S. under the presidency of Donald Trump as some had opined; he wrote the initial screenplay during Barack Obama's presidency, and the target was never any specific elected official or movement, but "the puppetmasters behind the puppets". While most of the final script remained the same, minimal changes were made to avoid appearing to critique Trump specifically, including removing a line where a character says "WorryFree is making America great again", which was written before Trump used the line in his 2016 presidential campaign.
I think that's the key: take the focus (and ideally the oxygen) away from Trump towards issues that predate him and will still be around long after he's gone to the celebrity golf tournament in the sky, then find something entertaining, surprising, and funny to say about them!
