He may be riding high with the success of his last film, 'American Sniper', even if some of the more demented critics seemed to think the movie was piece of racist propaganda up there with the likes of 'Triumph Of The Will' and 'The Birth of a Nation'.
But now Clint Eastwood (pictured in 'Dirty Harry') is fighting a foe far more insidious than any villain he ever encountered on the big screen - the Social Justice Warriors.
Appearing at an American awards show on Saturday night, the 85-year-old icon joked about athletes who have become Hollywood stars: "Like Jim Johnston and Caitlyn somebody."
Now as jokes go, that's hardly cutting edge. But any reference to the reality star formerly known as Bruce Jenner that doesn't explicitly applaud his decision to transition to a woman is now classed as some form of a hate crime.
The television network which hosted the event, Spike TV, immediately issued a statement saying the gag would be cut from the transmitted version of the ceremony and have apologised for "any offence caused".
The absurd cowardice of this reaction is made even more baffling by the fact that the actual name of the awards show was 'Spike TV's Guys' Choice Awards' - a celebration of American masculinity which has now been forced to apologise for comments made by the most unashamedly masculine director since John Ford.
The reaction came thick and fast, with the emphasis on the former.
Feminists, transactivists and the usual motley crew of people who like to be offended by even the most innocuous joke have accused Eastwood of everything from 'transphobia' to - and this one is a real stretch - 'homophobia' and have demanded that he also apologises, which would really be a scandal. What's concerning about this row isn't that an ageing director had a muddled pop at a he/she, but the fact that these people think they have the right to decide what the rest of us are allowed to say and woe betide anyone who doesn't sing from the accepted hymn sheet.
The simple fact is that Bruce Jenner, like Frank Maloney before him, decided that he wanted to be a woman and, to his credit, started the process in public rather than behind closed doors.
But once you decide to conduct yourself and your transition so openly - Jenner has that 'Vanity Fair' cover, and his own E! reality show, 'I Am Caitlyn Jenner' in the works - the idea that you are then immune from a bit of harmless ribbing is absurd and dangerous.
It's dangerous because it aims to present certain sections of society as a protected species who must be treated differently to everyone else.
Isn't the whole point of acceptance and tolerance built on the premise that we are all equal and therefore jokes for one section of society should be applied to another section?
Eastwood made a joke about Jenner. Snoop Dog made a joke about Jenner. Drake made a joke about Jenner.
The chances are that you have heard at least one gag about Jenner - these aren't motivated by hatred, rather they are a response to something which is being shamelessly played out in the full glare of self-sought publicity.
It doesn't matter if you think gender is just a societal construct (it's not, of course, but that's a piece of logic for another day) or whether you think he's some degenerate for making his choice, because ultimately, it doesn't really matter what any of us think - this is his business and as long as he's using his own money to pay for his procedures, it shouldn't concern us.
But by choosing to go down the road of maximum exposure and self-promotion for financial gain (he's not doing those TV specials for free), he is as much a legitimate target for comedy as anyone else in the public eye.
It's interesting to note how many of Jenner's earliest cheerleaders were quick to distance themselves when he announced that he was a proud Republican - perhaps the only behaviour that's seen as a perversion in Hollywood.
But as long as he chooses to make a deliberate spectacle of himself, he remains fair game for gags and the idea that people can't make a joke about it is yet another example of the suffocating instincts of those very illiberal liberals who want to control the way we speak. Because they know that once they've achieved that, they can control the way we think.