I ended up on the Friar's Club roasts of the early Seventies. Although I was a kid at the time, my family would hurt ourselves laughing as titans of comedy mercilessly ripped each other. Dino's drinking problems, Flip Wilson's ethnicity, Sinatra's mafia connection: it was all fair game.
The jokes were cruel, and two-thirds of them would have inflamed a Twitter mob. Yet it was funny because it was done affectionately.
Even today's updated roasts on Comedy Central, which started in 2003, have their hilarious moments. Although they give some of their seats to people peddling their upcoming movie or book, there is still a sense of a good ribbing among friends.
And then Ann Coulter appeared on the roast of Rob Lowe. It was a bad, horrible awful decision all around. Ann had no connection with Rob; she was there to plug her book and said so herself. Coulter, a professional provocateur, is no stranger to stepping into the proverbial lion's den and stirring crap up. It didn't work. Unless the roast planners' goal was to host a Two-Minute Hate, they failed at everything the roast was supposed to be.
The "jokes" were filled with venom and laced with barely-contained contempt. At Coulter's turn the audience members sat stone-faced when they were not shaking their heads.
This did more damage to the roasts themselves than to Coulter. Absent of affection and camaraderie it was a cringe-worthy hate fest.
Fast forward to the White House Correspondent's Dinner. A good media should have an adversarial relationship with politicians (forget the eight year hiatus for a moment). Trump, for his part, has fanned that contention and even made it personal, culminating in poking them by not attending the dinner.
Trump was probably wise to not attend. After Seth Meyers' savage and painfully unfunny mockery of Trump in 2011, Trump could have expected more of the same.
To paraphrase David Marcus at the Federalist, they should not have roasted Trump there at all. Even worse than a cold mockery is one done in absentia. Hasan Minhaj was likely selected to be a thumb in Donald's eye: a Muslim from one of the most partisan fake news shows on television.
Most of the humor was unfunny on its own, but like with Coulter on the Roast, the hostility drained what humor there might have been. And again, like in Comedy Central's case, it was also damaging to the roasters. A sneering laugh at a person the media clearly dislikes does nothing to rehabilitate their damaged credibility, even if it gives them momentary satisfaction.