Once the clock struck midnight on Donald Trump’s 100 days in office, Stephen Colbert’s claws came out. He delivered his most vicious attack on the President to date during the monologue of Monday night’s The Late Show with Stephen Colbert, using language many were shocked to hear come out of the late night host’s mouth — including a derogatory slur many consider to be homophobic.

Colbert’s 12 minute monologue (!) began by addressing Trump’s rally in Pennsylvania over the weekend and and the handful of interviews he granted, singling in on his interaction with Face The Nation host John Dickerson. Trump wasn’t so quick to offer up answers to many questions, including one about his taxes, and told Dickerson he refers to the Sunday morning news program as “Deface The Nation.” To this, Colbert offered, “Donald Trump, John Dickerson is a fair-minded journalist and one of the most competent people who will ever walk into your office, and you treat him like that?” Colbert also stood up for his CBS colleague, saying Dickerson has “way too much dignity to trade insults with a president of the United States to his face.”

However, Colbert admitted, “I sir, am no John Dickerson” —quick aside: Don’t you just HATE when people use the word “sir” as a means to levy a condescending attack?— before he unleashed a string of insults, including “Mr. President, I love your presidency, I call it ‘Disgrace The Nation,’” and “You’re the ‘presi-dunce’ but you’re turning into a real ‘prick-tator.” (Fast forward to roughly the 10:25 mark of this video.)

But then he went about as brutal as we’ve ever really seen Colbert get, continuing, “Sir, you attract more skinheads than free Rogaine. You have more people marching against you than cancer. You talk like a sign-language gorilla that got hit in the head.”

And then Colbert finished it off with the most scathing line of them all: “In fact, the only thing your mouth is good for is being Vladimir Putin’s cock holster,” which elicited gasps from the studio audience.

Lobbing jokes at the President of the United States, be they Democrat or Republican, is a time-honored late night monologue tradition. Partisan critiquing of the President’s policies is a relatively new facet of late night monologues (at least those on broadcast TV), but one that has undeniably led to increased ratings and relevance for hosts like Stephen Colbert, Seth Meyers, and others. However, using a derogatory, homophobic slur like “cock holster” to denigrate the rightfully elected leader of our nation seems like a step way, way too far. In a misguided attempt to defend his friend and fellow Tiffany Network employee, Colbert’s blustery bravado regressed from pointed punnery into nasty schoolyard bullying, embarrassing himself, his staff, his network and everyone that watches his show.

Will Colbert get suspended for crossing the line like this? We strongly doubt it. However, that doesn’t mean that he should simply get away with it. The right thing to do in a situation like this would be for Colbert to apologize for getting caught up in the heat of the moment and taking things too far. We’ll be tuning in to the Late Show this evening to see if he recognizes the error of his ways. Disagree with the President all you want, “Sir,” but try to do so in a manner that’s more becoming of someone of your immense talent.