Hinchcliffe, known for his edgy humor and his podcast "Kill Tony," referred to Puerto Rico as a "floating island of garbage," a remark that was met with immediate outrage from left-leaning media figures.

On "The Daily Show" Monday night, Stewart showcased reactions from MSNBC and CNN personalities, criticizing the roast comedian’s controversial comment. One of the more prominent reactions came from Mika Brzezinski, cohost of "Morning Joe," who labeled Hinchcliffe's joke as "extremely vile." Stewart humorously noted that "Extremely Vile So-Called Jokes" could be the title of Hinchcliffe's first comedy album.

Stewart acknowledged that inviting a roast comedian to a politically charged rally so close to Election Day might not have been a strategic move for the campaign. Nonetheless, he emphasized that Hinchcliffe was essentially sticking to his brand of humor. To underscore his point, Stewart aired a montage of Hinchcliffe's provocative jokes from the Tom Brady roast, including comments about Jews and black people, followed by Stewart pretending to be outraged.

"Yes, yes of course. Terrible. Boooo!" Stewart exclaimed sarcastically while attempting to contain his laughter. He admitted to finding Hinchcliffe exceptionally funny, even expressing a degree of helplessness over his sense of humor.

Stewart wrapped up with a jab at the Harris campaign, comparing the situation to inviting Beyoncé to a rally without having her perform. This reference was a nod to the recent Harris rally in Texas where the Grammy-winning artist made an appearance but did not perform, disappointing many attendees.

Through his mix of critique and humor, Stewart highlighted the complexities and challenges of merging political events with comedic acts, especially those known for their boundary-pushing content.