Laughing through the pain: the moments 'The Roast of Kevin Hart' stopped being a joke

Well, well, well … looks like the teacher became the student in "The Roast of Kevin Hart " (whatever that means) and from the first mic drop, you could already tell nobody came to behave.

Let us start here. Every second word out of Kevin Hart’s mouth is “b***h” and “f**k”, and it is evident from the beginning of the special that we are all fluent in his vocabulary now.

Still, somewhere between the jokes and the forced laughter, you cannot help but wonder if we are all just watching a very expensive group assignment that someone decided to call entertainment.

Now I have reviewed Hart before, and one thing that always stands out is how he leans into his own story. The short jokes, the self-awareness, the constant reminder that he is still “that guy” despite everything.

It is a formula that works for him, but at this point, it feels like we are watching reruns of the same punchline wearing different outfits.

Then came Tom Brady (yawn), a known regular in the roast circuit at this point and clearly very comfortable in that space, like he pays rent there. He leans straight into the classic material, dragging out the short jokes about Hart, which at this point feel like they should be retired with dignity.

One of the most repeated themes was Hart’s height, turned into punchlines that kept circling back in different forms, almost like the joke refused to move on.

He also goes for Hart’s scandals, the cheating headlines and the DUI situation, then takes it further by playfully flirting with Hart’s wife in the audience.

It is that very specific roast humour where people are laughing but also sitting there thinking “okay now… did we need all of that”, especially because Brady himself has lived through his own public scrutiny, including very personal controversies involving his family and son, which makes the choice of targets land with a bit more edge than entertainment.

Then came the moment everyone was actually waiting for, Katt Williams and suddenly the room shifted in a way that felt less like a roast and more like someone was about to say what everyone else was tiptoeing around.

Williams did not come in doing surface level jokes. He came in doing true-to-form things, which means saying something funny while also making it slightly uncomfortable in the way only he can pull off.

One of the moments that stood out was when he brushed on Hart’s association with high-profile Hollywood circles, referencing those “Diddy party” conversations that have been floating around the industry discourse.

“Just because Kevin went to Diddy parties does not mean he did something wrong,” he joked, before adding that the real tell is how quiet someone gets when the topic comes up, implying that silence sometimes says more than any punchline ever could. It landed in that space where people laugh first, then think later.

And that is the thing with Williams. He does not just aim for easy laughs. He uses timing, pause and that signature delivery to turn jokes into commentary.

While most of the roast stayed in familiar territory about Hart’s scandals and public persona, Williams leaned into perception, reputation and how quickly narratives stick in Hollywood whether they are fully explained or not.

There was also that underlying tension he brought in, especially given his own history of speaking out against the industry. He did not shy away from it. Instead he folded it into the set, making his presence feel less like a guest appearance and more like a statement.

Tony Hinchcliffe, a prominent American stand-up comedian, was leaning towards a more racial approach, surprise surprise.

He made a George Floyd joke while roasting Hart: “The black community is so proud of you … right now George Floyd is looking up at us all laughing so hard he can’t breathe.”

And, uhm, it was just sad to see.

Behind Hart’s eyes it was very much like a “that’s not funny but I guess I have to laugh” moment. The crowd did not help either. It just seems like these kinds of roasts cross lines, but in the name of comedy it is “okay”.

How exhausting. Boo, Hollywood! Boo!

The rest of the guest line-up largely leaned into familiar roast territory, circling the usual targets around Hart’s height, past scandals and celebrity name-drops.

While the jokes were not identical, many stayed within the same lane of predictable roast themes, with delivery doing more of the work than originality.

Rating: ** significant flaws but some merit.