No one here has yet posted what I personally consider to be his cringiest video:
He opens with an intro... You can skip that part if you wish.
At 5:34 he begins filming a random open mic comedian. You can hear his laughter... It's so loud and inappropriate at times. You can tell that he doesn't understand the very nature of humor; he laughs at the completely wrong times. For those of you who are not familiar with the amateur comedy scene, filming peoples' acts is a CARDINAL SIN. You absolutely cannot do that to a comedian, ESPECIALLY at an open mic, when they are trying out new material that they know is likely to bomb.
The woman he's filming hears his maniacal laughter and then notices he's filming her at 6:45 and calls him out for it. The interaction is so cringy, but she handles it pretty well. He DOESN'T STOP until she expresses her discomfort multiple times.
He continues filming every comedian who goes up, and gets called out at again at 14:13. Then, we get to the gold of the video. Tommy begins his performance at 14:16. You seriously need to watch this.
Holy wow, it's cringy. Every single "joke" falls flat. He clearly does not understand even the fundamentals of stand-up comedy.
"So... Obviously you're not laughing at that!" Nice transition.
He starts having what literally looks like an emotional breakdown on stage. Look at his face! Wow, forty seconds of complete silence. There has not yet been even a SINGLE courtesy laugh - something fellow stand-ups are usually more than willing to provide, given that you haven't completely alienated yourself from them by filming them against their will.
He does an impression of a woman who's about to raped that is in the poorest possible taste. Legitimately uncomfortable to watch.
"One thing that's interesting is you can put anything in the microwave besides spoons and tinfoil." That's not exactly a great premise, bud. And now the "physical comedy" begins. The sound effects! Oh my God. What even is this bit? What is he enacting?
DEAFENING SILENCE. This bit about Superman, it's completely pointless and goes nowhere. He's just rambling. Some token joke about Batman/Robin being gay... And now he starts doing (horrible) impressions. They aren't even jokes. He's just doing (very common) impressions, poorly.
And then he plugs his YouTube channel and scampers away.
He goes back to filming another comedian. Stopped watching at this point but I'm sure there's plenty of more cringe in the rest of the video. He is completely oblivious. The least socially aware human being I've ever seen.
EDIT: Just found out he has more stand-up here. Gonna watch now and live-react.
He comes onstage with a megaphone for a prop... Yikes. First bit indicates that he doesn't understand what Viagra is or does. He seems to think it's for making your dick bigger?
He seems to have some of his friends planted in the audience this time, which actually assures it won't be as cringy because they are laughing (seems like they're laughing AT him, not with him... but yeah).
Publicly announces he's a virgin and gets some applause. Claims women can "smell" his virginity; this is a valid comedic premise, actually.
His friends start telling him to "do the weed joke." They are clearly only here because they are ween'ing him. "The weed joke" is just a story about how his friend drops a joint and sets his dick on fire.
He talks about a hypothetical app that teaches you how to give a blowjob. Bizarre.
"I am a bit of a celebrity." Nope. Nah. Not at all. This Google+ bit makes absolutely no sense. So disjointed and nonsensical. When he leaves the stage I get the impression that the MC is fed up with him/is used to him coming out and ruining shows.