Saw his 1st Special - then watched and listened to everything he's ever produced.
This is one of my favorite specials of Toms with the dark, sarcastic, cynical type humor you wouldn't want to watch with your mother... He's worked with so many like-minded comedians and co-produced or assisted in others performances and they're all just amazing, pushing-the-line type humor without crossing it but making the benchmark higher for other comedians. (If that makes any sense).
In comparison I'd say somewhere around: Bill Burr, Chris D'Elia, Chad Daniels and others. (Mainly adding D'Elia in for the likable quality him and Tom both have and how they keep it real with the stories they present. In different ways of course.)
I couldn't recommend Tom Segura more - all of his specials are worth watching, over and over.
Side Note - Not relevant to this Special: Him and his Wife also have a pretty great Podcast (which I usually cannot stand Podcasts) just about things going on and memes, other comedians, world topics and just a lot of randomness. It's called "YourMomsHousePodcast" if you want to check it out.
