Rise to Fame
While most comedians in 2012 were doing confessional therapy-speak, he went the other direction. New in Town was meticulous, controlled, full of punchlines you could set a watch to, and it found the audience that wanted actual jokes. Five years writing for SNL built the craft. By Kid Gorgeous (2018), he'd won an Emmy and built a following that fills theaters just to hear material they already know.
In the Spotlight
Baby J (2023) was the bet on honesty. He built the special around the intervention his friends staged in late 2020 (they told him it was dinner), two stints in rehab, and the marriage that ended while he was still getting sober. It won him a second Emmy. The wreckage became the most-discussed special of his career. Since then, he's married Olivia Munn, had two kids, maintained sobriety through her breast cancer diagnosis, and launched a live weekly Netflix talk show. The chaos turned out to be the material.
Side Notes
He came up as a writer, not a performer. A Georgetown degree put him in the SNL writers' room before anyone was asking for tickets to his specials. He auditioned by doing stand-up instead of impressions and got hired anyway. His most famous on-screen credit from that era isn't even him: Stefon, the Weekend Update character he co-created with Bill Hader, belongs entirely to Hader's face. He voiced Spider-Ham in Spider-Man: Into the Spider-Verse and made a children's special with Jake Gyllenhaal and David Byrne. The craftsmanship is everywhere. The personal disasters just made it visible.