This Lowkey Ex-Con Is the Internet’s Most Popular Comedian

A couple of years ago, at the age of 49—three decades removed from an FBI drug bust that sent him to prison, and 24 years into his career as an ex-con turned stand-up comedian—Ali Siddiq was still seeking his big break in show business.

Siddiq’s debut special, It’s Bigger Than These Bars, found him back in a Texas jail performing for inmates, but it came and went on Comedy Central after a few airings in 2018. The following summer, NBC put him in primetime where he competed against...