I made a lot of Facebook posts expressing my enthusiasm for The Nightly Show with Larry Wilmore when it started on Comedy Central. Those first few weeks were pretty interesting. While they were constantly experimenting with the format, it was generally funny, and it seemed like it had potential.
Over the course of a year and a half, I slowly lost interest. I can't exactly tell you what happened. I was still watching it maybe once a week, but not religiously as I once had. I think that maybe the show was too tightly focused on a subset of race issues. It's not that they aren't important issues, but they aren't really funny. I remember a number of shows where he would finish the A-block, and I would be kind of angry or depressed in the way that I would be by watching news. That's probably not what you want out of a comedy show.
Politics in the context of comedy works so well that Jon Stewart did it for more than a decade and a half. Social issues, while often made political, don't work as well with comedy. I think that put Wilmore in a difficult position, because he was often quoted as saying that he wanted to give a voice to people who didn't have one in late night TV. It probably doesn't help that Trevor Noah's Daily Show, while also not scoring great ratings, has managed to be consistently good, so having to follow it isn't easy.
Wilmore has a series of TV successes as a writer and show runner, going as far back as In Living Color and as recent as Black-ish, including an Emmy for The Bernie Mac Show (I miss Bernie Mac). He'll have no issue working in the business, but I feel bad for his crew. Entertainment is a brutal business.