Roy Wood Jr.’s Imperfect Messenger Is Funny, Thought-Provoking, and Empathetic

Roy Wood Jr.’s third stand-up special Imperfect Messenger is a perfectly-titled comedy special for this imperfect time. The Daily Show correspondent opens with thoughts on the last two years changing the context of the question, “How are you doing?” and connects that to a joke that serves as a thesis, or at least a recurring note: we are in bleak times and everyone is trying to find just a little bit of joy in their lives. Over the course of Imperfect Messenger, Wood comes back to this idea frequently.

Wood’s stand-up special talks about the specific circumstances of oppression and marginalization of Black people in the United States without showing disdain for any other overlapping minority groups. I didn’t used to think that was profound, but here we are. Wood talks about racism, of the personal and structural sorts, and even across continents. It would feel like a curse to say he “speaks truly and freely,” because of who that might associate him with, but he does speak honestly and openly.

Comedians sometimes want to shut down any criticism by saying their words are “just jokes,” while simultaneously wanting to be taken seriously as philosophers commenting on current events. A lot of stand-up can take place on a spectrum if you make those two points its poles, rather than an intersection. But who’s to say it’s even that clean a difference? Comedy, like most artistic and creative jobs, requires its artists to pour out of themselves for the sake of captivating and entertaining their audience. If a comedian takes themselves too seriously, this might lead to an over-abundance of what I’ve heard comedians derisively refer to as “clapter,” where people aren’t laughing at jokes, they’re only clapping because they agree. But even clapter exists on a spectrum, from something that’s both funny and true, to something that simply assures the audience member that their preconceptions about the world are correct and someone paid to make them laugh also thinks how they think.

Roy Wood Jr. is a talented comedian, and he’s skilled at crafting jokes that work on multiple levels. And when he tells jokes that could be offensive if taken too seriously, he doesn’t hiss at the audience for pulling back. Yet, I can only remember “awwws” coming once, and they were more groans at the system and expressions of empathy than bitterness or disappointment toward the performer. His jokes aren’t shock-jock comedy – he’s just talking about the nature of racism in the United States. There are jokes about performative allyship, police code words, and legislative ineffectiveness; there are stories about interacting with the police as a young comedian on tour.

He makes nuanced jokes about nuance. He talks about the positive impact police could have by “just doing their jobs,” though he neglects to focus much on their abuses of power. He draws from a broad pool of references so that the show is timely without being so locked-in that it will be no fun to watch in a few years. There’s probably no way for comedy to be fully immune to the ravages of time, but a good enough joke can be resistant to erosion, while informing its audience about the time it was made in.

What probably impressed me the most throughout the set is how he uses call-backs that tie the show’s themes together, like an academic text reminding you how all the points are connected, though much more conversational and not nearly so dry. He also has a clever way of using a sort of murmur/mumble effect to mock people in hypothetical situations, and that adds to his stories and anecdotes, alongside accents and imitations. Wood has the demeanor of a friendly uncle or older cousin; he tells jokes like a storyteller, but without ever sounding like he’s dawdling or rambling. The whole set is coherent and connected.

If I had one criticism, it might be that Wood does not go far enough in some ways, but that has more to do with the range of topics than anything else. I also feel like asking comedians to tell us more about how they feel has proven to be quite the monkey’s paw. He’s a left-of-center-but-not-leftist comedian espousing empathy; maybe it’s as likely as not that, if he was more aggressive, we’d get the radical centrism that always trends toward reactionary politics and, frankly, I think we’ve got enough of those comedians.

A specific instance of not going far enough, in my opinion, comes to his discussion of incarceration toward the end of the show. While I agree with his general appraisal about the value of celebrities using their influence to free the incarcerated, I wonder about how the audience walks away from his retelling of his own brief brush with an attempt to do that. Basically, I don’t think that the personal feelings of a victim’s family are the only important thing at stake when people are incarcerated. Much of Wood’s comedy points to an understanding that the justice system isn’t just, but I think expressions of empathy and corrective justice have to dig deeper than the personal stakes of releasing someone imprisoned for twenty years for being an unwitting accomplice to a murder. Still, I don’t think it sinks the show.

Roy Wood Jr. is more or less content to tell you to try to enjoy life, while poignantly commenting on current events, and that’s pretty good. It’s also a relatively blue performance, but somehow it didn’t feel that way because of Wood’s easygoing demeanor. Even still, he’s a very active comedian—he uses the space and is incredibly expressive, even if he’s not playing jump rope with the mic cord or anything like that.

The joke that drew me to see the show was one that occurred to me before about white actors that play evil people in films about Black stories. It’s a taste of Wood’s sense of humor and gives you some idea of what you’re getting into. The role of entertainment in society was a recurring theme, perhaps due to the inherently reflective and frequently meta nature of making a living telling people jokes about reality. Roy Wood Jr.’s special is about empathy and reflection, and you come away feeling like you were given something to think about, but not that you have new enemies to fight. Even if I came away from it disagreeing in some places, it didn’t leave a bad taste in my mouth. Roy Wood Jr. might be an imperfect messenger, but he’s far from being a bad one.

Kevin Fox, Jr. is a freelance writer and Paste intern. He loves videogames, film, history, pop culture, sports, and human rights, and can be found on Twitter @kevinfoxjr.