Stream It Or Skip It: ‘Chris Redd: Why Am I Like This?’ On HBO Max, If Therapy Makes The Comedian This Exuberant, Keep It Up

Chris Redd’s life has seemed even more made-for-TV even just since he recorded his first hour comedy special for HBO Max. Redd announced he’d left Saturday Night Live after five seasons, we found out he was dating Kenan Thompson’s newly divorced ex-wife in the same announcement, and just last week, someone sucker-punched the comedian outside the Comedy Cellar in New York City. What else might we learn from an hour of revelations from Redd?

CHRIS REDD: WHY AM I LIKE THIS?: STREAM IT OR SKIP IT?

The Gist: At 37, Redd finds himself asking the titular question right at the top of the hour, and if the answers don’t come quite as fast or as neatly as you might anticipate, well, then, join the club.
After all, Redd is the guy who I tapped to be an SNL star a year before he officially joined the cast! While behind-the-scenes dealings conspired to make my timing wrong, I still knew what I was talking about when describing Redd as a star in the making. Within a year of him joining SNL, he won an Emmy for co-writing the Outstanding Original Music and Lyrics for “Come Back, Barack” (performing it on the show with Thompson and guest host Chance the Rapper). Redd also co-starred on two seasons of Thompson’s Kenan on NBC, which found the duo going bicoastal during the pandemic. None of that really comes into play in this hour, however, because answering why Redd is how he is requires reaching back further into his Chicago upbringing, the dreams he had before comedy and acting, and how he wasn’t built for a life of crime like some of his neighbors and relatives.

What Comedy Specials Will It Remind You Of?: Conan O’Brien’s Team Coco produced Redd’s hour, but it’s got very little in common stylistically or thematically with Team Coco’s previous two HBO Max hours, for Beth Stelling and Moses Storm. What all three comedians do share is an exuberant stage presence, an ability to connect with their audiences and a gift for joke and storytelling.
Memorable Jokes: Redd’s chunk about going into therapy during the pandemic has plenty of great lines, some of which made it into the trailer, such as how he previously dismissed therapy as only for white people before realizing: “Oh, it’s for people with money and time. White people just had that first.” A simple observation about only knowing his therapist from the torso-up on Zoom leads to a fun section in which he wonders how he’d react if he discovered she didn’t actually have legs.

You’ll also get to watch Redd re-enact his very brief misadventure as a drug dealer.
He spends much more time recounting one very brief misadventure after taking a weed edible, showing us all of the varied ways he acted out on his impulsive emotions and thinking. This routine becomes even more memorable when the crowd starts getting involved. After describing his interactions with fellow passengers in the airport, waiting for the pilot to show up late, then getting stuck on the tarmac, a heckler in the back shouts the name of a different airline. “Do you think that was my problem?” Redd quickly responds. When he tries to engage with the audience member, someone else heckles her, which enlivens Redd even more, before he finally segues back into his story.
And in a complete coincidence, he also shares about two other times he’s gotten whacked in the face or throat.
Our Take: There are a couple of other HBO specials in the past year, perhaps even more similar to Redd’s, in which the comedian talks about therapy and working on their inner selves, all while handling an audience that definitely wants to participate in the process. Jerrod Carmichael’s Rothaniel and  Yvonne Orji’s A Whole Me spring to mind.
And yet Redd exudes so much more energy onstage and control over his audience, making you feel like you wish you were in the room to fully catch the infectiousness of the joy he’s spreading.
He’s more than willing to engage the crowd, to the point where the production offers both split-screen and captioning at times. Another sign of how TikTok has influenced old-media screens?
People may have been surprised to learn this fall that Redd wouldn’t return for a sixth season on SNL. But as he addressed this crowd (perhaps knowing he’d leave but not having announced it yet): “People think I’m living my dream because I’m on SNL,” adding “I’m living white peoples’ dream.” He explains: “I’m grateful. I’m blessed. It’s changed my life.” But do you think he’d still be 5-foot-6 if he were living his dream???
While Redd never made it to the NBA, he also never made it as a drug dealer or as a gangster, but he came awful close to achieving his rap dreams with a co-starring role in Popstar: Never Stop Never Stopping and he is an Emmy-winning lyricist. So here’s to Redd never stopping.
I kind of feel like Redd’s cousin in the end, alerting the authorities they arrived a year late. Better late than never.

Our Call: STREAM IT. As Redd himself pauses to reflect after interacting with the audience at one point: “Yeah, we’re having fun here, for sure.” You best believe it.

Sean L. McCarthy works the comedy beat for his own digital newspaper, The Comic’s Comic; before that, for actual newspapers. Based in NYC but will travel anywhere for the scoop: Ice cream or news. He also tweets @thecomicscomic and podcasts half-hour episodes with comedians revealing origin stories: The Comic’s Comic Presents Last Things First.