The Untold Truth Of Chris Redd

Chris Redd has emerged as one of the funniest, most interesting, and singular comedians to break big on “Saturday Night Live” in the past decade. Since arriving on the storied late-night sketch show in 2017, fresh off his dynamic and attention-getting role as rapper Hunter the Hungry in the instant comedy cult classic “Popstar: Never Stop Never Stopping,” Redd brought his unique style and energy to “SNL,” imitating figures like Cory Booker, Nick Cannon, Jordan Peele, and Kanye West. His most prominent contribution to “SNL,” however: conceiving and performing in funny and satirically withering pre-taped comic music videos, including the lamenting “Come Back, Barack,” consent-oriented “Permission,” and hip-hop-skewering “Weird Little Flute.” 

In 2021, Redd started pulling double-duty, co-starring on NBC’s hit sitcom “Kenan” with his “SNL” colleague Kenan Thompson, and that’s not even counting his stand-up gigs and movie work. Here’s a look into the background and influences surrounding one of the biggest and still rising stars in modern comedy, Chris Redd.

Chris Redd initially wanted to be a rapper

Chris Redd is a comedian first and foremost, while rap and hip-hop loom large in his work. His first movie role was as the rapper Hunter the Hungry in “Popstar: Never Stop Never Stopping,” and on SNL,” he often stars in funny rap spoofs, like a twisted take on “The Fresh Prince of Bel-Air” theme song and the Migos send-up “Friendos.” Before he started performing stand-up and pursuing acting, Redd aspired to be a rapper — a serious one.

Redd was born in St. Louis but moved to the Chicago suburb of Naperville at age eight, then spent his teen years hanging out with gang members in order to “try to be down,” he told the Chicago Sun-Times. “I wanted to prove myself to my street friends that I had what it [took] to be out there and that I could build my life and then rap about it cause that’s the kind of rappers I love,” Redd told Ebony. After determining that his friends’ lifestyle wasn’t for him per se, he got interested in hip-hop for tangential reasons. “Rap helped me find my swagger,” he said. “It also helped me get rid of my stutter,” the comedian explained to the Chicago Sun-Times.

Chris Redd came late to comedy, but he went at it intensely

While Chris Redd’s earliest serious career ambitions were rap-minded, he secretly harbored a deep love and appreciation for comedy. He grew up listening to his father’s Richard Pryor stand-up albums and devoured comedy specials whenever they would air, but it took Redd a while to realize that doing comedy was a viable artistic path. “It wasn’t until I was 22 that I even thought it could actually be a career,” Redd told Bonobos. “I always looked at comedy as this other thing I can just kind of do — as a personality thing that enhanced my rap persona.” It wasn’t until he took an improv comedy class, watching adults acting as trees, that it clicked. “I didn’t feel like, ‘This is stupid as hell.’ I was like, ‘Damn! This is kind of cool!'”

Per Ebony, Redd rose through the ranks through classes at comedy clubs, learning and honing the skills to make it as a professional funny person. He also credits his success to enacting the advice of a stranger. He once saw a young man driving a nice car and asked him how he got so wealthy so early. “He was like, ‘Yo man, honestly, I just cut out anything that wasn’t about the work for three years, and I just went hard for three years. From sun up to sun down.'” Redd took the same three-year approach to comedy, “extending the years” until it worked out (via Bonobos).

Chris Redd once bombed in front of everyone he knew

Nowadays, Chris Redd is adept and assured at all types of comedy — comic acting, sketch work, stand-up — but it wasn’t always the case. Around 2009, Redd entered a high-profile comedy competition in Chicago, an event made all the more significant thanks to the presence of celebrity judge Lil Rel Howery. It hadn’t been long since Redd had abandoned his rap ambitions in favor of stand-up, to the confusion of family and friends. “I sent a mass email like: ‘This is the grand opening of my comedy!’ Because everybody was doubting me,” he told the Chicago Tribune. Many recipients attended. “Everybody was there. My old pastors came. Their family. My family. Teachers … Just random people from my life and my past,” Redd said.

The show didn’t go so well. “I started by mumbling some things because I got real nervous and I was making some quips and they were not working,” Redd recalled, which he then followed with a bit about how he had on a new shirt that he’d return to the store if he didn’t win the competition. “I don’t know why, but I thought it was hilarious.” Then, after a five-minute routine that “felt like an hour and a half,” the judges told him he did a terrible job and numerous members of Redd’s inner circle told him he’d made a “bad decision” to go into comedy.

Chris Redd's Popstar audition was an arduous process

Chris Redd’s breakout performance came in the 2016 comedy “Popstar: Never Stop Never Stopping.” Written and directed by and starring the members of the Lonely Island troupe, it’s a mockumentary about a musician named Conner4Real (Andy Samberg) who reconnects with his childhood friends and cohorts in the pop-rap group The Style Boyz, after being completely overshadowed on a concert tour by an intense, inscrutable, and unhinged hip-hop star named Hunter the Hungry. 

Hunter the Hungry was Redd’s role, one that required both comedic and rap skills. To check the comedy, producers had Redd audition with what would become his “favorite” scene in the movie, where Hunter won’t admit to publicly pranking Conner4Real, making him appear to have no genitals during a big concert. To check the musical element, the filmmakers set Redd loose, telling him to freestyle rap. “So I rapped for 20 solid minutes straight,” he told Vulture. “I don’t know if it was funny, but I rapped a lot.” Redd got a callback to read for a few more scenes, and again, producers wanted to see his musical skills. “‘Yo, we wanna see some rap again,'” Redd recalled them saying, “‘but like way less, bro.'”

Chris Redd's potential big breaks didn't work out

The two projects that shot Chris Redd into the upper echelon of mainstream comedy, “Popstar: Never Stop Never Stopping” and “Saturday Night Live,” arrived in rapid succession in 2016 and 2017, respectively. But nobody ever becomes famous (or skilled enough to get cast in big movies and legendary sketch comedy institutions) overnight or in a vacuum. 

Before “Popstar” and “SNL,” Redd racked up lots of credits, notably playing sound engineer Roger in early episodes of “Empire” and guest-starring on an episode of “Chicago P.D.” The actor also had a knack for landing gigs on promising comedy shows that didn’t last very long. Two years after appearing on five episodes of the short-lived 2012 show “Last Laff,” Redd was selected for the cast of an untitled NBC sketch series (with future “SNL” co-star Alex Moffat) that didn’t make it to a full series.

 In 2015, Redd played Steven on “Family Fortune,” a North Carolina-set TV comedy starring and based on the comedy of stand-up Fortune Feimster. A potentially long-lasting gig on “Disjointed,” a Netflix sitcom about a marijuana dispensary co-created by “Two and a Half Men” mastermind Chuck Lorre, abruptly ended after one season, but by that time, Redd had found a home at “SNL.”

Chris Redd's circuitous route to Saturday Night Live

After virtually stealing the 2016 movie “Popstar: Never Stop Stopping” out from under its ostensible star, former “Saturday Night Live” standout Andy Samberg, Chris Redd seemingly landed a spot at his co-star and on-screen rival’s former stomping grounds. 

Multiple media outlets, among them The Comic’s Comic, reported from reliable and trustworthy sources that Redd had aced his August 2016 “SNL” audition and that he would be joining the historic sketch comedy series for its 42nd season that fall. However, when the media team of “SNL” actually and officially announced the new cast additions in September 2016, Redd wasn’t on the list of hires alongside Melissa Villasenor and Alex Moffat. Redd ultimately would join “Saturday Night Live,” but not until the fall of 2017, a year after his initial audition. That he even got on at all still slightly mystified Redd years later. On “Conan” in 2018, he said that his tryout consisted largely of jokes “about crackheads.”

Chris Redd won a rare Emmy Award

In September 2020, according to Billboard, “Saturday Night Live” won its 80th Emmy Award, more than any other TV show ever. Most of those trophies for the series, airing since 1975, have come for technical achievements or were given to guest hosts. Rarely does a regular cast member on the show take home the most coveted prize in television. Out of the dozens of cast members over the decades, only Kate McKinnon, Chevy Chase, Gilda Radner, and Dana Carvey have been singled out by Emmy voters for their acting work. 

In 2018, Redd took home an Emmy Award, along with “SNL” writers Will Stephen and Eli Brueggemann and co-star Kenan Thompson, for Outstanding Original Music and Lyrics. Redd’s prize came for “Come Back, Barack,” a Boyz II Men-style slow jam about missing former president Barack Obama during the Trump era, which he performed with Thompson and “SNL” musical guest Chance the Rapper. With his win, Redd won “SNL” its first Emmy win in the Original Song category since 2011, and he also became only the second “SNL” cast member to win an individual award in their first season on the show (the other original cast member was Chase, back in 1976).

Chris Redd does two shows at the same time

Most actors dream of landing one high-profile gig, like a regular role on a network TV series. As of 2021, Chris Redd was lucky and rare in that he had two major performing jobs at the same time. In addition to his ongoing work as a repertory player on “Saturday Night Live,” he co-starred on the NBC sitcom “Kenan” as the easygoing but kind of sketchy Gary Williams, brother of the titular TV morning show host character portrayed by his “SNL” castmate Kenan Thompson. Helping to prepare a 90-minute sketch comedy show each week is hard work, and Redd does that while also filming a single-camera, cinematic-style sitcom simultaneously. Adding to the workload of two full-time jobs, according to Vanity Fair, is that the shows shoot on opposite sides of the United States: “SNL” in New York, and “Kenan” in Los Angeles.

Notably, Redd agreed to do with “Kenan” without hesitation. During the week Eddie Murphy hosted “SNL” in 2019, which Redd called “the best week” of his life, “SNL” and “Kenan” producer Lorne Michaels called the actor to his office and asked Redd to play Thompson’s brother. He immediately agreed. “I didn’t even read the script, nothing. It didn’t matter — it was Kenan,” Redd said.

Chris Redd raised a lot of money for COVID-19 victims

In the midst of the COVID-19 pandemic in the spring of 2020, during which many American cities and states issued stay-at-home orders and businesses closed down to limit the spread of the disease, a spate of police killings of African-Americans prompted large-scale protests in favor of the Black Lives Matter movement and calling for an end to police brutality. From a moral standpoint, thousands upon thousands of people felt they had no choice but to take to the streets to speak out against cruelty and injustice, even if joining the assemblies increased their risk of exposure to COVID-19.

“Saturday Night Live” star Chris Redd started a charitable drive to specifically benefit people who took to the streets to advance a cause and got sick in the process. “I’m working on a relief fund for front line protestors who may contract COVID-19 over the next couple of weeks due to body to body contact,” Redd tweeted on June 1, 2020. “I would hate for my people fighting for justice struggle later because of it.” The next day, Redd had set up a GoFundMe for the COVID-19 Protest Relief Fund, which in two days raised a quarter of a million dollars for its beneficiaries, according to the Chicago Tribune. By the end of the month, the total raised neared $400,000.

Chris Redd is on a mission to get racism out of comedy

In any of its forms, comedy is often supposed to offer a call-out and critique of society’s ills. Prominent comedy people like Chris Redd believe that there’s no place for racism and sexual misconduct in the comic organizations that hold up that critical mirror to society. At the “Top 10 Comics to Watch” showcase at 2018’s Just for Laughs festival, comedian Darren Knight — best known for his “Southern Momma” character in online videos, per Vulture — was virtually booed off the stage. After appearing on a panel and dismissing the need to eliminate racism from comedy, Knight hit the stage for an ill-received set. When he was done, he called comedian Dulcé Sloan, who is Black, “Precious” (as in the flick, “Precious”). “He had been verbally attacking me all day,” Sloan said. After the show, host Redd confronted Knight backstage, telling him that “real comics write real jokes.”

In June 2020, Andrew Alexander, the CEO and co-owner of Second City, the comedic theater and improv organization that’s produced many TV and movie stars — including Redd — resigned after admitting that he didn’t do much to foster an “anti-racist environment” at the company, per Deadline. That prompted 19 Black alumni of Second City, including Redd, to publicly call for an investigation into the theater to root out racism and improper conduct.

Chris Redd pulls from real life on Saturday Night Live

Chris Redd joined the cast of Saturday Night Live in the fall of 2017 as a featured player. He also sometimes helps write his own material, particularly his many humorous hip-hop videos. One of Redd’s most memorable — and culturally-relevant videos — came in the show’s 46th season premiere, and featured the episode’s musical guest, rapper Megan Thee Stallion. 

“Bottom of Your Face” is a sexy, flirty song in which Redd, in character as a rapper alongside castmates Kenan Thompson and Pete Davidson, implores some young women to take off their COVID-19 infection-preventing masks so they can get a look at their entire visages. They refuse, what with the pandemic and all. While the musical sketch takes an amusing if heightened and absurd look at trying to date while also avoiding the coronavirus, it’s also at least loosely based on real events. “So many things have happened in this pandemic that is funny to us. I was also dating somebody and hadn’t seen the bottom of her face. I had only seen her with a mask,” Redd told Complex. “There’s always something to find to flip things on its head.”

Remaining vigilant for comedy affects Redd’s writing process, which eschews the traditional SNL sketch creation dynamic. According to The Hustle, most sketches are written for a particular episode, and a few days before. Redd will develop his material, the more complex musical numbers specifically, in the off-season (via Chicago Tribune).

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