To get noticed in the comedy biz, you have to make noise. Lots of it. That’s at least what Chris Redd says. And you have to believe a guy who worked and joked so hard that he went from Second City student to “Saturday Night Live” cast member in a few short years — and just won an Emmy, on top of it.
The comedian, 34, was born in St. Louis and grew up in Naperville where he “actually didn’t spend much time.” Instead, you could catch him recording rap at Gremlen Studios in Aurora or driving back and forth to Chicago on a near-daily basis to soak up the improv and standup scene, particularly at Second City or iO.
“I grew up on ‘In Living Color’ and ‘Mad TV’ and knew that was what I loved but I’d have to be a super-hard worker to get there,” says Redd. “As a black actor you can feel like a lot of improv isn’t really catering to you, and a lot of people get turned off. I saw that and fought through it. I thought, ‘I gotta push and see what this could all be about.’ ”
Redd’s hustle was in part inspired by his dad, who for 16 years worked as a loan officer on Chicago’s South Side. He spent hours driving to and from his job every day. And Redd knew that if his dad could put in the miles, so could he. So, heading into the city became Redd’s thing. When he got there he channeled his fierce energy into performing — whenever and wherever possible.
That ready-for-anything fuel came in part from the fact that Redd wasn’t sleeping much. In fact, he still calls himself somewhat of an insomniac. “You can get a lot done at night,” he says, laughing.
The twilight hours were sometimes spent rehearsing for his auditions for “SNL,” which paid off in 2017 when Redd got cast; it was at the same time he was working on Netflix’s “Disjointed.”
But being on “SNL” wasn’t always Redd’s goal. “I’m a comedy rebel,” he explains. “People were always telling me what I had to do to get on the show and I was like ‘nah.’ I wanted to take the pressure off. But when the opportunity came, I knew if I didn’t get it, I’d be devastated.”
In his first year on “SNL” Redd cowrote a sketch with Will Stephen and Kenan Thompson, which featured him, Thompson, and Chance the Rapper, with production by Eli Brueggemann. Called “Come Back Barack,” it’s a parody of a B-joint music video, and laments the end of the former president’s term. It landed the team an Emmy Award for Outstanding Original Music and Lyrics in 2018. Now back for his second season, Redd continues to play memorable characters. Among those is “Darius Trump,” the son of the president, reimagined from a diverse perspective, in a hilarious send-up called “Them Trumps.”
Still, all the “SNL” success wouldn’t be possible without the groundwork he laid in Chicago — even back in middle school. “I would write raps about kids’ stuff … like beating up Barney when I didn’t want to clean my room,” says Redd. “And I would get in lunchroom battles. I was always rapping and rhyming.”
Redd adds that, as a preteen, he was an introvert, and rapping gave him an identity. It was through rap that he began writing jokes to fit a rhythm. Pushed by friends to try comedy, he started with standup in 2009. “I was trying to figure out a life without rap,” he says. “When I got to Second City, I fell in love with it and told myself I wanted to take this as far as I possibly could.”
True to his self-promise, Redd was soon found camped out on the fourth floor of the theater building, writing sketches and practicing with friends. With all the troupes he was in, including buzzy ones like the Freshmen, he turned out enough material to do new shows every two weeks. On the side, Redd hit the standup circuit and took acting and improv classes around town at places like Annoyance Theater and iO.
Redd’s raw and topical humor struck a chord with many. “I like to troll and I like to roast,” he says. It’s true he doesn’t hold back on Twitter (@reddsaidit), where he skewers everything from the Trump administration to Tabasco sauce. Same goes for his just-released album, “But Here We Are,” which splices together some of his best live standup bits.
Second City director of alumni relations Beth Kligerman, who’s still friends with Redd, describes him as a “unique bird, and one of very few who dabble in so many things and do it successfully.” She explains, “Whether he had a show or was understudying, he’d use the theater as headquarters and would hunker down and work for hours straight. He was always ready to go in and try characters out of his willingness to learn.”
Down for anything describes Redd at this very moment. Whenever he’s in town, he blazes through the city to perform with old friends at their classic haunts. It’s obvious his heart for Second City and those connections aren’t fading anytime soon. “That place is a huge character in my life,” he says. “I used rap as a way to not be vulnerable. But through comedy, I found my vulnerability. I was failing a lot [onstage]. But I was winning, too. And that helped me find who I really am.”
“This was the first theater ever to give me a solo show. It’s where I also did first improv jams.” 3209 N. Halsted theplaygroundtheater.com
“This is where you learn to be different and embrace darkness. [Cofounder] Mick Napier taught me patience and how to embrace the weird.” 851 W. Belmont theannoyance.com
Jokes and Notes
“Here I found my voice in standup and learned how to translate it to sketch in front of an all-black audience.” formerly at 47th & King
The Second City
“My introduction to improv how to collaborate with people, building on ideas and really learning to write comedy.” 1616 N. Wells secondcity.com
“The place was full of comedians you should know—if you were in the city, you’d want to hit it do to standup, and you’d want to rock the show.” 622 N. Fairbanks timothyotooles.com
“They taught me how to really improvise, build a scene, and play a game. How to play subtly and how to lose.” 1501 N. Kingsbury iocomedy.com
AT THE SHOOT
“Saturday Night Live” ’s Chris Redd returned to his old stomping ground, The Second City, where he had our photo crew laughing at “hello.” The theater has changed a lot since Redd studied and performed there from 2012 to 2014, but that didn’t stop him from seeking out old pals and looking for his favorite couch where he used to write (and sleep!) for hours.
Left Suede Denim Jacket Jermaine IG by Grevyi Chicago, Pants Givenchy, Sneakers Puma Clyde
On the cover Snapback Lids, Denim Shirt Off-White, Jeans Purple Denim, Hoodie Saint Laurent, Air Jordan 2 Retro BHM Station 23
Photographer Maria Ponce
Wardrobe styling Corey D. Williams
Barber Ron Sherrod
Groomer Lynee Ruiz