10 of Chris Redd’s Best SNL Sketches

Photo: Rosalind O’Connor/NBCU Photo Bank/NBCUniversal via Getty Images

When Chris Redd joined the cast of Saturday Night Live in 2017, he hit the ground running like he was making up for lost time. A year prior, he’d auditioned unsuccessfully for the show’s 42nd season, and a number of press outlets had mistakenly reported he’d been cast on the show prematurely. By the time he officially joined the cast the following year, he was ready to prove he deserved to be there all along.

Over the course of five seasons, Redd became a reliable crutch the show leaned on every time a sketch called for a naïve dummy with a heart of gold, a swaggering character with limited self-awareness, any Black male celebrity Kenan Thompson was too old to play, a credible rapper, and, of course, Eric Adams. That’s all to say: His recently announced departure from the show will undoubtedly leave behind a huge void for one of its four new cast members to fill. To pay tribute to the impact Redd had on the show during his tenure, here is a roundup of sketches featuring some of his most unforgettable characters, impressions, and songs.

“E! New Line Up” (October 2017)

Redd never shied away from playing … let’s say maligned characters in pop culture. During his five years on the show he portrayed Kanye, Jussie Smollett, and Will Smith mid-slap. Okay, obviously the cold open where Redd-as-Kanye met with Trump (Alec Baldwin) and Jim Brown (Kenan Thompson) was a more bravura performance. But that sketch is deeply unpleasant for oh so many reasons. This early contribution to a pretaped sketch about Kanye’s reluctance to appear on Keeping Up With the Kardashians has zero Trump, zero Baldwin, and infinitely more hiding behind a decorative vase. —Bethy Squires

“Fresh Prince” (January 2018)

Redd does so much in this sketch with just body language and facial expressions, miming along to the cheerful-sounding parody of the Fresh Prince of Bel-Air theme song, while its narrative keeps heightening in outlandish ways. It’s one of many appearances he made on the show where it would be reasonable for a viewer to think he would have made a great silent-movie slapstick comedian had he simply been born in an earlier era. —Hershal Pandya

“Friendos” (May 2018)

Once Redd figured out that the word therapy fits in a Migos-style triplet meter, it was over for us hoes. As the years have gone by, Redd has become more outspoken about mental health and the benefits of therapy, but the notion of open communication being good for artists was there all the way back in 2018. —B.S.

“Trees” (October 2018)

“I like character work!” Redd shouts this in the middle of the anti-climate denial, pro-tree, pro–Al Gore rap “Trees,” and it really sums up his ethos. Doing a comedy rap? Good. Doing one in a wig and putting on an interesting voice? Better. In 2018, Redd told Vulture what the rap sketches meant to him: “It was my dream to rap. So when I make a rap song that works, and I wrote it, it feels like all of the things I worked for are coming to fruition. Everyone can see my idea, and I have more ownership over it.” What set Redd’s work apart from other comedic rappers was the commitment to trying different flows and integrating, as he says in the sketch, character work into the form. But it’s still him all the way down. —B.S.

“That’s the Game” (November 2019)

The archetype Redd seemed to return to most frequently on SNL was that of the overconfident dumb guy trying and failing to maintain his bravado in the face of a clear lack of understanding or ability. And for good reason: Redd is so good at playing these parts. He has this uncanny ability to speak like he’s in full control of a situation while his face betrays him, taking the shape of someone whose gears were visibly spinning before they got stuck. “That’s the Game,” a sketch in which he tries to hijack a drug empire but instantly realizes he doesn’t know how to run it, puts this particular talent on full display. His expression while attempting to load a gun by sticking a bullet directly in its barrel, before handing it to Mikey Day and saying “Here, screw this in for me,” should be a fixture on his acting reel forever. —H.P.

“Weekend Update: Soulja Boy on the Government Shutdown” (January 2019)

The remarkable part of this “Weekend Update” segment is that it shouldn’t work. At best, it was a flimsy excuse to shoehorn an impression of the week’s viral main character, Soulja Boy, into the show. (He’d recently participated in a widely memed interview on The Breakfast Club in which he balked at the idea of Drake’s rap supremacy by saying “Drake?!” in a funny voice.) That Redd was able to get so much mileage out of it regardless speaks volumes to the way in which he was always able to squeeze every ounce of laughs out of a sketch’s writing with his timing and performance. He’d contort his elastic face into looks of disbelief or misguided overcompensation and hit the right note on every line delivery. The incredulous way he walks away from the table and says “Obama?!” deserves to be clipped and put in a museum. —H.P.

“Bottom of Your Face” (October 2020)

Revisiting early pandemic comedy is rough. Remember when this was all new and (hopefully) temporary? Ha ha. But the hook of this song is so catchy you can’t dwell too much in the circumstances under which it was created. It’s a shame that Redd won’t be on hand to help with Megan Thee Stallion’s double billing in October, because the two work wonderfully together here. And then a little “No Sex in the Champagne Room”–style parody? What’s not to love?! —B.S.

“Weird Little Flute” (April 2021)

This one had flutists doing reaction videos on TikTok, so that’s fun! Redd always found comedy in the details of music, including the weird little flute that accompanies so many backing tracks. Once again integrating rap legends into the comedy (this time Kid Cudi, who is no stranger to jokes), this one is also prop comedy. The energy these boys bring to their weird little flutes is infectious. Everybody’s just so wriggly. —B.S.

“What’s Wrong With This Picture?” (April 2021)

The same night as “Weird Little Flute,” Redd brought an unfocused gaze and weird-ass delivery to recurring sketch “What’s Wrong With This Picture?” It has three uniquely dumb (and often perverted) individuals doing the absolute least on what should be the easiest game show in the world. Redd always brought it in any ensemble piece, giving even the teeniest of lines something special. The way he says “I like dogs!” in this one gets stuck in my head, as well as “Sure, I’ll be, I guess,” in 2017’s “New Wife.” Again, it’s the detail work we’ll miss. —B.S.

“ESPN’s First Take” (May 2022)

ESPN commentator Stephen A. Smith is a public figure who’s hard to heighten: His mannerisms are already so exaggerated and his speech is already so passionate. While impersonating him, Redd had no choice but to go supersonic. He gestured maniacally and screamed every line he delivered like he was about to burst a blood vessel in his eye. Talented mimics like Jamie Foxx and Jay Pharoah have attempted to impersonate Smith previously, but no one did it quite as hilariously as Redd, who realized the key to unlocking him wasn’t accuracy but to turn him into an apoplectic cartoon character biologically incapable of demonstrating even the tiniest modicum of chill. —H.P.

10 of Chris Redd’s Best SNL Sketches