After several years performing stand-up comedy, Redd was hired to join the cast of the NBC sketch comedy series Saturday Night Live ahead of the show's 43rd season in 2017, making his debut alongside Heidi Gardner and Luke Null, and serving as a cast member for five seasons until 2022.
For his work on the show, he won a Primetime Emmy Award for Outstanding Original Music and Lyrics in 2018 for co-writing the SNL song "Come Back Barack".
[7] After a previous unsuccessful audition for Saturday Night Live,[14] it was announced in September 2017 that Redd had joined the show's cast as a featured player for season 43, alongside fellow newcomers Heidi Gardner and Luke Null.
[23] Redd appeared in the 2023 film Spinning Gold as Frankie Crocker, a disc jockey for the first black music radio station in New York.
[27] In June 2020, Redd and fellow The Second City alumna Lisa Beasley raised over $360,000 on GoFundMe to cover the medical costs of racial justice protesters who had contracted COVID-19.