He was hired to join the cast of the NBC sketch comedy series Saturday Night Live as a featured player for its 48th season in 2022, making his debut alongside Marcello Hernandez, Molly Kearney, and Devon Walker.

His mother and attorney father later divorced; Longfellow's comedy includes references to the fact that both his parents have remarried often, resulting in a collection of stepparents.

During his first year at Arizona State University, where he earned a BA in English literature, Longfellow started performing stand-up comedy.

[4] He has also appeared on Conan and the NBC reality competition series Bring the Funny, co-hosted by his future SNL colleague, Kenan Thompson.

In his first episode, he appeared on Weekend Update to discuss anti-vaccination relatives and actress Sydney Sweeney’s Trump-supporting family members.