Early life
Longfellow was born in Phoenix and grew up there. His mother, who is an attorney, and father later divorced. His stand-up comedy includes references to the fact that both of his parents remarried, resulting in his having stepparents.
During his first year at Arizona State University in Tempe, where he earned a BA in English literature, Longfellow started performing stand-up comedy.
Career
After his 2016 college graduation, he moved to Los Angeles and began performing in comedy clubs across the country, as well as at the Netflix Is A Joke festival during its "Netflix Introducing..." showcase. He has also appeared on Conan and Bring the Funny, a reality competition series on NBC co-hosted by his future SNL colleague, Kenan Thompson.
In 2022, it was announced that Longfellow would be joining the cast of Saturday Night Live (SNL) as a featured player for its 48th season. On October 1, 2022, he made his SNL debut as a new featured cast member. In his first episode, he appeared on Weekend Update talking about relatives who are anti-vaccination and actress Sydney Sweeney’s Trump-supporting family members.
On August 28, 2025, it was reported that Longfellow had left the show, after three seasons of being a cast member. His final episode aired on May 17, 2025, with host Scarlett Johansson.
In 2026 he was in an off-Broadway play called Broken Snow at Theater 71 with Tony Danza.
