While working at
NYCHA and the
Rockefeller Foundation as a speech writer, Cunningham started writing freelance theater and book reviews for
The Brooklyn Paper and
Nylon magazine. In 2014, Cunnigham entered and won a contest by
McSweeney's to create his own
column. In 2016, Cunningham began at
The New Yorker as a staff writer. He writes frequently about sports, including about the relationship between Lebron James and Kyrie Irving and his own
Knicks fandom. In 2019, Cunningham interviewed
Tracy Morgan shortly after he was in a near-fatal car accident. The piece was a finalist for the
National Magazine Award for Profile Writing. In June 2019, Cunningham and fellow staff writer Alexandra Schwartz became co-chief theater critics for
The New Yorker, succeeding
Hilton Als. Cunningham has been a member of the
New York Drama Critics' Circle. He also served as a judge for the 2022
PEN America Literary Awards. In 2024, Cunningham was a finalist for the
Pulitzer Prize for Criticism for his "formidable knowledge of the stage and the mechanics of performance along with canny observations on the human condition." His nominated works included reviews of
The Comeuppance, New York, New York versus
Good Night, Oscar, and Leslie Odom Jr.'s revival of
Purlie Victorious. He was again a finalist for the award in 2025, for "illuminating and personal reviews of work that appears on television, streaming services or social media, trenchant criticism that explores contemporary issues and society." His nominated works include reviews of
Jaleel White's memoir
Growing Up Urkel and
Nicole Kidman's
The Perfect Couple, as well as essays on
campaign advertising in the
2024 American presidential election and
Pat McAfee. In 2024
, an article in
The New York Times cited "Critics at Large" as an exemplar of the growing trend of successful "chat podcasts."
Great Expectations (2024) Cunningham published his debut novel on March 12, 2024. The semi-autobiographical narrative follows the protagonist David Hammond over the course of year, engaging in topics like "the social lexicon of intra-racial hierarchy," politics, Christianity,
class, and Hammond's sex life.
The Atlantic magazine reviewer Danielle Amir Jackson likewise concluded that it marked "a keen look back at the failed promise" of the early
Obama administration. Alternatively, Ruth Margalit argued in
The New York Review of Books that "one of the great pleasures of reading Cunningham is his behind-the-scenes account not of the Obama campaign [...] but of a critical mind being formed." Margalit compared the book more to
autofiction works by critics
Elif Batuman and
Ben Lerner than political chronicles like
The World As It Is by
Ben Rhodes. The novel was also a finalist for the
National Book Critics Circle award for "best first book" and was named to the longlist for the award for best fiction. == Personal life ==