In 2003, Gribbon moved to New York City to pursue a career in art, where she briefly worked as a cocktail waitress and a color technician for artist Jeff Koons.[3][5] In 2006, she was commissioned to paint copies of three portraits for Sofia Coppola's film Marie Antoinette.[3][7] From October to November that year, her debut solo show Empty Paintings and Imaginary Sculptures was exhibited at the Sarah Bowen Gallery in Williamsburg, Brooklyn.[3][8]
In 2010, Gribbon and writer Julian Tepper founded the Oracle Club, a literary salon and artist workspace in Long Island City.[9][10][11] While running the salon, Gribbon continued painting portraits of her friends and family and exhibiting work. When the Oracle Club closed in 2016 due to rising rent, she began studying at Hunter College, graduating in 2019 with her Master of Fine Arts.[6] In 2018, she was commissioned to create a portrait of Elsie Fisher for the film poster of Bo Burnham's Eighth Grade.[12]
After graduating, Gribbon's work largely focused on the exploration of queer identity and sensuality, and she has received positive reviews for her intimate depictions of women and gender in various solo shows.[13][14][15] She has cited artists like Édouard Manet, Jacques Rivette, Mary Cassatt, Karen Kilmnik, and Jean-Honoré Fragonard as inspirations for her work.[1][16]
Gribbon directed the music video for Torres' "Too Big for the Glory Hole" in 2020.[3] She also painted the cover art for Torres's albums Silver Tongue (2020) and Thirstier (2021).[17][18] In 2021, her paintings appeared in a two-person show at Sim Smith Gallery, alongside the films of Agnès Varda, who Gribbon has cited as an inspiration for her work.[1][19][20]
Her work has also been featured in group exhibitions at the Museum of Modern Art, Warsaw,[21][22] the Museum of Contemporary Art Jacksonville,[7] the Modern Art Museum of Fort Worth,[23] and the Leslie-Lohman Museum of Art.[24] At the Frick Collection in 2022, Gribbon's painting What Am I Doing Here? I Should Ask You the Same appeared in juxtaposition to Hans Holbein the Younger's portrait of Thomas Cromwell, occupying the space typically reserved for Holbein's portrait of Thomas More.[3] That October, her solo show Mirages opened at the Collezione Maramotti.[3] From September to October 2024, the David Kordansky Gallery exhibited her show Like Looking in a Mirror.[7]
In her introduction for the 2023–24 exhibition Jenna Gribbon: The Honeymoon Show, at the Lévy Gorvy Dayan Gallery,[13] curator Alison M. Gingeras wrote:
Her paintings demonstrate how a muse can also be a full-fledged subject, as opposed to a one-dimensional object of desire, and that looking as well as depicting can be an ethical, equitable exchange, and that desire or love can be conjured reciprocally without recourse to objectification, an ethos similarly articulated in [Celia] Paul's Self-Portrait.[2]