Craig Calderwood was born in 1987 in Bakersville, CA and raised in California's San Joaquin Valley. From a young age, Calderwood found drawing to be an outlet and tool for self-expression, which later led to their interest in pursuing art. After taking classes at Fresno City College, they relocated to San Francisco, CA, in 2011, where they currently lives and works.

Calderwood’s multivalent practice ranges from drawings and paintings to sculptures, often featuring intricate patterns and utilizing “lowbrow” materials. Their work is heavily autobiographical, reflecting on their childhood experiences and identity as a queer and trans individual. To address gender fluidity, as well as ideas about desire, biodiversity, and otherness, they portray androgynous figures and body parts that are in some way unfamiliar. This is amplified by the extensive and highly detailed patterning that conceals any visible secondary sex characteristics, creating what Calderwood describes as “genderlessness.” Calderwood’s personal vernacular of symbols and patterns derives from the private languages used by queer and trans communities for decades, and is informed by historical research, personal narratives and pop-cultural moments. Materiality is also a significant aspect of Calderwood's work both conceptually and autobiographically: their father upholstered furniture professionally and the importance of this personal connection to textiles is evident. When starting paintings – which Calderwood also refers to as tapestries – they begin with a patchwork of upholstery fabrics, the tactile surface becoming an element of the work akin to the patterning. Textiles are also incorporated into their sculptures along with fabric paint, polymer clay, and pipe cleaners in a commentary on the societal tendency to view these materials as craft supplies. By subverting the intended use of their materials, Calderwood blurs the line between the binary of art and craft, much as they blur distinctions of sex and identity.

Calderwood has exhibited their work internationally and has been the recipient of numerous awards and residencies. Calderwood was the Eureka Fellowship Grantee in 2022, Art+Process+Ideas (API) artist in residence at Mills College, Oakland in 2020 and 2022, the SFMOMA SECA award Finalist in 2019, and is currently Artist-in-Residence at Recology, San Francisco. Calderwood was awarded three Individual Artist Commission grants from the San Francisco Arts Commission and in 2021 was selected to design and create artwork for the three-story atrium of the Harvey Milk Terminal at the San Francisco International Airport, set to be unveiled in 2024.