Greg Bailey was born in 1986 in Warsop, Trelawny. He earned a BFA from the Edna Manley College of the Visual and Performing Arts in 2010, where he now serves as a lecturer, and an MFA from Washington University in St. Louis, Sam Fox School of Design and Visual Arts, in 2019. Bailey's practice focuses primarily on painting and drawing, serving as an ongoing exploration of post-colonial spaces such as Jamaica and the wider Caribbean. His work examines the persistent colonial residue within contemporary Caribbean environments, which fosters a complex and often confusing sense of self and space. This condition forms the core of his engagement with issues of race, gender, identity, and various socio-political complexities. These cultural phenomena function as both visual and conceptual elements within the narrative framework of his artistic practice.

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Bailey's Jamaican exhibitions include Post-Colonial Paraphernalia, his debut solo exhibition; Young Talent 2015; the 2012 National Biennial; the Jamaica Biennial (2014 and 2017); and the Kingston Biennial 2022, all held at the National Gallery of Jamaica. He has also participated in the "...And I Resumed the Struggle" exhibition series at the Olympia Art Gallery.

Beyond Jamaica, Bailey has exhibited in London, England; the United States; and Stuttgart, Germany. His accolades include the People’s Choice Award at the Due West 2020 exhibition, National Gallery West, Montego Bay; the Danforth and CHASE Fund Scholarships; and the Dawn Scott Memorial Award. Bailey is also the author of Future Relics: Monumentalizing Afro-Caribbean Identity (2019).