Chowdhury was born in Ulpur, East Bengal (now Bangladesh) into a Zamindari family, and graduated from the Government College of Art and Craft, Kolkata, in 1956. He later studied under the sculptors Prodosh Dasgupta and Sankho Chaudhuri at the M.S. University, Baroda. Between 1960 and 1962, he served as the Head of the Department of Sculpture at the Indian Art College, Kolkata.

Influenced by Indian sculptors like Prodosh Dasgupta as well as Western greats like Rodin, Roy Chowdhury found his inspiration in Hindustani classical music. His works, while pictorial are also largely abstract in their style – perhaps a result of his travels to the Academia de Belle Arti, Florence, in 1962, where he met Giacometti and Henry Moore in person, who along with Sankho Chaudhuri had an undeniable impact on his style. His sculptures feature a unique mix of the academic realism of the East and the more innovative cubism and abstraction of the West.

Roy Chowdhury has won several awards including the Gagan-Abani Puraskar from Visva Bharati University, Santiniketan, in 2004, and the Abanindra Puraskar from the Government of West Bengal in 2005.