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Legacy
In the decades following his death in 1964, O’Sullivan’s work has remained in both public and private art domains, particularly in Ireland. One of his most notable works, his portrait of the former President of Ireland, Éamon De Valera, is currently on display in Áras an Uachtaráin, the official residence and office of the Irish President.

Many of his portraits and sketches have since been sold at private auctions, with paintings like ‘The Man and Woman of the West’(1929) selling for €65,000 in 2008. In 2012, Adams Auctioneers of Dublin held a sale for their collection of O’Sullivan’s work. Less notable works sold for prices ranging between €2000-€10,000 and are still in demand in the current market.

Much of O’Sullivan’s work continues to be exhibited and held in archives at the National Gallery of Ireland in Dublin. O’Sullivan’s portraits of Jack Butler Yeats, James Larkin, William Butler Yeats, Maude Gonne, and many more revolutionary Irish figures of the early 20th century can be viewed on the online collection of the National Gallery website. A number of his works are also held in private archives in the National Folklore Collection in University College Dublin. His documentation of prominent Irish cultural, political and social figures of the early to mid-20th century makes up a significant part of his collection of works, and are still used as references in media today.

O’Sullivan can also be credited with assisting the preservation of the culture and heritage of the Great Blasket Island. His 1958 portrait of Peig Sayers, Irish historian and writer who was a resident of Na Blascaoid, is a part of the archive of Fondúireacht an Bhlascaoid, (English: The Blasket Foundation), dedicated to the conservation of the historical community and culture of the island, which is no longer inhabited. O’Sullivan's sketch portrait entitled ‘A Blasket Islander: Dunquinn (Irish: Dún Chaoin) (1932) depicts an elderly islander, most recently sold at auction for €3,800 in 2021, listed under Important Irish Art.

His legacy has been carried on his daughter, Terry Myler, who is a book illustrator.