The Bailey pub, formerly The Maltings, had always been a hub of literary and political activity. Prior to John Ryan’s acquiring it, it had welcomed international artists such as Evelyn Waugh, John Betjeman, and Charles Chaplin, as well as being popular with local figures like Oliver St. John Gogarty, Pádraig Colum and Thomas Kettle. Charles Stuart Parnell, leader of the Irish Parliamentary Party, frequently met with his supports here, and Arthur Griffith, founder of Sinn Féin, spent his evenings in the pub after long days at the nearby National Library on Kildare Street.
Under John Ryan’s direction the pub again became fertile ground for artists and writers in the 1950s and 60s. Ryan maintained close relationships with all of the significant figures of this period, such as Patrick Kavanagh, Samuel Beckett, Brendan Behan, Brian O’Nolan and J. P. Donleavy, many of whom he also supported financially.
It was in this context that Bloomsday, a celebration of Joyce’s Ulysses, first emerged. Ryan arranged for two horse drawn carriages to take participants from the Martello Tower in Sandycove, where the novel begins, across the city, following in the footsteps of Leopold Bloom and Stephen Daedalus. Present were Kavanagh and O’Nolan, as well as the architect Michael Scott, critic Anthony Cronin and Joyce’s cousin Tom Joyce. As they progressed through their journey the cortege stopped frequently at pubs and by the time they reached the city centre, exhausted and inebriated, they abandoned the expedition for welcoming warmth of The Bailey.