[10] In the 1860s–1920s, Gloucester Street was the northern end of the notorious Monto red-light district, where thousands of prostitutes lived and worked.

[13] The Gloucester Diamond is mentioned in Pete St. John's song "Johnny McGory", about a First World War veteran who returns to Dublin having lost a leg.

[14] An IRA safe house was located at 36 Gloucester Street Lower during the Irish War of Independence; Conor Clune, Dick McKee and Sean Fitzpatrick were arrested there on 21 November 1920, the day before Bloody Sunday.

[11][15] In 1933 the street was renamed for Seán Mac Diarmada (McDermott, 1883–1916), an executed leader of the Easter Rising.

[28] Today, the Irish headquarters of the Society of Saint Vincent de Paul are located on Seán McDermott Street as well as a Simon Community hostel which is housed in the former carpenters' asylum, an impressive regency style former guildhall at number 35.