The street itself largely consisted of Georgian and Victorian buildings. However the Easter Rising in 1916, when a small band of Irish republicans seized the General Post Office (GPO) and proclaimed an Irish republic, led to the street's bombardment by artillery. Much of the street was reduced to rubble. Many of those rebuilt where then destroyed again during the Irish Civil War (1922-1923). As a result, only one surviving georgian building exists on the street. The General Post Office itself was destroyed and has been rebuilt. Today, most of the buildings on the street date from the 1920s and 1930s. Apart from the GPO, the most famous buildings on the street include the Gresham Hotel, the Royal Dublin Hotel and Clerys department store. However poor planning controls in the 1970s allowed cheap shops and burger joints to open. After a couple of decades of neglect, the street has being undergoing a form of renaissance, with new street furnishings and the Spire of Dublin, the world's tallest scupture, which was erected in January 2003.
The street has a number of major monuments, including statues of late nineteenth century Irish political leader Charles Stewart Parnell, radical early twentieth century trades union leader Jim Larkin and Daniel O'Connell, who was the dominant force in Irish politics from the late 1820s until his death in 1847. One monument in particular, Nelson's Pillar, honouring British Admiral Horatio Nelson, dominated the streetscene, allowing visitors an unparalleled viewing platform to which people climb and see the city. The monument, which stood at the junctions of Henry Street, Talbot Street and Henry Street, was controversially blown up by Irish republicans in 1966. The controversial Spire of Dublin, has been erected on the site of the pillar.
Dubliners (who are famous for giving blunt nicknames to monuments) used to nickname the street 'the street of the Three Adulturers' because of the allegations of adultery made against the three principal figures on the street commemorated by statues; Parnell, Nelson and O'Connell. It was also noted humourously that the statue of Charles Stewart Parnell, on which appears his famous words "No man has a right to fix the boundary to the march of a nation. To say to his country 'thus far shall thou go and no further' are quoted, points to the Rotunda Hospital nearby, once Dublin's main maternity hospital, as though he was encouraging the Irish nation to outbreed its enemies.