Agitation for a link between The Rocks and Millers Point began early; the Sydney Gazette in 1803 lamented the lack of a short cut across the rocky peninsula. Before the cut was built, the only way that vehicles could get from the Sydney Cove to Darling Harbour was via a circuitous route along lower George Street, to Dawes Point and into Windmill Street. For pedestrians, there was no other way except along the steep alleyways and flights of crude steps.
The Argyle Cut was begun by 1843, with convict labour in chain gangs. Their overseer was a cruel man, Tim Lane, who used to declare to the labourers that 'by the help of God and the strong arm of the flogger, you'll get fifty before breakfast tomorrow!' Despite his efforts, the job proved beyond the crude tools of the convicts.
Transportation to NSW had ceased in 1840 after much agitation, and many of the residents were unsettled by the sight and sounds of convicts labouring in chains in full view. The Government abandoned the project when it was half completed.
The cut was eventually completed by Sydney Municipal Council, using explosives and council labour in 1859. The spoil was used to fill the mouth of the Tank Stream and to buttress the sea wall at Circular Quay.
Overhead bridges were built during the 1860s. There is an inscription identifying Charles Moore, Mayor (1867-8) from one of the Bridges now relocated to the south wall of the cut. With the building of new wharves at Walsh Bay and the laying out of Hickson Road the Cut lost much of its importance.
Later, as part of the building of the Bradfield Highway in the 1920s, the Princes Street Bridge was demolished, and the Argyle Cut was widened at the Princes Street end, and the Bradfield Highway was constructed overhead, completed in 1932.