The neighbourhood of Kings Cross (called “the Cross” by Sydneysiders) is perched on a high ridge overlooking the office buildings and sandstone cathedrals of Sydney’s central business district. Although its leafy streets, magnificent harbour views and easy access to both Circular Quay and the city’s famed eastern beaches make it a prime candidate for the title of Sydney’s most prestigious residential address, the reality is somewhat different.

Taking its name from the three-way intersection where William Street meets Darlinghurst Road and Victoria Street, the Cross occupies a few blocks clustered around a sleazy 600m-long spine of Darlinghurst Road that is full of strip clubs, peep shows and sex shops. Here, defeated-looking prostitutes and pumped-up bouncers stand in doorways, drug dealers skulk in alleyways, and drunks make slow and unsteady progressions along the pavement. It is a tawdry, depressing and often confronting scene during the day, but at night the stretch has a raffish and oddly alluring charm, underpinned by neon lights, pumping music and crowds of suburban revellers who gawk and giggle their way between a huge number of bars, pubs and clubs, many of which are open 24 hours.  

The genteel mansions that were built in the early 19th Century by the colony’s elite are long gone, demolished in the 1920s and ‘30s to make way for apartment buildings. These blocks, standing cheek-by-jowl on every street, make this neighbourhood the most densely populated area in Australia. The colourful and corrupt characters who work the Darlinghurst Road dens of iniquity do not faze the local residents; indeed, many believe that the seamy side of the Cross is its major asset, ensuring that the process of gentrification and associated real-estate speculation is kept at bay.

That is not to say that accommodation is cheap in the Cross or in the neighbouring enclaves of Potts Point and Elizabeth Bay. But the sheer number of apartments means that the likelihood of finding an affordable rental has been higher here than elsewhere in the city ever since the 1920s. As a result, artists, writers, actors, filmmakers and musicians have long called the Cross home. These self-styled bohemians argue passionately that the Cross is a state of mind rather than a mere postcode, a place where the louche and laconic charm of this convict-established city has always been evident, and where creativity can flourish.

Equally passionate about the area are the growing numbers of young professionals who are attracted by relatively affordable prices and seduced by the area’s convenient location and bohemian ambiance. Their advent (and disposable income) has triggered many changes to the local landscape.

Piccolo Bar Cafe, which opened in the 1940s and swiftly developed a reputation as a hangout for local jazz musicians, still attracts a loyal crowd and has provided a blueprint for the growing number of new cafes, bars and restaurants opening in the streets and laneways off Darlinghurst Road. Room 10 (10 Llankelly Place; 0425-810-174), for example, has an arty decor, alternative soundtrack and staff who wait tables to fund their artistic endeavours; a long and proud tradition here in the Cross.

In the past, many of the suburb’s restaurants were hotbeds of petty crime (the oldest and best-loved Chinese restaurant – now, alas, closed – hit the local headlines in 1950 when its manager Charlie Fong was charged with receiving stolen gold rings), but these days food and drink are the only commodities being traded on the restaurant floor. Popular options include Ms G’s, which has been serving up Japanese, Chinese and Southeast Asian dishes and a top-notch selection of beer and sake to crowds of raucous regulars since opening in late 2010; and The Apollo, which opened in February 2012 and offers modern Australian takes on Greek classics, such as wild weed pie, fried saganaki cheese and slow-cooked lamb with lemon and yoghurt.

Bars and pubs have thrived in the area since 1916, when ”six o’clock trading“ was introduced by the New South Wales state government. This local version of Prohibition forced all licensed venues to close at 6 pm, and sly-grog shops proliferated in the Cross as a result. During World War II, late-night clubs opened to entertain American servicemen on leave, a tradition that grew during the Vietnam War. In 1967, US Air Force veteran Bernie Houghton, who ran covert air operations for the CIA in Vietnam, opened the infamous Bourbon & Beefsteak bar-restaurant, a favourite haunt of both American GIs and the city’s criminal classes. Now known as The Bourbon, this local watering hole reopened in March 2013 after a major renovation. Some locals are lamenting the loss of its rough-as-guts decor and ambiance, while others are relieved that its bar-room brawls, sticky floors and ever-present aroma of stale beer are things of the past. Instead, patrons can enjoy live music and New Orleans-style cuisine, from jumbo shrimp to jambalaya.

The resident boho crowd may be wary about the slick renovations of local institutions, but they have welcomed recent initiatives at the Kings X Hotel with open arms. Since mid-2011, this six-storey building on the corner of William Street has hosted FBi Social, a venue run by the alternative radio station of the same name (94.5FM). Live music by up-and-coming local bands and one-off art and performance events are staged from Thursday to Saturday; on other nights of the week the hotel’s rooftop bar is a popular draw. Patrons include locals, backpackers staying in nearby hostels and music fans from across the city.

It seems unlikely that the tawdry scene along Darlinghurst Road will change any time in the near future, but the rest of the Cross is benefitting from an influx of residents who are firmly committed to retaining, promoting and building on the neighbourhood’s rich bohemian heritage. For a fascinating guide to the area’s past, follow the City of Sydney’s heritage walking tour. And for a glimpse into its future, wander north of the famous red-and-white “Enjoy Coca-Cola” billboard and into the many streets and laneways off Darlinghurst Road, where the true heartland of this fascinating neighbourhood lies.