But with a recent state government crackdown on crime, violence and rowdy behaviour, the hedonism of Kings Cross and its dark underworld has been muted.
The once-seedy area where the sex business flourished has given way to trendy bars and restaurants. Neon signs have been replaced by plastic banners which scream "Keep Sydney Open" amid the city's controversial lockout laws. Former late night pubs now have curfews which inadvertently send revellers elsewhere. Some of the venues have closed permanently.
But there's something missing from the old prostitution haunt that isn't a result of changes to the laws. The street walkers Kings Cross was infamous for in its heyday have largely vanished from the area, although brothels and escort services remain rampant.
According to several sex workers who spoke with news.com.au, technologies including the internet and mobile phones have diminished the need for many of them to take to the streets in the first place. Instead, advertisements for sexual services flourish on websites.
While prostitution may be less visible it is no less prevalent.
One sex worker, who spoke to news.com.au on the condition of anonymity, said she doesn't need to "hustle on the streets" any more because she advertises her services online and arranges to meet clients over the phone or via the internet instead.
Another Sydney sex worker, who didn't want to be named, told news.com.au the internet was "driving prostitutes off the streets".
"There used to be about 25 of us working the main strip (in Kings Cross) on any given weekend whereas now it's down to a handful," she said.
"It's a lot safer than it used to be but there are risks with everything and you've still got to be careful and keep your wits about you.
"It pays a lot better than the streets."
A first-ever study of the underground US sex industry in 2014 showed that many sex workers now prefer to make transactions over the internet where rates are higher and they are less vulnerable to arrest or assault.
Meredith Dank, senior research associate of the Urban Institute, which carried out the survey for the US Justice Department, said there was "a higher price point" for sex sold over the internet.
Some sex workers say the internet enables them to take 100 per cent of profits in place of sharing them with pimps or escort agencies.
According to one sex worker who advertises online, "business is booming".
"It's just more discreet than it used to be," she said.
"A lot of the girls used to stand around getting picked up and dropped off but now we can do the same jobs without having to take all of the bullsh** ... although there's still some of that from time to time."
The woman said street sex workers were often heckled by drunk passers-by and patronised by others.
"A lot of the girls don't like the looks and upturned noses that comes with putting yourself out there," she said.
"You skip all of that degradation crap by going online and there's also wider access to more clients.
"At least if you're advertising escort services online you don't have to operate in the shadows and there's going to be a phone number or IP trail between you and the person who contacted you if something happens."
It's a trend that has extended to other cities and regions across the country, and worldwide.
But street prostitution is still rife in many places across the world, including Melbourne's red light mile. A number of sex workers were murdered and discarded after being picked up from the area in the 90s. Some of the murders have remained unsolved for nearly 30 years. It's a stark reminder of the dangers sex workers face, on and off the streets.
