It’s the kind of place that draws you in, sometimes unintentionally. You might be having a few quiet drinks in the city and next thing you know, the sun is coming up and you’re fighting for a cab (or a kebab) on Bayswater Rd. It’s kind of like the Bermuda Triangle of Sydney. Most people experience a mysterious memory loss, sometimes permanent damage and often find themselves waking up next to more than what they bargained for. But who says this is a bad thing? In short, just roll with it, let it suck you in, spit you out and bleed you, and your wallet, dry.

From the late 80s, Kings Cross was known as “The Golden Mile”. This was the period when criminals, prostitutes and corrupt cops ruled the streets. It was Kings Cross at its most dangerous: seedy and drug-infested, and many would say, it was the Cross at its best. But a commission into the corrupt handlings of the NSW police in 1995 made all of the glory run through the hands of the law. Many policemen and women were shamed and could never work again. Others fled, and some of the truly affected committed suicide.

Since then the Cross has cleaned up its act and while there are elements of the old Golden Mile that keep its reputation as a seedy, violent and sex and drug-filled underworld, it’s just a great place to go out now. You’re more likely to see football teams, rather than gangs; police rather than pimps; and scantily clad students, rather than prostitutes – although it’s hard to tell these two types apart.

But don’t despair, you’ll still see the odd tranny-hooker, some wheelings and dealings, fights and hustling, it’s just not the playground of yesteryear where you could get away with almost anything. You’ll find the crowds are full of young, liquor fuelled-revellers who want to have a good time. The Cross lures them in like horses to water. If you think you fit the bill, read on, if not, well you never know, it may just be horses for courses.

Piano Room

THE LOWDOWN: If you’re really trying to impress someone, Piano Room, (yes it has a piano, but no, I’ve never seen it played) is a standout. It looks like a decadent New York City cocktail lounge and has sweeping views of the Cross through the wall-to-ceiling windows. Stay for the view, but don’t get too cosy unless you have the funds of a New York City banker.
WHERE: Corner of Kings Cross & Darlinghurst Rds
pianoroom.com.au

The Sugarmill

THE LOWDOWN: A fairly new pub with a trendy, slick feel to it. Attracting everyone from backpackers to businessmen to locals, it is the kind of pub that unites us all. Probably because everyone likes a $10 steak, drunken karaoke and extended happy hours. The old-school bohemian theme is infused with modern street-press music posters on the wall, so depending on which way you sway, there’s a nice balance that isn’t overly pretentious. Oh and did I mention the $3 beers?
WHERE: 33-35 Darlinghurst Rd
sugarmill.com.au

Whaat club?

THE LOWDOWN: Occupying the old Le Panic site on Bayswater Rd, Whaat Club? because it doesn’t yet have a name, is owned by next door’s Candy’s Apartment. The cover charge into Candy’s will get you entry into this club and probably give you a well-needed break. It’s more intimate than Candy’s and has a great outdoor area where you can watch the trash rolling down Bayswater Rd. Before you whip out your illuminate recycling vests, I am referring to the people.
WHERE: 20 Bayswater Rd
candys.com.au

Twenty One

THE LOWDOWN: This club opened last year and is owned by the self-proclaimed “King of the Cross”, John Ibrahim. If you get through the exclusive door policy (read: you’re not blind drunk) you’ll be rubbing shoulders/throwing punches with footballers and other minor Sydney socialites. These guys are the new kings of the underworld, just pick up a newspaper on Monday morning and check the headlines, guarantee one of them has been in a fight/been caught with drugs/been caught urinating on a cop car. Classy guys, footballers.
WHERE: 12 Kellett St
twentyonesydney.com

Hugo’s Lounge

THE LOWDOWN: Similar to Trademark, lots of posing from models, quasi-celebs and the beautiful people. They look over the scum from the balcony with their noses held high. They might think they’re better and maybe they are, there’s always someone in my group that gets refused entry. It’s no wonder Hugo’s goes by the nickname “Huge Egos”.
WHERE: Level1, 33 Bayswater Rd
hugos.com.au

The Roosevelt

THE LOWDOWN: This new “small bar” is giving the Cross a good reputation, with it’s Mad Men like decor and its hot, talented bartenders who whip up fancy cocktails using liquid nitrogen like they’re magicians. They’ve also got a drink served in a gun proving alcohol and firearms can go hand in hand. It’s pretty hard to get a table in this place, and will probably be like that until there’s a new kid like it on the block.
WHERE: 32 Orwell St
theroosevelt.com.au

Candy’s Apartment

THE LOWDOWN: Next door to World Bar is the seedy underground nightclub known as Candy’s Apartment. Step back into a debauched world with Andy Warhol-inspired décor and some of Sydney’s most up and coming DJs. If anything, they’ll keep you up until 6am.
WHERE: 22 Bayswater Rd
candys.com.au

Trademark

THE LOWDOWN: If you just want to spend the night posing with the hope of making the social pages, you can do so at Trademark. This establishment also houses Piano Bar under the famous Coke sign. But it’s a lot friendlier and not as pretentious. 
WHERE: 1 Bayswater Rd
pianoroom.com.au/trademark

World Bar

THE LOWDOWN: Ah, backpackers, the Cross lures them in like a horse to water. And these horses sure can drink. World Bar is very popular among travellers. That might be because its name suggests racial harmony… or maybe it’s because of the happy hours, three levels of fun and its signature drink – the cocktail-filled teapot. Open all day and night, which is perfect because sipping out of a teacup is the norm at any given hour.
WHERE: 24 Bayswater Rd
theworldbar.com

Empire

THE LOWDOWN: Don’t dismay, there’s a bar where everyone is welcome and will satisfy those Britannia cravings. Lots of Brit-pop on rotation, continual drink specials and late night cheesy pop anthems to get you in the mood, it must be the number one hook-up spot for desperate backpackers. No need to walk 500 miles for love, they’re right here at Empire.
WHERE: 32 Darlinghurst Rd
empirehotel.net

Goldfish

THE LOWDOWN: Named for its ample people watching abilities many years ago, the Goldfish Bowl has since been renovated. Although it’s now harder to see into the bar, the people in there are much better to look at. Go figure. Opposite the Coke sign, it’s now just called “Goldfish” and has a much better vibe, cocktail list and decor. The opening hours are still just as good and the bar always seems to be packed at 6am on a weekend when all the other bartenders from the area are letting their hair down.     
WHERE: 111 Darlinghurst Rd
thegoldfish.com.au

The Bank

THE LOWDOWN: In the thick of Kings Cross, between kebab shops and strip joints lies this surprisingly classy joint. Named after the bank that used to occupy the premises, it’s a plush, sophisticated bar that attracts a high class crowd. For the rest of us, well, we just feel robbed. Snap.
WHERE: 42 Darlinghurst Road
thebanknightclub.com.au

Kings Cross Hotel

THE LOWDOWN: The Cross loves to reinvent itself. Another makeover has been given to the Kings Cross Hotel, which, on the corner of Darlinghurst Rd and William St, is kind of like the entrance to the amusement park that is the Cross. It used to be a dive, but now it’s five levels of pure fun with bars, nightclubs and a 24-hour licence. Plus, on level five you get an amazing view of the glitzy strip and the Coke sign across the road.
WHERE: 248 William St
kingscrosshotel.com.au

Iguana Bar

THE LOWDOWN: Hidden away in the back streets, this sweet little bar is open until 6am on weekends and is a great place to unwind at the end of the night. With great lighting, booths and interesting art on the walls. If you’re unable to bring much to the table in terms of conversation at this hour, at least everyone will have something to look at.
WHERE: 15 Kellett St
iguanabar.com

Mansions

THE LOWDOWN: Kings Cross caters for everyone. Say for instance that you like playing bingo or, perhaps, you like men who dress up as women. Well, tick both of those boxes at Mansions Hotel. Trannies like Penny Tration drop their balls from 8pm every Thursday night. Anyone for number 88? Two fat whores.
WHERE: 18 Bayswater Rd
mansionshotel.com.au

Showgirls

THE LOWDOWN: When the games end and you don’t fancy the ladies at Empire, the strip clubs will be calling you in… literally… the doormen will be begging you. “World famous” Showgirls houses the best erotic dancers in the country, with nude table-top dancing, private rooms and hostesses who will be at your beck and call – for a price of course.
WHERE: 41 Darlinghurst Rd
worldfamousshowgirls.com.au

Bada Bing

THE LOWDOWN: At the other end of the spectrum is Bada Bing, more of a relaxed, buck’s night kind of establishment with girls who are experts in the art of pole-dancing. But make sure you buy your tokens if you want to guarantee an eyeful, these ladies won’t let you sit front row for nothing.
WHERE: 70 Darlinghurst Rd
badabingnightspot.com.au