Up the road is the Clovelly Hotel, a large pub popular with footballers and those who love them. The barflies included - before he fled to France - one Sonny William Williams, erstwhile Bulldog and one-time user of the toilet stalls along with the triathlete Candice Falzon, who was not his girlfriend.

The toilet rendezvous was once reserved for clandestine mano-e-mano encounters; now it seems the romantic venue of choice for drunk footballers who are feeling a little "toey".

Unfortunately for SBW, when he got cosy with Falzon in the stall, someone slipped a mobile phone under the door, took a pic and flicked it on to the tabloids.

There's no plaque marking the infamy and I can't tell from the picture whether the scene was taken in the left or right cubicle. Try as I might, I can't lure my companion - or anyone else - into the loos for a bit of rumpy-pumpy. The only rump we have is the steak downstairs. We should have next headed to Macquarie Street, to room 803 of Parliament House, in particular, the suite once occupied by the member for Kiama, Matt Brown.

For four days he was the minister for police until reports surfaced that he had danced during a post-budget party in "very brief" undies on a couch to "Oxford Street techno" while performing - strongly denied by everyone involved - a simulated sex act on the hitherto undesired member for Wollongong, Noreen Hay.

Given the Milton Orkopoulos scandal and Nationals MP Andrew Fraser's penchant for disgracing himself on the floor of the house - pushing another MP late last year and lunging at Virginia Judge in 2004 - Parliament must have the highest scandal rate in the city.

We skip to the site of another great, drunken political downfall, the Hilton Hotel on George Street. Shortly after Bob Carr resigned his lengthy premiership, his opponent, the otherwise sensible John Brogden, went to the underground Marble Bar, where he pinched one journalist's bottom, made suggestive comments to another and referred to Carr's Malaysian-born wife, Helena, as a "mail-order bride". It took a while to come out but his political career was history. Again, no plaque.

I'm drinking with colleagues and a golden rule of boozing is never to fish off the company wharf, so re-enacting Brogden's bottom-pinching is out.

I just buy a round instead before heading to our next happy stop, Bar Reggio in East Sydney, where Rodney Monk, the former president of bikie gang the Bandidos, was gunned down three years ago.

Monk was dining with a fellow Bandido, Russell Oldham. They had a heated conversation inside and continued it in the laneway outside, where Oldham shot him, which is rather an extreme way to ensure you have the last word.

Three weeks later, Oldham shot himself. When we turn up to Bar Reggio, there's a long queue so we opt instead for the Gazebo in Kings Cross. It's the cylindrical former hotel that Barry Humphries chose in the 1970s as the scene for a spectacular bender after ending a year in a Melbourne psychiatric unit, before getting on the wagon for good.

Humphries managed to offend a number of prominent Sydneysiders, including the agent Harry M. Miller and the novelist Patrick White, who mentioned the ordeal in a letter: "Barry had burst into Harry's flat in Harry's absence and insulted the housekeeper by saying rude things about the paintings and furniture. According to Barry he was confused by his first day of freedom after a year of hospital. According to the housekeeper, he was drunk."

Humphries told White he had been "weaned off one or two toxic breasts" and asked him to a party at the Gazebo the following night.

White wrote: "I didn't feel I wanted to. Nor do I like to think what must have happened to Barry when faced with the toxic tits." The hotel is now an apartment block but there is a wine garden downstairs, a nice place in which to continue a Barry-style bender. In fact, it's too nice. It just won't do.

A few metres from the Gazebo, the Bourbon is a different world. There are tourists drinking, bogans drinking, gays drinking. Everyone is drinking. It is the epitome of a bender pub, takes all comers and has a considerable pedigree that even an expensive makeover couldn't shake.

In 1999, when still known as the Bourbon and Beefsteak, Ricky Ponting spent the end of a long night here and didn't it go pear-shaped? He hit on a woman, prompting an off-duty bouncer to hit him. He was knocked clean out.

The Sun-Herald helped jog Ponting's memory by publishing a photograph of him on the street, taken after he had come to; he was hugging a woman who was not his then-girlfriend. One report said the mystery bouncer worked at the nearby Vegas Hotel.

You wouldn't find radio host Todd McKenney dead in the Vegas, although police did find him in a state not far from death not far away. He was out to the world in Rushcutters Bay Park and discovered with a vial of gamma hydroxybutyrate, or fantasy, in his pocket. He was charged but later adopted the Matt Brown offensive play as a defence: he was dancing at a nearby party, got hot, so took off his pants.

He claimed someone must have put the fantasy in his pocket. Unable to prove he knew the drug was there, police dropped the case but McKenney scored a place in the long, long history of classic Sydney benders.