The Roppongi of legend was back in the 80s and 90s. The 90s appears to be the peak of wild times. That's when you went to clubs and hooked up for first night sex. Lots of alcohol, ecstasy, marijuana, etc... behind the scenes. High school girls getting banged and even paid. Sex outside, on rooftops, on stairs, in club bathrooms, etc...
In the 2000s, Roppongi started slowly dying. But 2000 to 2007 still had plenty of wild times (with 2000 to 2003 being wilder). Not quite the wild crazy times of the 90s, but still kind of wild and crazy. Lots of stories from this time period. Wild Russians and Eastern European women, Brazilians, Swinger sex orgies, still lots of wild sex, Pride (MMA) fighters walking the streets of Roppongi, partying hard until 11AM in the morning or just not stopping for days, etc... The election of Governor Ishihara, particularly his 1st re-election would be the harbinger of bad times and bad days for Tokyo. Nutty right-wing racism and anti-foreigner propaganda gets a firm foothold and goes more mainstream over time.
2008 is when things hit the toilet. Markets were crashing everywhere, jobs with crazy salaries and fat cat expense accounts started to dry up too. As the money went, the international flavor started to die, and people started leaving. Also the anti-foreigner and racist policies of right-wing Governor Ishihara stated to take it's toll even more with immigration crack downs and restrictions... Things were coming down, but during 2008, everything came tumbling down hard. 2008 also marked the rise of Roppongi scam artists. They were always there, but they became worse than ever. The rise of the skinny Japanese metro-sexual and ambiguously gay guys...
2011, Fukushima and the Earthquake. Roppongi night life nosed dived and became total shit. Roppongi becomes anti-sexual. Wild adventurous and passionate sex dies. Now, all about your money. Scams of every kind become even more prevalent. Right wing anti-foreigner Japanese propaganda dominates the minds of many Japanese, but on the flip, the world is more international and interconnected than ever. So a kind of double-mindedness permeates. Roppongi becomes a rip-off town. All about scams, ripping off, cheating, lying.... Not worth it at all. All the smart pickup artists, with a clue, stop hitting the clubs and start hitting the streets (where the experts were always at). Girls scamming guys for drinks, not hot sex, becomes the new Roppongi game in town. Japanese women in lesbian-like groups become more prevalent in the clubs. The rise of the sneakier, ambiguously gay, and non-sexual younger Japanese generation becomes more prevalent. Brown and yellow hair dye among Japanese a big hit.
Present- Roppongi is totally shit. The Tokyo club scene in general is dead. The small fires of the old days and old ways burn in the hearts of the older wise cats who play among the disaster and still find entertainment. Some exciting times can be had, but you must now be or become really good at finding them. Adapting a more pickup artist type style is what works in the city now. Especially with the sneakier, quasi-conservative, public image conscious, and ambiguous younger generation. You have to find it and make it happen, not expect to walk into a club full of it.