Singapore's nightlife is concentrated just south of Orchard Rd by the riverside, but there are still a few notable nightspots. The largest cluster is Emerald Hill (http://www.emerald-hill.com/) opposite Somerset MRT, a beautifully restored cluster of shophouse-cum-bars.
Alley Bar
True to its name, this bar has been set up in an alley between two shophouses — not that you'd really notice from the slick modern decor and the endless parade of Singapore's nouveau riche.
Number 5
Friendly bar housed in a 1910 Peranakan shophouse. Downstairs is loud, upstairs is quieter with a pool table. The cocktails are good, but for a fiery kick try their Chilli Vodka or its industrial-strength big brother, Chilli Padi Vodka.
A few places of interest lurk elsewhere along the strip.
Orchard Towers
Undoubtedly Orchard Road's most notorious nightspot, this building is a Designated Red-Light Area famously summarized as "four floors of whores". The first floor bars are borderline legit and not too bad for a noisy drink, but the rest are outright sleazy — and the Thai "ladies" propositioning passersby in the hallways may not be ladies at all.
Monkeys Cafe
Rock & roll themed bar serving cold beer, Oz hard cider and less hassle from the ladies. Indoor and outdoor seating, serves decent pub grub too.