Bar Veloso---This famous bar doesn't look like much from the street...it's a small restaurant with a sidewalk patio, and mostly just standing space. It's always full because they have the absolute best coxinhas in the city (chicken and Brazilian cream cheese-- a little bit like ricotta, fried in batter) and the most inventive caipirinhas. I tried the Tangerine hot pepper (pictured) but you're safe with any flavour.
Filial do Empório Sagarana tem ótima seleção de cervejas e cachaças
Empório Sagarana—As a craft beer store/cachaça shop, the beer can be expensive, but you'll find brands you won't see at any other bar in the city. It's reminiscent of a library with the beer lined shelves and rolling ladder. Even better than the beer is the impressive list of cachaças, many of them small batch. A shot (for sipping, not shooting!) is around R$7-15 ($4-7).
Empório Alto de Pinheiros--Half store half bar, this place has literally every beer you can think of, and a lot you've never even heard of. Whatever you like: from fruity Belgian beers to coffee flavored stouts--and the foods to match, they usually have around 30 beers/ciders on tap (which change frequently) and hundreds of bottles.
Casa 92--This old mansion turned club in Pinheiros is a totally unique venue. Kitschy decor and several rooms/balconies in the house give it a unique vibe...not to mention the fact that they give out helium filled balloons to guests. With 3 bars, couches, benches, a pool table, foosball, and a couple of DJs spread out in the house, you get a different vibe in each area. Best time to go: Thursday-Saturday around after 11.
Drosophyla--Hidden on a side street in Bela Vista, Drosophyla is different from anything you'll find in the area. The back garden and bar area is huge, and along with a Spanish inspired menu you can get some of the most original cocktails in the city.
Caos on Augusta is crowded with antiques hanging from the walls and ceilings, is always packed, even on a Monday, and the bartender actually knows how to make a really Dirty Martini and Bloody Mary (rarities in this city.
Morrison Rock Bar, Vila Madalena--This rock club has cheap cover, cheap caipirinhas and always has a good band. They usually give their nights a theme (90s grunge, punk, 80s metal etc) and the covers are almost always well done. The crowd here has a lot of energy, so be prepared for a full dance floor, mosh pits, and occasional crowd surfing.