Bootleggers

I wouldn’t really even give this bar credit of being a «dive bar». More like a backflop who over-​rotated when trying for a dive. Its got some slight characteristics of a dive bar (smoking, shitty menue items, unclean tap lines, flat beer, «regulars», wobbly tables, and a cigg machine). But otherwise its pretty normal. (Pool. Multiple darts, nice TouchTunes, many flatscreens, good wings, attractive waitstaff, renovated interior, wetnaps with wings order, etc.) it basically is a place who’s whole schtick is dive, but really its a pretty decent place filled with a bunch of apathetic hipster millenials who wanna pretend they go to a dive bar on the reg. Sad.

Great spot to day drink on a Saturday! Jerry the bartender is a great guy..

Shittest bar in Pittsburgh only go if your desperate. Hemingway’s is way better, their bouncers and bartenders are nicer and less creepy. Bootlegger’s bouncer objectify women and I felt very uncomfortable but if that’s your thing go for it

It’s inexpensive, but it’s really small. I didn’t find anything special about it.

This is your standard college dive; it’s bro-​filled and the average age is about 21-​and-​a-​month, but for a shot and a beer? It’s pretty all right. I tend to come here on Wednesdays, which is their karaōke night. The rotations get quite long, but the crowd is pretty accepting, even of oldsters like me (and random Ancients like the dude who wears Christmas sweaters and rocks «Oh Sherrie» on a regular basis).
You’ll probably like this place better if you’re a smoker, seeing as it is a smoking establishment. It’s not so bad in the warmer months, when the front opens up into the night air, but when it’s cold? Bring your SARS mask, because the place is like a hotbox, hazy as all get-​out.
In summary, if you don’t mind being surrounded by reminders of your own mortality, then grab ten bucks, sidle up to the bar (if there’s room), and get three or four well drinks. This place does the job.

A dive if there ever was one. It’s smokey, it’s dark, it’s full of broke college kids and life long Oaklanders. Occasionally I’ll come on Thursdays for $ 2 any drafts. It’s a great deal to drink a few Brooklyn Brown Ales or New Castles. The only issue with this is that due to it being being a dive bar most people are usually drinking the standard, cheap light beer and the kegs of the better stuff usually ends up sitting around for a while. Occasionally I have been served a crappy beer but they always replace it at no charge.

Bootleggers is an alright place, but nothing about it makes it stand out to want me to come back on a consistent basis. For Oakland the bar size is larger than most and there is a room for pool playing in the back if that is your thing.
The drinks are cheap and every night they have some sort of special going. The crowd is a mix of college and older folks, so bootleggers doesn’t cater to the college crowd as much as the other Oakland bars closer to campus do. Except on weekend nights when they bring out a ridiculous DJ and have a semi dance floor. Come on Bootleggers, you are not a dance club.
Though I don’t come here a whole lot I’ve never had a negative experience.

Lose your cellphone here.
Everybody’s doing it.
So dark and so drunk.
(b)

Bootleggers is my favorite bar in Oakland, and I don’t know why. I guess it’s cheap, but so is everywhere. It’s usually not too crowded, but I tend to frequent on weekdays. It also is located almost directly across the street from my apartment… this may be the reason. Actually that’s a rather large part of it.
But aside from convenience, I like Bootleggers because it’s not trying to be something it’s not. I mean Pcaf is alright but the «dancefloor» is a sad attempt at creating a club atmosphere and the outside area is simply pathetic. Peter’s is WAY too crowded and it’s only because they give out viking hats. Garage Door is huge but never that fun. Bootleggers is… dirty. full of creepers. uses only plastic cups and doesn’t use a tumbler. will not give you an orange with your Blue Moon (they don’t have any). has horrible karaōke regulars, trashy bartenders with fake boobs, and what looks to be a patched-​up gloryhole in the bathroom. The list goes on. And I’m not afraid to admit that I love it and I almost always have fun here.
Note on those trashy bartenders… good luck getting served if you’re a girl. They are usually too busy flirting with dudes or occassionally pole dancing on the support beams (no joke). My favorite night is Sunday… Ladies’ Night! Dollar wells and beers for girls, and the bartender, the only dude bartender, is great. The door guys here are super friendly as well, despite having to deal with shitfaced students on a nightly basis.
Basically, while Bootleggers is still full of undergrad bros and hos, if you’re looking for a place in Oakland that’s fun, cheap, and you don’t mind that it’s the epitome of a dive, it’s your best option.

Bootleggers is a pretty standard dive bar: fairly quiet, great prices, a pool table, and a variable crowd. It’s not really one of my go-​to bars, I guess internally it just doesn’t have the charm of some other close-​by places. The specials are nicely priced: $ 2.00 or less for great beers and liquor drinks. If you’re looking for a quiet place to have a few beers or shoot some pool, this could be a good choice.

Facts:
1.) I ordered a round of Irish Car Bombs. The bartender proceeded to prepare our drinks by pouring the requisite half-​pint of Guinness, and then fisted the bottles of knock-​off Jameson and Baileys in one hand and squirted the liquors directly into the beer. «I thought you were going to put the liquors in a shot glass for us!», I commented. «We’re out of shot glasses,» she replied, «what’s the difference anyway?» The smart thing for me to have done would have been to slug the curdling mess down as soon as possible instead of arguing with the fake-​tittied bimbo behind the bar.
2.) Outside of the gym, I have never seen so many bro-​heims in cutoff shirts, basketball shorts, and backwards hats. In fact, there were more of these at the bar than there were females of any type. One of the more interesting patrons was a 60 year old drunk who bought me Yuengling at closing time. He even followed my friends home from the bar! (*yikes*)
3.) I thought, in April of 2010, I would be at a point where I’d never have to hear the god damn Cha Cha Slide by D.J. Casper again. («Two hops this time! Hands on your knees!»). I was so, so wrong.

It’s an interesting joint. You would swear you were in the middle of a residential area, then the place appears.
I found it on a Tuesday night, in the ‘Burgh for a couple of days. The beer specials are solid, and it made me smile to hear that any beer not from PA is considered an import.
Cross your fingers that Amy is working the bar… She’s a charmer.