Bootleggers, also known as Boots, is an Oakland establishment. A large group of us went around 4:30pm on Saturday and we had the whole place to ourselves. Our bartenders, Jerry, did a great job of taking care of all of us. The prices were insanely good - my seltzer was $3. I like how they have a back room with a couple of grungy pool tables and a dart machine so that we could play games. I don't know who controls the music but they're definitely a Swiftie which I loved. No food, but I wasn't surprised. Would come back when it's chill like it was when we went! read more

Bootleggers - They have darts! - A dart machine with a digital scoring screen and electronic dartboard is positioned against a brick wall in a bar or pub environment. - Dive Bars Near Me - Pittsburgh, Pennsylvania

See all

Fun. Old school. No frills. Super-fun. A Pitt student staple. Pool tables could be refinished but that's nitpicking!!

If you give a bad review for a place like this it's more about you than the bar. Good pours, mellow vibe. Just a good neighborhood dive bar. read more

I wish I could give this place zero stars. The bouncer and acclaimed owner known as "Junior" is extremely confrontational and ignorant. Egocentric would be an understatement. My friend and I who are both of age attempted entering Bootleggers on St Paddys night. The bouncer spent a few seconds looking at our IDs, and instantly denied us entry. We asked the bouncer to scan or recheck the IDs, given we were both of age, at which point he began bending my friends ID so much; to the point that the plastic card almost physically snapped. While trying to do so, the plastic film on top of the real license began to peel in the middle. He claimed that "a real license wouldn't do that" but I threatened to call that the cops if he wanted me to prove it and went ahead and did. After waiting for 25+ minutes, the cops never showed up so my friend and I just decided to leave. I did not want to waste the cops time on such a small matter, and decided to just leave the establishment with a broken real ID. If you want denied entry and a real ID snapped in half, this is the place for you. read more

As dive bars go, I have a special place in my heart for Bootleggers. I've spent roughly 1/3 of my life drinking cheap drinks here with friends, eating some hot wings, and playing pool/darts. We still make trips here every now and again even though we don't fit in with the college crowd anymore, and I still love it here. read more

A-hole bouncer and presumably the owner known as "Jr." was relatively chill the whole night with guests until he became too drunk to actually function. He was taking shots with guests and carrying on rather than doing his job. I was just standing near the bar carrying on with several patrons that "Jr." was also having a good time with and then out of the blue, he grabbed a guest by the neck and pinned him up against the wall. And then when that situation deescalated, he came back my way and grabbed me by the neck and threw me out the door for no good reason as I had no involvement in prior situations. He was aggressive towards several other guests as I waited outside for my friends. I would not recommend this establishment to anyone who wants to be treated with dignity and respect because none will be given to any paying customer. read more

I had a great experience besides the bouncer, the bouncer started pestering us as we had a drink in our hands 20 minutes before close. He then decided 10 minutes before close that we couldn't be there as we were drinking our beers. We where just sitting at the bar drinking and he came specifically up to us to ask us to leave while 20 plus people sat at the bar. We realized it was late and decided to leave but as we talked while leaving he decided to think we were saying stuff about him so he then got in our face and yelled at us to leave. Seriously awful customer service. I understand asking to leave around close but its a Saturday night and I don't see my friend often plus the bar has not closed yet. He seemed either really drunk or high on marijuana as he couldn't make eye contact and just used his tall frame to push us out. He was chatting with regulars/friends while extremely hostile/ rude towards anyone else. I really don't understand why people would deal with the abuse. Great bar besides this one awful bouncer. read more

Boots has the cleanest ashtrays in all of south oakland. I swear to god their amazing bouncer Chris Ragle goes table by table and caresses those sweet bad boys with his tongue and licks them clean. read more

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. read more

Bootleggers - Tuesday Night - Dive Bars Near Me - Pittsburgh, Pennsylvania

Cheap beer, $6 for a pitcher, and fun pool tables in the back. Even for being in Oakland it isn't too much of a college centered bar like GDoor or Hems. Overall had a really great time! read more

We decided to try this place, because it seemed low-key and we didn't want to go far from Oakland. It's a pretty simple bar with televisions, two pool tables, and darts. The bartender was awesome. They even had free Bud Light for the night. They don't serve any food, but they allow you bring in food from other places. It's conveniently located across the street from Larry & Carol's and Campus Deli. If you ask the bartender, they'll provide the menus for those places. Cool atmosphere at first; it did get packed and loud around 11:00pm or so. It was a live place to watch some college football, munch on good food, and drink cheap (but good) beer. Guinness, Blue Moon (including Pumpkin Ale), Angry Orchard, and more all on tap. read more

This is a good bar but the bar tender was mean to me and didn't get me my drink and also did not get me water when I asked for it and I feel like that is just uncalled for. It was obvious she was overwhelmed because she was busy but she was being straight up rude and not friendly. read more

Love this place and their scrumptious drinks. My friend shaye enjoyed them so much she went behind the bar and curled under the counter. And rumor has she's still there to this day, so go say hi. read more

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 karaoke 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. read more

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. read more

This is the second time my friend who is 21 years old got rejected from this bar. Not only was she embarrassed by the bouncer accusing her of having a fake ID, but we ALL as a GROUP were treated like second class costumers by the bouncer for absolutely no reason other than her having a different haircut in her ID than she had now. This business needs to 1. Learn how to spot an actual fake ID and 2. Treat patrons with more respect. I don't think I'll ever come back here. read more

I do not acknowledge the name "Bootleggers". This magnificent property is and always shall be known as "SOD". Back when draught Schaeffer was 35cents and ""You shook me all night long" was eternally B2 on the June box, you could play that twice, drink 2 beers and still have a tip. God; how I miss those wondrous days. read more

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 karaoke 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. read more

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. read more

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. read more

My boyfriend and I recently went to bootleggers to see if we could get dinner and drinks... well it was what we expected it was early so as expected an older crowd- pool tables, darts and in door smoking. The (what I'm guessing is the owner) was attending at this time and was really nice, somewhat hard to understand but all around welcoming. What really threw us off was the fact that we read the menu online prior to going and apparently their kitchen is only open on thursdays??? Idk if this is a common thing or what but personally I have never heard of a pub that's kitchen is open one day a week. If you're going for drinks and darts it's great but the kitchen thing really killed my vibe. read more

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 menu items, unclean tap lines, flat beer, "regulars", wobbly tables, and a cigg machine). But otherwise it's 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. read more

Bootleggers is our go-to bar after softball games in Oakland. It is cheap, easy to get a drink, and great location. There is lots of seating around the bar and they often open up the windows on nice nights which always earns extra points in my book. I have never once had an issue with service there. I don't understand why people would rate them low just because it is divey. Sometimes you just want to knock back a few Miller Lites with your friends and don't need a fancy menu or extensive beer list. read more

I like this bar but out of 4 times I've gone, the bouncer has told me my id was fake twice. If it happens again I'll never go back. I understand being safe but I have a LEGITIMATE ID please let me into the damn bar. Being from Ohio does not mean an ID is fake read more

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 read more

Five stars for what is.... the best local watering hole in Oakland, maybe anywhere. It's a dive, but there's cheap drinks, pool, and darts. Also a great crew who works there who actually enjoy being there. If you are expecting it to be something it's not, yeah, you won't write a good review (like some here on yelp). But if you are just looking for a local, chill, smoking, hangout bar to watch the game and/or shoot some pool and throw some darts, this place can't be beat. read more

This is easy the best dive bar in Pittsburgh. Staff is is always incredibly friendly. Drinks are very reasonably priced. Darts and pool is available. I spent time at this bar nearly every day when I was at pitt. To get the best experience come on a Thursday night when they have wing night and get some wings to go with you darts and beer. read more

This bar is really nice if you just want to hang out with friends or take a date too. They have really good drink specials and an amazing staff. They even serve wings on Thursday nights which taste pretty damn good. Mostly every bar tender there is really nice and knows how to make every drink. The doorman there are nice and fair and will talk to you if you have an issue. The bar even has pool and dart games. It's great for groups and they even have a dance floor. I love going to this place and every time I do I have a great time. I've got to know some of the workers there and they are really good people. The bar tender Ben is a nice guy and manages the bar very well. Also the bar tender Frank might be the best bar tender I've ever had. He's a really funny guy that you can have a great time with. He also knows how to make any drink you want. I definitely recommend this bar for everyone. You will have a great time there. read more

This place feels like home. It's a dive bar that tried to ascend beyond "dive", but ultimately realized what they were at their core. Sure, it gets crowded with millennial students on weekends, but ultimately it has friendly staff and a welcoming atmosphere. If you're looking for a place to meet one night stands, look elsewhere. If you're looking for friends and cheap booze, you couldn't find a better place. The "Cheers" of South Oakland. read more