If you were to ask me what the best burger in Milwaukee is, I would say something like, “That’s entirely subjective and I’m not answering that.” However, if you pressed me to tell you my favorite burger in Milwaukee, I would immediately say “The Big O at Oscar’s” without a moment of hesitation. You might disagree, but the 8-ounce black angus beef patty that’s topped with hickory bacon, chorizo, fried onions and jalapenos, chipotle jack and smoked gouda cheeses, and a side of house made guacamole is my personal high watermark of Milwaukee cheeseburgers. Just look at it!
In the nearly 14 years Oscar’s Pub & Grill (1712 W. Pierce St., 414-810-1820) has been in business, I’ve visited the Clarke Square restaurant on countless occasions. Every single one of those times* I’ve eaten at Oscar’s, I’ve gotten “The Big O” and have never once regretted my decision.
(*excludes Tuesdays recently)
Yes, this month, I decided to welcome a new Oscar’s menu offering into my personal repertoire for the first time ever. To be clear, I’ll never step out on “The Big O” when it comes to the burgers I’ll enjoy on Pierce Street. However, if it’s a Tuesday and the mood strikes me, I’m now willing to experience another one of Oscar’s apparent (and somewhat unexpected) areas of expertise. Tacos.
Every single Tuesday, Oscar’s Pub & Grill and its affiliated Oscar’s Winner’s Circle—like so many other establishments all over the city, state, and country that like alliterative promotions—offer a special on tacos. I’ve known about this for years. I’ve seen them being enjoyed by people on neighboring bar stools and adjacent tables for years. I’ve even been roasted by acquaintances I’ve run into at Oscar’s on Tuesdays for daring to get a burger at the burger restaurant instead of tacos. However, it’s now become clear that my loyalty to “The Big O” has gotten in the way of me taking advantage of this midweek meal deal. Until last week, that is.
Last Tuesday, I had a lunch meeting at Oscar’s—which is a short walk from our office—where I enjoyed yet another “Big O” and (another go-to of mine) a $3 “Mystery Beer” pint. The quick lunch meeting turned into a three-Mystery Beer-long hang, which inspired me to finally integrate a taco into my Oscar’s dining experience. It was the start of a new era. This ardent “Always Big O” orderer is no more. At least on Tuesdays.
A few minutes after 11 a.m. today, I returned to Oscar’s On Pierce to partake in some more tacos, this time without the accompaniment of my beloved burger for the first time ever. The Tuesday special is $1 per taco (asada or pastor), DINE IN ONLY. They’re served on corn tortillas, topped with onion and cilantro, and they come with red and green hot sauce in squirt bottles. Much like my burger take, I cannot and will not claim Oscar’s has “the best” tacos in Milwaukee because that’s strictly opinion-based. I can tell you they are so, sooooo good.
The steak in the asada tacos is tender, well-seasoned, and more abundant than you might expect from a dollar taco in 2025. When slathered in the acidic and flavorful green salsa, the combination of skirt steak, fresh cilantro and diced raw onion, and delicate corn tortilla, they’re undeniably awesome. The pastor tacos feature sizable hunks of juicy pork and pineapple pieces slathered in a smokey achiote paste and topped with the same winning combo of cilantro and diced onion on a pillow-like tortilla. The orange salsa carries them to even higher territory.
Though I’ve seen people take 10-12 of these to the dome, I had four today and felt content. Including my customary Mystery Beer and tax, my lunch came to a pre-tip total of $7.54. That’s kind of unheard of at a place of Oscar’s caliber. And heck, for only a buck a taco, you could always start with a burger, add a taco or two onto your order, and just take it easy on the fries. Choose your own path! When a place truly excels at two things, it’s good to know you have options.
THE $1 TACOS AT OSCAR’S PUB & GRILL: WORTH (TEMPORARILY) ABANDONING ONE OF YOUR FAVORITE MEALS ON EARTH TO ENJOY.
