In A-side/B-side, two Milwaukee Record writers tackle various city issues in an informal and hypothetical crosstalk style.

Tyler Maas: I have a question for you, Matt. I must admit, it’s kind of a strange one, but it’s something I’ve been thinking about for weeks and have enjoyed discussing with a few people. I think you’ll enjoy it, too, and it might even inspire a wide variety of comments and suggestions from readers. Here it goes…

If you had to pick one Milwaukee street—any street at all—to spend the rest of your life on, which would you pick? Before you answer, I have to add some rules and stipulations that need to be followed:

• You can pick any place to live, but the address needs to be on that street or property needs to touch said street.

• It has to be in Milwaukee proper. For example, if you pick Oakland Ave., you don’t get to enter the Shorewood portion. Your North Ave. territory would end at the Wauwatosa border. National Ave. doesn’t include West Allis amenities. You get the point.

• Any food, goods, or services you receive must be provided on that street. No delivery allowed.

• Money and career are of no concern—just don’t leave that street.

That’s pretty much it! Refusal or death in order to avoid this fate are not options, by the way. So with all that in mind, what’s your selection and why did you pick it? Like I said, I’ve been pondering this for some time, so it’d be rude for me to go first.

Matt Wild: Fun question! And one, weirdly, I’ve been thinking about a lot lately. To explain:

Ever since I moved out of the UWM Sandburg dorms in 1974, I’ve lived in the Downer Avenue/Murray Hill neighborhood. I’ve lived in about a dozen different apartments, mind you, but always in the same neighborhood. Recently, my family and I were discussing moving. Maybe we should get a house? Move to Bay View? South Milwaukee? Maybe Cudahy? That’s what people our age (early 70s) are supposed to do, right?

Wrong! The more we talked about it, the more we realized that our longtime neighborhood—specifically, the neighborhood surrounding the two blocks of Downer between Park and Webster—was so ridiculously stuffed with, well, stuff, that it would be pointless to leave. That two-block stretch of Downer has: one grocery store and one pharmacy/grocery store (Sendik’s, CVS); two coffee shops (Stone Creek, Starbucks); three restaurants (Café Hollander, BelAir, Canela Café); a hardware store; a liquor store; a bakery; a gym; an optometrist; a church; and, oh yeah: a movie theater and an independent bookstore (Downer Theatre, Boswell Book Company). There’s a bar right around the corner (Henry’s, which also has food), and a bubble tea place is set to occupy the long-empty Chancery space. Yeah, Pizza Man recently bailed for Humboldt, but hopefully that large, gorgeous, and wickedly expensive space will fill up soon. [tugs collar]

Now, are all of these places among Milwaukee’s absolute finest? Other than Boswell, which truly is the city’s best indie bookstore, I’d say no. But they’re all right there, on a short two-block stretch of East Side road, and they’re all fine! (I’ll save my sure-to-be-controversial “BelAir is perfectly okay in a pinch so relax with your ‘Worst Milwaukee Restaurant’ Reddit posts” thinkpiece for another day.)

So that’s my answer: Downer Avenue. Food, drinks, groceries, entertainment, and a new pair of glasses: it’s all right there! You never have to leave! What about you, Tyler? What’s your Milwaukee Dream Street?

TM: Not bad! Even when removing Henry’s—which technically doesn’t qualify because it’s actually on Belleview Place—from the list, the part of Downer you mentioned is a very solid two-block stretch. And don’t forget the northern portion of Downer also includes the UW-Milwaukee campus, which gives you even more dining options, a massive library, a theater, and oodles of green space. Plus you get those bike races! There’s no hospital on the street, but beyond that and limited live entertainment options, I think you could do a lot worse than Downer Ave.

Though I desperately wanted to be clever, I’m also going to be boring and go with the Milwaukee thoroughfare I live closest to. Kinnickinnic Avenue might not be a very original selection, but I think there’s a reason for that. Bay View’s main drag pretty much has it all. That stretch of pavement, which basically runs from The Bottle on the north end to Romans’ Pub (R.I.P. Mike Romans!) on the south, features more restaurants than I have time and digital column inches to name. Included in that restaurant roundup is The Vanguard (which rules and, ironically, makes one of my Top 5 local burgers), Crafty Cow (which rules and makes my favorite local chicken sandwich), approximately five outstanding pizza places that all specialize in different but altogether incredible styles of ‘za, and a handful of great Mexican places. Shit, I even have a solid sushi joint (Hungry Sumo, plus Sushi Yuki by the year 2037…hopefully) and some amazing breakfast places (Honeypie and Landmark Diner, respectively) in addition to the array of quality establishments I haven’t even mentioned.

Beyond the astounding dining options, I know I’d postpone my eventual descent into one-street insanity by spending my infinite money at KK’s two record stores (Rush-Mor and Acme), catching first-run and classic movies at Avalon Theater, killing time and enjoying quality coffee at the 1,000 cafes on the street, bowling and playing arcade games at Bay View Bowl, picking up literature at Lion’s Tooth and Voyageur (or the Milwaukee Public Library branch on the street), buying groceries at Outpost, and stocking up on alcohol from Siegel’s or Bay View Quick Mart. Speaking of booze, I haven’t event touched on the Kinnickinnic bars! Blackbird, Lost Whale, Highbury, and Patti’s Power Plant are all great in their own ways. And if I eventually tire of those places, I’ll have plenty more to pick from to shake things up.

If I’m going to be super pedantic (I am), I’d also appreciate being able to get gas at one of the street’s three filling stations and replacing tires at the infinitely awesome Mr. P’s Tires in case I don’t want to walk. Then again, the 15 bus line runs all the way down Kinnickinnic, so I’m set there. Also, there are places to get my hair cut, buy (admittedly mostly vintage) clothing, work out, and there’s at least an emergency clinic and a pharmacy if I have medical issues.

I’m extremely happy with my pick. However, I do recognize some shortcomings with my chosen street. While I’m sure local items will be in abundance at many KK bars, I don’t believe there’s a brewery or distillery on the street (1840 doesn’t count, commenters). Sijan Field, Morgan Park, and Zillman Park offer some outdoor amenities, but admittedly leave room for improvement. And though the street is painfully close to Lake Michigan, the only natural water body I’ll actually get to witness firsthand would be from the KK Bascule Bridge…assuming the “KK Can Opener” didn’t strike that day. Most notably, though, is the shortage of entertainment. I, too, would get an annual bike race, as well as the brunt of Bay View Gallery Night festivities, and the mighty Bay View Bash. Other than that, I’d be reliant on whatever places like Tonic, Acme Records, and URSA occasionally booked to fulfill my live music itch.

So I’ve gone on forever, but what do you think of my pick and, while we’re at it, what are some other streets you pondered choosing before landing on Downer? Over here, I was maybe thinking Water Street (Marcus Performing Arts Center, Cooperage/Boone & Crockett, river visibility, decent restaurants, and nice hotels to live out the one-street prison sentence in luxury) might be a place I could live out the rest of my days as well. If construction isn’t an issue, I could also totally make Humboldt Boulevard work.

Matt: Yeah, it’s hard to argue with KK. It’s all spread out a bit more than my Downer pick, but you’re right: it has a ton of stuff. And, like you said, a lot of that stuff is the best Milwaukee has to offer.

I’ll quell the howling hordes in the comments now and say that Brady Street was a close second for me. This is probably Milwaukee’s most talked-about street these days, and for good reason. Hell, the beloved Brady Street Festival is this weekend! And I can’t wait to see what happens with the whole “pedestrianize Brady Street” thing. Other streets I love: National Avenue, Maryland Avenue, Wisconsin Avenue, and Center Street. And Oakland Avenue, too, because it has Oakland Gyros and a Cousins within throwing distance.

This exercise has been fun, though it has made me realize I wouldn’t want to stick to one Milwaukee street for the rest of my life—the fun and satisfaction of living in a city is experiencing all of its streets. Before I left the UWM dorms in 1974 (okay, fine, it was actually 1998), my entire Milwaukee life was confined to a couple of quiet East Side blocks. A trip to Oakland Avenue—much less Riverwest of Bay View—felt like a trip to another world. I’m glad my love of Milwaukee has expanded since then. I look forward to expanding it even more in the years to come.

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