As a writer, one of my favorite parts of literature is that all words have baggage. You choose a specific word to elicit distinct feelings or meaning. For instance, if I write, “The family went out to dinner for tapas,” you probably picture one family. But if I wrote, “The family went out to dinner for pizza,” you’d probably picture a totally different family. They could easily be the same family, but words have baggage. Specifics matter.

Recently, I saw a TV commercial where the woman told her friend she was on her way to Milwaukee. It wasn’t a punchline. It wasn’t part of the story; the writer just needed to pick a city name that fit the tone and wasn’t distracting. 

It would have felt different if she said Vegas, Miami, or maybe even Cleveland. They all connote something different. Vegas means a quick wild getaway. Maybe a little spousal cheating. Miami means a sexy party. Maybe a little drugs and dancing. Cleveland means a low-budget vacation where you also have to visit family. Maybe some nice appetizers and bowling. But she said Milwaukee.

First, it made me smile. It makes me happy whenever I see Milwaukee not being used as a punchline. Second, it made me curious.

I wondered where else Milwaukee is mentioned in pop culture. Not where it’s a plot point or a setting, but just a random reference. And what is that reference saying about Milwaukee? In what context is Milwaukee being used?

Let’s start with probably the most popular Milwaukee reference.

I love this. But why Milwaukee? First, they needed to pick a bigger city than Aurora, where Alice Cooper could tour for Wayne and Garth to drive to go see. Why not Chicago? I like to think it’s because Milwaukee is more fun, more interesting. More random. You certainly don’t get the same laugh if Alice Cooper knows all about Chicago. And Milwaukee is, well, it’s cool.

It was so cool it led to former Mayor Tom Barret naming Friday, October 1st Alice Cooper Day and Mike Myers wearing a "Mil-A-Wa-Kay Algonquin For The Good Land" shirt by Brew City during a Wayne’s World virtual reunion in 2020.

Next up, let’s talk about Love Actually. For the haters who haven’t seen it, there is a subplot where the character Colin, played by Kris Marshall, can’t woo a woman in his homeland of Britain. He decides to go to an American city where he thinks his accent will be an aphrodisiac. He arrives in Milwaukee, Wisconsin, where January Jones, Elisha Cuthbert, Ivana Miličević, and their roommate, Shannon Elizabeth, are immediately smitten.

Why Milwaukee? Because they needed a place where a nice British guy could find some nice, average, not overly cultured ladies and be kindly accepted. A midwest “Americana” city that wasn’t too big but internationally recognizable and that didn’t have any negative baggage. Bullseye, Milwaukee.

Of course, not every Milwaukee reference is random and innocuous. It’s true, Milwaukee likes beer and cheese. So we should expect some blowback. It’s fair.

Like in The Simpsons, when Springfield became the fattest city, and Homer yells, “In your face, Milwaukee!” Or a joke mocking Milwaukee in Futurama (also by The Simpsons creator Matt Groening) when the Planet Express crew arrives at “The Most Romantic City on Earth.”

Some references seem just plain mean. Which brings me to Dogma, Kevin Smith’s religious tour de force. When asked if a pair of fallen angels were sent to hell, the angel Metatron responds, “Worse, Wisconsin.” There we see the angels, played by Ben Affleck and Matt Damon, in the Milwaukee airport (shot at the Pittsburgh International Airport, BTW) trying to convince a nun that God doesn’t exist.

Seems like a real fuck you to the 414, huh? Well, hold on a minute. Why did Smith choose Milwaukee? Because he got screwed over in Milwaukee once? Maybe the Milwaukee Film Fest didn’t accept Clerks? Possible. But not probable. I think he chose Milwaukee because … it’s funny. It’s totally random. I think it’s less of “Milwaukee is a shithole” and more of “Milwaukee … just a random Midwest city.” What if they were sent to Chicago? Or Denver? I don't think the joke would hit. But Milwaukee, and Wisconsin, have the baggage of being a “nice” place full of cheese. There’s the joke. Where would you send two angry fallen angels looking to mess shit up? The random, chill, friendly city of Milwaukee.

However, along my Milwaukee pop culture journey, I didn’t find as many jabs at The Cream City as I expected. The more references I found, the more my hypothesis stands. Milwaukee is referenced because it’s the funniest choice for a random, mid-sized, Midwest, recognizable city that people generally have a positive attitude towards. It’s like, everybody knows somebody in Milwaukee. 

Let’s look at a few more examples.

Captain America: The First Avenger; his tour takes him through Milwaukee.

The Incredible Hulk; Stan Lee’s character that drinks a soda with a drop of Bruce Banner blood in it (to dire consequences) is from … Milwaukee.

Anchorman: The Legend of Ron Burgundy; when Ron Burgundy is distraught over losing his dog, Baxter, he gets a call with no answer and hopes it’s Baxter saying, “Bark twice if you’re in Milwaukee!”

Monster House; one kid tells the cops he’s on their side by saying, “My cousin’s a cop in Milwaukee. Well, he’s kind of a cop. He’s got a gun.”

The very random 1994 movie Camp Nowhere; two twins argue about which city to bomb:

Rugrats; Angelica has an imaginary twin named “Ballina” from Milwaukee.

10 Things I Hate About You; here’s how Heath Ledger's character comes clean about his lies:

Rick and Morty; Beth and Jerry first kissed during a Milwaukee Symphony Orchestra concert.

Friends; When sharing the weirdest place they’ve ever had sex, Phoebe says it’s Milwaukee.

Reservoir Dogs; Mr. Orange and Samuel L Jackson figure out one of the thieves is from Milwaukee because he bet on the Brewers.

Ted Lasso:

Up the Air; Vera Formiga’s character tells George Clooney’s character, “I know a killer burger in Milwaukee.”

Seinfeld; a Yankees player asks George Costanza, “Are you the guy who put us in the Ramada in Milwaukee?”

Reboot; Hulu’s show about writing a TV show.

And here’s my personal favorite of the quick random references. In the Sci-Fi’ish cult classic TV show Mystery Science Theater 3000, in Mike Nelson’s final episode, “Diabolik,” he and the bots escape the Satellite of Love and their evil captors who made them watch cheesy movies, the worst they could find (La! La! La!). They end up in a garden-level apartment in Milwaukee, watching cheesy movies together.

But wait. 

As I dug deeper, I found something I didn’t expect. And it started with iCarly, the Nickelodeon series from 2007, which I REALLY didn’t expect.

In season four, episode five, “iDo,” an iCarly fan from Wisconsin asks if he can propose to his girlfriend on the web show. Which opens the door to plenty of Wisconsin ribbing. He offers her some Wisconsin mustard; “It has beef in it!” She accepts the wedding proposal by saying, “You bet your cheese I will!” Then the iCarly cast is invited to the wedding in Wisconsin, which they hate! Maybe there were more jokes. Probably. I don’t know. I got eight minutes into the video and just couldn’t do it anymore. Sorry iCarly, but not really. (If you hate yourself, go for it, and report back!)

Fine, iCarly, you got us. But this episode of iCarly is not the only one that comes up when you search the internet for iCarly and Milwaukee.

A season earlier, in episode 13, “iSpaceOut,” an eccentric billionaire invites the iCarly crew to do a web episode from space, and they have to travel to a facility where … well, I’ll let the iCarly writers say it themselves because it’s just too funny … “This is one of the main rooms where we evaluate people’s testitude to see if they can handle space travel.” Wow. Great writing. Really nailed it there.

Why am I mentioning this? Because when they cut to the exterior shot of this high-class expensive state-of-the-art facility, it’s actually … the exterior of the Milwaukee Art Museum.

Guess we’re not a bunch of cheese-eating lame-o’s after all, huh, Carly?!

In fact, I discovered when “Milwaukee” is spoken, it’s to reference a random but recognizable, positive Midwestern city. But when Milwaukee is shown, it’s a high-class, high-tech, absolutely stunning location.

Check it out:

In Transformers: Dark of the Moon, the Milwaukee Art Museum is the headquarters of the billionaire antagonist. Shia LaBeouf’s character even called it a beautiful building: “It’s like the Starship Enterprise in here.”

This Victoria's Secret ad uses the Milwaukee Art Museum as the backdrop to show off its new bra with a “miraculous push up [that] instantly adds two cup sizes!” Makes sense. I always say there’s no better place to show off the power of big beautiful boobs than the Calatrava.

On The Circle, Netflix's reality competition show about social media, they used B-roll of Milwaukee (they did not film in Milwaukee) to give off the vibe of a modern, hip city.

Okay, so yes, most of them are from the Milwaukee Art Museum, but still! And it is the logo for our tourism organization, Visit Milwaukee.

There is one final reference I want to share. One that both references Milwaukee and shows Milwaukee and is probably the most honest version of both. It’s in Adult Swim’s Joe Pera Talks With You. For those that don’t know, Joe Pera Talks With You is a quirky, relaxing, alt-comedy show starring Joe Pera, a comedian playing a "soft-handed choir teacher" from Marquette Michigan, named Joe Pera. In season two, episode 11, “Joe Pera Shows You How To Do Good Fashion,” Joe and his cameraman Gene travel to Milwaukee, where Gene’s sons are putting together a fashion show, which he doesn’t understand.

Overall the episode really is a funny love letter to Milwaukee. It even has a mini monologue touting why Milwaukee would be a great city to move to, starting with, “It’s no London, but it’s no Cleveland either!”

At the beginning of the episode, on their way to the Domes, Joe and Gene stop at the Milwaukee Art Museum. There is a beautiful and lengthy shot of Joe and Gene quietly standing at the end of the Reiman Pedestrian Bridge in Museum Center Park, admiring the museum. Then, they have this exchange:

Milwaukee definitely has problems, but we’re also a place where British dorks can share a night with January Jones. Where Beth and Jerry Smith can have their first kiss. Where half-naked Victoria's Secret models and billionaires roam the art museum. We have work to do, but we’ll also always be “the good land."

And hey, at least we’re not Cleveland.