In addition to being a longtime Milwaukee comedian, Sam Barone is also an appreciator of all things local. He’s passionate about Milwaukee comedy, Milwaukee music, and Milwaukee-based businesses. In late 2020, he decided to combine his comedic talent and his passion for all things local to start a monthly variety show. That show—called “Milwaukey To The City”—brings a late night TV format to the backyard of Champion’s Pub (or to Promises in wintertime) one Tuesday night each month.
With Barone acting as the host, an audience gets to know a local comedian, is introduced to a area musical act, and learns the inner workings of a Milwaukee-based business. There are games, video segments, trading cards, stickers, awards, and oodles of localized laughs. In advance of Milwaukey To The City’s show at Champion’s on Tuesday, August 27, Barone told Milwaukee Record about this show’s unique concept, memorable installments, dream guests, and why “locality is the backbone of longevity.”
Milwaukee Record: How did the idea for Milwaukey To The City come about? And can you explain the show’s concept?
Sam Barone: I was in my seventh year of standup and wanted to do more with comedy. Producing was always a route I admired, but after doing it for so long, I needed to distance myself from a Stand Up showcase—host, opener, feature, headliner—format. In reality, I was trying to figure out how to make Pee Wee’s Playhouse and Nickelodeon’s What Would You Do into a show that features people I like. Late night shows are nothing new, and their format is really simple. You’ve got three guests that pretty much carry the show and offer the viewer a look into the latest thing—whether that be a comedian, a movie star, or musicians. This allows me to have structure in the chaos I create! I also just love Milwaukee, and I think the stars of the city are the people who live here whether they be comedians, business owners, leaders, or musicians.
On Key City each guest shines in their own way. Comedians perform 10-minute sets then act as co-host for the evening. For each local business, we go and film for a day. I’ll either take a tour, learn about what they make or do, or even work myself. Then we premier the final cut on the show for the first time, and after the owners come on stage for their brief interview. After the business is the final guest, the musical act. They perform two songs with an interview in between them. I have the guests play games I made up to earn crafty trophies I made, and the business has a booth set up before, during, and after so that attendees can go learn about them and purchase anything they provide. I also make exclusive trading cards and stickers for each show. There are some dedicated fans that have most if not all of them.
MR: Why do you feel it’s important to highlight local comedians, musicians, and businesses in one show? Do you feel like there’s any overlap between those different areas?
SB: Locality is the backbone of longevity. It’s awesome seeing a known comedian from New York in our city, but the connection ends there. After the show, the only way to ever see those people again is either another show or online. Blurring the line between guest and audience by featuring people they can see in our city on the day-to-day establishes the connection I think most shows miss. That’s also where the overlap comes. It’s not necessarily with the acts themselves, but rather the audience that comes to see them. Fans of the band might’ve never heard of the comedian or business. Same with fans of the business not knowing the bands. At Key City, these audiences mix and mingle while maybe discovering something new they like. This opportunity isn’t always available at concerts, or showcases, or farmers markets. The attendees there usually already share common ground.
MR: As a comedian yourself, I know you have a lot of connections to local comedy, but how do you go about putting together a show? Is there thought to how all three elements will interact or do aspire to combine a random blend of local ingredients?
SB: It’s honestly all about timing and who gets back to me when. I reach out to local businesses first because I know how busy they are. These are people I’ve met at markets, expos, in person at their place of business, or through recommendations. Once most of the slots are filled, I’ll look at my list of favorite bands in the city. It’s very long and grows longer every day. I try to give them options based on what businesses would be a good match, but really it’s just whenever they’re available. I book the comedians last because I know most of them are available on a Tuesday night! I’ll give them options based on what kind of music they like. Some of them request shows where they’re huge fans of the band or business, which is always really cool to me. I like when they’re excited about who else is on because then I know they’ll be a great co-host.
MR: What have some of your favorite shows or guests been over the course of the show’s run, and why do they stand out to you? Have you encountered any surprisingly funny musicians or business owners?
SB: Chastity Washington was a blast. I made a game for her called “Chas Chas Revolution” where she had to make up dance moves based on phrases I invented. I’ve never smiled so much and the laughs were loud that night. I’m incredibly lucky to have any businesses on the show because it’s a very weird thing to agree to. My favorite has been Pete’s Pop’s. I respect Pete immensely for how he operates and gives back to the communities he’s in. It’s honestly something I aspire to be. Plus he brought free pops for everyone! I’ll definitely be having him back. Every performer has outshined expectations. I wanted to give a shout out to NilexNile. He’s been on the show twice, including filling in a very last-minute spot, and the professionalism he brings is off the charts. He’s charismatic and kind, and very dedicated to the city. He also genuinely loves being on the show. Him and Raegan Niemela are tied for most Key City Trophies!
MR: The show seems to have found a home at Champion’s. What makes this place most know as a sports bar and neighborhood tavern a great place for Milwaukey To The City to live?
SB: I have lived down the street from Champion’s for all of my time in Milwaukee. I’ve come to know the regulars, bartenders, and owners as family. So when Bobby saw me try and fail to get the show going at other venues, he offered what’s been the missing link this entire time: the backyard. It’s the perfect setting for how I want my show to feel. It’s cozy and familiar, but also transportive and engaging. When the sun sets on the stage it all feels so purposeful—even when it’s cold in September and October. Bobby lights up the fire pits and everyone enjoys some hot cocktails. You have to be there.
The show is traditionally an outdoor show that happens six times a year, but this year we’re experimenting with running it all year long with the help of Joey Turbo and Promises. We did four shows at the beginning of the year, and will finish at Promises for November and December’s shows. It’s been a lot of fun in a new environment, and being yearlong has helped build momentum with Key City.
MR: Can you talk about Tuesday’s show? What can people expect to see and experience?
SB: I’m very excited for Tuesday. Ryan and I have known each other for a long time, so it’ll feel more like a meeting of old friends instead of a formal interview. Julian Kegel is bringing in a bunch of Kegel Brau Centennial Lager four-packs that people can buy, and the video will actually be covering the Slow Roll happening Sunday. I’ve just finished the game Ladybird will be playing called “Short King Shuffle.” I’ve made small kings attached to hot wheels that they’ll have to roll to the end of the table without them falling off. The first 20 people in the door get a free exclusive trading card and sticker made by me.
MR: Do you have any dream comics, musicians or bands, and business owners for future installments?
SB: I’d love to have Mary Mack or Charlie Berens on the show. They’re not Milwaukeeans, sure, but I’d bend the rules. I just think they’d have the best time. Honestly the jobs I know nothing about are ones I’d be most excited to engage with: waste management, city planners, or MCTS would be great. I really want to have the Mayor on. I think Mr. Johnson would have fun, and it’d be a blast following him around. My dream bands are The Promise Ring and Misery Signals, so they’ll probably remain dreams. They were two bands that really helped form my musical identity and are important to me. Current artists that would be insane are Dinner Set Gang, REYNA, or Lakeyah. I’d make the stage a runway shape for Lakeyah because I know she’d own it! I like a lot of music, so when any performer I ask to be on the show says yes, I’m instantly stoked.
MR: Anything else you’d like to say?
SB: Milwaukey To The City started out as a dumb pun that was really hard to tell other people about because the spelling doesn’t translate verbally. Now it’s one of the coolest things I’ve ever done and I’m so excited to keep doing it forever. Public Access Television, here I come!
