Sam Barone Joins Local Comedians for ‘Cowboy Killers’

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Photo via Cactus Club

Sam Barone

Sam Barone

For Sam Barone, comedy became a route to finding himself. 

“When I was in my early twenties, I was very lost. I had all these ideas for who ‘Sam Barone’ would become, but no clue which paths would take me there,” the native Milwaukeean relates. After trying out bartending, filmmaking and music as vehicles for expression and identity, comedy became arose as an option in a somewhat typical way. 

“A classmate told me about an open mic, and I entered stand-up comedy the same way I did anything else; clueless and stumbling,” Barone admits.  But stinking at stand-up his first time wasn’t the stumbling block it was with his previous endeavors “because it was so easy to see the path to getting better. It was exhilarating, and I think helped me overcome a fear that set most comedians back. I'll say that I've never felt shame in being bad at comedy like I did in anything else I tried.” 

Barone will shamelessly join a bevy of other mostly local comedians on Wednesday May 1, 8 p.m. at Cactus Club for “Cowboy Killers: A Comedy Show.” He won’t speak for the other comics on the bill—headliner Rachel Mac, Erin Morris, host Raegan Nimiela and Ann Arbor’s Andrew Yang—but as for his act being appropriate for a show by that title, he says, “I hope to bring a certain tenacity to the stage that represents what it would feel like watching two men shoot each other on a dusty road. In all seriousness I’m a city kid through and through. Any time I wear cowboy boots, it feels like cultural appropriation.” 

10 Tenacious Years

The tenacity of which Barone, a who celebrates 10 years in stand-up in 2014, speaks, however, has been channeled in a direction where he shares the comedic heavy lifting. 

“The tough thing about comedy is that you’re constantly selling yourself as the product and I was growing increasingly tired of doing so,” Barone says to preface his resolution by stating his plight. “I wanted to create something for others that was still an authentic piece of myself, but not the whole thing. A variety show was the perfect structure. It allowed me to do all of the things I loved without screaming 'ME ME ME!”'

Barone’s variety show, “Milwaukey to the City,” has a hometown-boosting concept to match its clever name: Milwaukee comedy, music and business. 

“I knew I wanted a comedian and musical act to entertain the audience. Next was a guest they could engage with,” Barone asserts of the revue he began at Champion’s Pub in 2022 and now alternates with Promises Bar. “That’s where the business came into play. Having them set up shop at the show would provide a face-to-face greeting with the audience, and they could sell during the show to expand their customer base. The video portion naturally came with that. I knew the audience would love seeing how the business operates. Being a ‘reporter on the scene’ gave me the opportunity to naturally premier that video.” 

In the Moment

Because Barone insists “Milwaukey” is meant to be experienced in the moment, “there is no plan to have it fully online anytime soon.” However, anyone wanting to see the show vicariously before taking it in live can go to social media. “Thanks to my new co-producer, Manny Zander, we record each show, but mainly use the footage for promotion. If you’d like to see these, and all the videos from past businesses, you can visit the ‘Milwaukey to the City’ YouTube and Instagram pages!"

Of his fellow Cream City Killers, he says, “Rachel Mac’s charm and inviting presence are the perfect front for her wonderfully aggressive comedy. She has this insane talent of casually telling jokes, seemingly unrelated, so that each callback is met with surprised, a rupture of laughter. Rachel is one of my favorite comedians. 

“I’ve had the pleasure of first meeting Erin Morris when I moved back in 2019. The hard work she has put in since then is outmatched only by her writing. Even when workshopping, I love the sharpness of her wit. It always comes together with a lot of confidence and great timing.” And of his extra special affection for Niemela, he confides, “Raegan is my best friend in this scene. It is through her immense support that all of us in the scene feel seen. There isn't a single person I could name that would be more of a friend to you than Ms. Raegan Niemela. I'm incredibly grateful for her.” 

And as someone who has also spent time in Chicago honing his act, Barone shares of Milwaukee’s comedy scene, “I think it’s cool to be a part of the growing community.” 

If comedy gives him a sense of community, Baron says that “Milwaukey to the City” provides him the even more existentially vital quality of purpose. “I feel so authentically me when producing this show,” he continues. “I said before that I've never felt shame as a comedian, but I have felt it as a person. I spent a lot of time not liking who I was. Stand-up was only a step away from that feeling, for a max of 30 minutes a gig. Every hour I'm editing the business’ video, every minute I spend crafting props, and every second it takes me to write out each ‘City’ script is time I finally feel like I'm who I'm supposed to be. 

What Barone says about seeing a Chicago Blackhawks game should give prospective “Cowboy” attendees a taste of what he's about...

Comedy Mount Rushmore

A new, occasional addendum to Shepherd Express comedy coverage is Comedy Mount Rushmore, where local funny people speak of four figures that were important in the development of their sense of humor whose likenesses they would like to see carved in a rock formation like a quartet of presidents ... or whatever!

Describing his Rushmore subjects in this opening installment is No Tell Comedy Milwaukee organizer and comic in his own right Judd Reminger, who keeps his choices Milwaukeean:

Chastity Washington is the funniest person in Milwaukee. There isn't anyone that has seen her that didn't love her. She is the strongest comic voice in the scene. Has been for about 20 years. 

Matt Kemple is the brains behind Milwaukee Comedy LLC. They have been putting on shows for over 15 years in comedy. 

Chris Barnes is the comedy godfather of Milwaukee. I got introduced to him a few years ago, but he has been doing it for 30-40 years. He could tell you what it was like to be doing comedy back in the day and kills on stage every time. 

 AJ Grill, one of the comedians I have seen grow and raise the stakes for everyone in the comedy scene. He is heartfelt, loves comedy and pushes to be the best comedian he can be. 

Since Barnes has never been featured here yet, here he is hilariously, if profanely, describing an encounter with an amputee Target employee...