How Sad Boy Saturday Became Milwaukee’s Hottest Alternative Dance Party

Once a month, Milwaukeeans spend their evening singing, dancing and partying with the “Sultan of Sadness.”

Despite the name, Sad Boy Saturday is a ton of fun – and its journey to becoming a night-out staple was a complete accident. 

Five years ago, co-founder and promoter Brian Radmond was tending bar in Bay View, looking for a way to attract more customers – and more tips. So he brought in his friend Sammie K Anderson to DJ. After a few sets, a customer gave the event its name and Anderson became known as the “Sultan of Sadness” or “Emperor of Empathy.” 



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“It blew up,” Radmond says. “We had this small bar completely packed after the second event, so we had to move to a bigger bar and then a bigger bar and now it is kind of the event that it is.” 

And that event is perhaps Milwaukee’s most popular alternative dance night, held once a month, frequently at The Miramar Theatre, but also rotating through X-Ray Arcade and other local venues. Anderson spins emo hits – and some deep cuts – from the ’90s and early 2000s, including plenty of My Chemical Romance and Fall Out Boy, and he always closes the night out with Weezer’s “Say It Ain’t So.” 

“It’s just a lot of fun to come as you are, have some drinks and sing along with your friends,” Radmond says. Five dollars and a 21+ ID will get you in the door. This month’s event will be on Aug. 27 at X-Ray Arcade.


This story is part of Milwaukee Magazine‘s August issue.

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Alli Watters is the digital and culture editor at Milwaukee Magazine. That means that in addition to running this website, she covers art, entertainment, style, home and more for the magazine. It also means she doesn't sleep much.