No matter where you live in this country, race is a sensitive subject. When you live in city many are quick to remind is among the nation’s most segregated, the oft-referenced racial divide becomes even more evident. Milwaukee’s undeniable geographic boundaries have also played a part in forging a divide in local comedy that—while not at all exclusive to this city—finds only a handful of comedians performing to both “urban” and “mainstream” crowds. Let’s just call them what they are: black and white audiences. Still, a select few Milwaukee comics have taken it upon themselves to bring their material to both settings, as unfamiliar and occasionally uncomfortable as one particular type of venue may be to them.

Ton Johnson (pictured, left) and Caste Of Killers co-founder Jason Hillman (right) are two such comedians. They were kind enough to come to Milwaukee Record HQ to discuss their experiences performing in each setting, how black and white rooms differ, and why there isn’t more overlap between the city’s two stand-up scenes. Despite the heavy subject matter, Johnson and Hillman manage to pepper in some hilarious tales of triumph, cringing recollections of bombing, and an overriding hope the line between urban and mainstream comedians will continue to blur. See Hillman perform Thursday during the Milwaukee Comedy Festival. You can catch Johnson at Nick’s House on August 15.

As always, this episode is brought to you by our friends at Ale Asylum, which was enjoyed on air, and 42 Ale House/42 Lounge. Music in this episode comes courtesy of Surgeons In Heat (“You Never Know”) and Group Of The Altos (“Fucks With Us”). Subscribe to On The Record via iTunes or Stitcher (for free!)