Flagship · LiveGentlemen's Night
Three hours built for the after-hours crowd. The rock that runs Chicago, the new noise breaking right now, and the stories that only happen after the streetlights come on.

Proud SAG-AFTRA MemberChicago DJ, radio host, producer, and event specialist — The Master Podcaster. Host of Gentlemen's Night on Rock 95.5 / WCHI-FM. Over a decade in the booth, seven years inside iHeartRadio, now headlining Saturday nights in the third largest market in America.
Flagship · LiveThree hours built for the after-hours crowd. The rock that runs Chicago, the new noise breaking right now, and the stories that only happen after the streetlights come on.
iHeart Radio ExclusiveAn iHeartRadio exclusive — only available on iHeart. Extended interviews, behind-the-board breakdowns, and the conversations that don't fit a radio clock.
Studio + NightlifeTen-plus years of nightlife in one feed. Recorded live from Chicago's best rooms — full DJ sets, no edits, no skips. The floor energy mixed for headphones.
You got a shoutout, a wild story, a song request, a confession, or something Chicago needs to hear? Tap the mic and talk to Steve Stylez.

Steve Stylez is one of Chicago's voices for radio, podcasting, DJ culture, and real entertainment. Born in California and raised between Jefferson Park on the northwest side of Chicago, Des Plaines, and Rockford, Illinois, Steve's story is pure Midwest Hustle with a little California in the DNA.
Before the radio mic, before the big stages, before the interviews and podcasts, Steve was just a kid who loved music. By high school he was the type to be in the kitchen late at night, headphones on, practicing DJ sets and making beats while everybody else was asleep. No fancy setup. No big co-sign. Just passion, patience, and a whole lot of trial and error.
Self-taught from the ground up, Steve started DJing small house parties, weddings, and wherever somebody needed music. From there, he worked his way into the nightclub scene and eventually became known as one of the Midwest's Premier Gentlemen's Club DJs, working 10 clubs in 10 years. That era taught him how to control a room, read energy fast, keep people entertained, and move a crowd without forcing it.
But Steve's background goes deeper than just DJing. He is also a songwriter, producer, recording engineer, and musician by trade. He can play 13 instruments, reads sheet music, understands sound from the inside out, and brings that same ear into everything he does — whether he is producing audio, hosting a show, building a new show, sales, or creating content.
Before fully stepping into radio and entertainment, Steve also worked as a high school Special Education teacher and music educator. That chapter gave him patience, leadership, communication skills, and the ability to connect with people from all different walks of life — something that still shows up in his work today.
Steve's musical taste is all over the map in the best way possible. As a teenager, he was blasting Linkin Park's Hybrid Theory on a CD player, while also being shaped by Breaking Benjamin, Hinder, The Offspring, Nipsey Hussle, Dave East, J. Cole, Eminem, Central Cee, and everything in between. Rock, rap, pain music, hype music, storytelling — if it has feeling, Steve is locked in.
Now, Steve Stylez brings all of that life experience into radio, podcasting, DJing, live events, and digital media. His style is Chicago, his energy is real, and his voice comes from actually living the stories he tells.
Steve is also a proud member of SAG-AFTRA, the union representing professional broadcasters, recording artists, and media talent.
Outside the booth, Steve is a lifelong swimmer, Funko Pop collector, diehard White Sox fan, Dragon Ball Z nerd, mafia movie fan, chef, tattoo lover, anime watcher, baseball guy, basketball fan, and most importantly, a proud father making memories with his son.
"Being persistent got me here. Staying consistent will keep me here."
Every show goes to podcast. Full episodes, extended cuts, in-studio interviews, and the mixcloud sets — wherever you listen.
The Saturday night show, on demand. Full episodes the morning after they air.
Powerful conversations, controversial questions, news and entertainment — live from Chicago.
The throwback cuts and the stories behind them. Hip-hop, rock, and the eras that built the city.
Unfiltered takes on culture, music, and the work it actually takes to stay in the booth.
An iHeartRadio exclusive — only available on iHeart. Extended interviews and the conversations that don't fit a radio clock.
Full DJ set, no edits, no skips. The Saturday energy in headphone form.
Got something funny, wild, random, or real to say? Text me.
I read text messages on the radio Saturday nights. Got a topic? Text me. Want to request a song for me to play? Text me. Want a shout-out on the air? Text me.
Rep the movement. Limited drops, exclusive designs — built for the city that raised the sound.
For bookings, brand partnerships, podcast inquiries, DJ requests, radio opportunities, or business questions, fill this out and Steve Stylez's team will follow up.