Sad Boy Radio

Sad Boys For Real! Flawless Entertainment/Def Jam recording artist, Flex Sinatra, slides to PVTSTCK to discuss signing his recent deal, remaining a positive role model, how his childhood shaped him, and finding a new version of himself through every step of life. In the song, "Valuable," Flex Sinatra says, "You gotta give yourself forgiveness you can’t right every wrong,” Flex refle...

Sad Boys For Real! Owner of Classick studios, Chris Classick, slides to PVTSTCK to discuss managing Smino & Monte Booker, starting Classick studios, losing his mom at 18, and learning to let go of things that no longer serve a purpose. In the song, "End Of Youth," Ed Sheeran says, "Is this the ending of our youth when pain starts taking over? / I just don't know if I can eve...

Sad Boys For Real! Chicago artist, Daylight Tone, slides to PVTSTCK to discuss working with CB MIX, getting fired from apple, dealing with his anxiety, and running away from his past traumas. In the song "Still Yours," Big Sean says, "Sometimes you gotta break your heart to save your sould." Often, there's situations & people that it hurts us to let go of, but we need t...

Sad Boys For Real! Chicago DJ, Bae Wicked, slides to PVTSTCK to talk about being successful in a male dominated industry, finding herself as a person/mother after a nine-year relationship, prioritizing mental health, and the aftermath of her life-altering car accident. Big Sean said in the song, "Single Again," "I'm single again, blaming you is just so easy / But maybe the probl...

Sad Boys For Real! Chicago artist, KingTrey, slides to the studio to discuss his new album (The Southend Legend), being held at gunpoint as a kid, mental toll of living somewhere you’re “not accepted,” and the decisions that have made KingTrey who he is today. KingTrey says in his song “How Tony Became Trey,” “in 8th grade, them dudes came up & put a gun in my back / RIP TONY.” In this moment,...

Sad Boys For Real! Pivot Gang member, Mfn Melo, slides to the studio to discuss the formation of Pivot Gang, moving through life without his best friends, having a daughter, and the experiences that have shaped him into the Melo we see today. Ed Sheeran says in the song Tides, "I have grown up, I am a father now /Everything has changed, but I am still the same somehow." Throughout life,...

Sad Boys For Real! Chicago artist, SONNY, slides to the studio & discusses the inspiration behind his name change from hatesonny to SONNY, being forced to "accept" his reality due to where he grew up, and learning to make music based on real life experiences & how to grow through them. SONNY says in his song, "Trynna Heal," "Know all the mistakes I made just made m...

Sad Boys For Real! Chicago videographer, Rick Dawg, slides to the studio to discuss his "Vaulted Bars" series, the strain being a creative has placed on his relationships, and always feeling like there's a constant need to work Ed Sheeran says in the song "2step." "'Cause we're living life at a different pace, stuck in a constant race / Keep the pressure on, yo...

Sad Boys For Real! Pivot Gang Co-Founder, FRSH WATERS, slides to the studio to discuss starting Pivot Gang, being incarcerated early on, and how the losses of close family have impacted him both mentally & professionally. Frsh has faced adversity head on in many ways throughout his life; however, he's never been one to back down from the challenge. Instead, he's pivoted his life &...

Sad Boy For Real! Music video producer, Remi Momson, visits the studio to discuss working with No More Heroes, producing the video for "Point Me 2" by Fendi & Cardi B, and managing one of Chicago's hottest rappers Mello Buckz. Remi has stacked her resume in the entertainment industry; however, choosing this path didn't come easy. Remi quit her corporate job to pursue her drea...

Sad Boys For Real! Chicago rapper, Femdot., visits the studio to discuss his journey as not only an artist, but as a person. Femdot's projects are all connected to one another, and It's a concept that seems to follow Fem throughout everything he does. In this interview, we unpack the reasons behind why Femdot. is the person he is & the thing's he's learned about himself through...

Sad Boys For Real! Chicago artist, Ausar, slides to the studio to discuss his upcoming album, "I Now Know," and the experiences necessary to get to this point. Ausar has had traction behind his name since his first drop; however, with that traction comes unrealistic expectations that take a mental toll. Through this, he's had to navigate failed label deals, relationships, and even a...

Sad Boys For Real! Chicago bartender, Bowtender, slides to the studio to discuss starting his own business (Dat Slush), breaking up his family, healing his inability to love, and separating his persona from the actual person. Drake says in Karaoke, "I know they say the first love is the sweetest/ But that first cut is the deepest," This concept often rings true for anyone who has experie...

Sad Boys For Real! Chicago rapper, Kayo, slides to the studio & discusses the moments that helped him create his debut album, "It Was fun While It Lasted." Kayo uses this album to journal not only the highs in life, but the lows as well. From having a video shot by Cole Bennett, to his volatile battle with depression, losing the girl of his dreams, and having business ruin close fami...

Sad Boys For Real! Chicago DJ, Dj Enigma, slides to the studio & discusses the moments that have helped make him a staple in Chicago. From being Sicko Mobb's official DJ to opening for artists like Future, Enigma has established his name in not only Chicago, but across the US by creating his own lane & not being scared to take risks. In the song "Monster," Justin Bieber sings...

Sad Boys For Real! Atlanta artist, Trub, comes through & discusses his recent single with Project Pat hitting 3 million views, working with Juicy J, his struggles with anxiety, and the fear of the things he'll be missing being 100 percent locked in on music. In the song, "Rich," August Alsina sings, "Am I wrong for wanting better / Should I just settle forever? / Ooh, I swea...

Sad Boys For Real! Chicago Rapper, Arigon, comes to the studio to discuss his new album (F.H.L) & the experiences that helped him form this new body of work. From facing unresolved trauma, to understanding coping mechanisms, and finding alternative ways to change after a medical diagnosis. The most significant being giving up alcohol. Arigon says in his new song "Drowning," "Fee...

Sad Boys For Real! Chicago artist, Saint Millie, visits the studio to discuss his days helping build Jugrnaut, being a member of Treated Crew, and his transition from being a full-time artist to being a full time artist manager. Millie established himself as a disruptor within the industry & helped establish a culture for Chicago music. Bringing together the sounds of old Chicago & new Chi...

Sad Boys For Real! Chicago DJ, Yaya The Base, slides through the studio after opening her first residency (Club Yaya). Yaya & I discuss her inspiration to pursue neuroscience and Doing; as well as, the traumas that have impacted her everyday since she was a child. From loss of loved ones to toxic patterns within relationships. Ed Sheeran says in the song Runaway, "I've never seen my d...

Sad Boys For Real! Chicago Rapper, OG Denzo, slides to the studio & discusses his new outlook on life since leaving prison. Denzo has been featured on IHeartRadio & collaborated with countless Chicago rappers, OG Stevo being one of them; however, it all came to a halt when he had to serve 3 months in prison... Denzo reflects on his experience in prison & discusses the impact it's h...

Sad Boys For Real! Chicago DJ, Gato The DJ, visits the studio to discuss his early success as a DJ, DJing for artists such as Miky Woodz & El Alfa; however, this early success leads to self-doubt when hard times come along. There have been many ups & downs in the industry for Gato (COVID being a huge one). Being a part of night life brings a high in of itself; however, when everything is d...

Sad Boys For Real! For our 100th episode we have Chicago DJ, Simmy, slide through the studio to discuss her journey as a creative. More importantly, we discuss the lessons she's learned through being a DJ, producer, entrepreneur, and more importantly a human. As creatives, we're doubted & viewed as selfish due to the unique lifestyle we choose to live. Our job is more often viewed as a hobby r...

Sad Boys For Real! Miami DJ, DJ PEEWEE, slides to Chicago to discuss her 10 year career & the events that have shaped her into the woman she is today. PEEWEE has played at Coachella, Rolling Loud, and even Paris; however, it's the things that happened behind the scenes that have had the biggest impact. PEEWEE has faced countless hardships throughout life that made her question, "why was I put...

Sad Boys For Real! No More Heroes A&R, Danielle Casel, slides to the studio to discuss her transition from teaching into the music industry, working with top acts such as Fly Nari, OG Stevo & DCG Bros, and the way in which her mental health struggles have continuously impacted her. Hailey Williams sings in the song Fake Happy, "I been doing a good job of / makin' 'em think / I'm quite alri...

Sad Boys For Real! Two years later & we're still at it! We invite former guest & close friend Equan back to discuss the journey throughout the past year. This year taught us the value of our time on this earth, but also refocused us on the importance of treasuring the people around us. Over the two years we've talked to the biggest artists in Chicago about their mental & personal strug...