Rising Rapper IshDARR Talks Milwaukee Roots & Acting Alongside Matthew McConaughey in Upcoming Movie 'White Boy Rick'

Weston Rich


"There's more to Milwaukee than what a lot of my friends are used to and what a lot of people see."

For years Milwaukee was barely in the conversation when it came to notorious rap cities. Now, despite being overshadowed by the likes of New York, Atlanta, Los Angeles and Chicago, Milwaukee is finally stepping into the hip-hop ring thanks to IshDARR. 

Since 2015, the 20-year-old MC born Ishmael Ali has been carving a lane for his hometown, starting with his breakthrough track "Remember." His penchant for addictive hooks continued with the release of "Too Bad" later that summer. In 2016, IshDARR punctuated his efforts with his project Broken Hearts and Bankrolls, highlighted by his growth on the mic and seamless beat selection, ultimately gaining a legion of fans. 

This year, IshDARR's main focus has been solidifying his place as the face of Milwaukee. He first gifted fans his six-track EP titled Four the Better. To keep the momentum going, he shot the video for his 2016 track "Dumb Playing" center court at the BMO Bradley Harris Center, home of the Milwaukee Bucks. IshDARR then landed a movie role for the drug crime film, White Boy Rick, starring Matthew McConaughey. For the cherry on top, the burgeoning rap star will perform at his city's Summerfest 50 in July alongside Future, Big Sean, Migos, Alessia Cara and more. 

Billboard recently spoke to IshDARR about his childhood in Milwaukee, working with McConaughey on White Boy Rick and his desire to become the face of his city. 

Your record "Dumb Playing" has been getting a lot of feedback, especially from basketball lovers. 

Ah, man. I'm so glad to hear that, especially from the hoopers. That was definitely the goal -- to touch some souls. It touched the hoopers' hearts a little even more than I even expected it to. I'm so glad it can do that. 

How did it feel to shoot the video at the BMO Bradley Harris Center where the Milwaukee Bucks play? 

Man, that was definitely the craziest freaking day I can say for a video shoot -- ever. I've been in Milwaukee my whole freaking life, so seeing that court and just seeing the cats playing on there, never thinking that I'd be on the court, it was definitely an emotional rush. It felt good, though. I've been seeing this floor and seeing this arena for awhile, but I had never made that next step to be center court or moving towards something more. To just be there, it was definitely on some dream-come-true shit.

Considering Milwaukee is a small rap market, who did you gravitate to as a kid growing up musically in hip-hop? 

Growing up, I was gravitating towards mostly what I was hearing. My dad used to play the old hip-hop. He was a DJ. He was really into the old Boogie Monsters. He was playing A Tribe Called Quest, De La Soul and all types of stuff. To me, it was cool but it wasn't taking me there or nothing. I was small and shit but as I got older, the music was a continuous thing and it kinda grew on me. That's kinda how my initial groove came -- just hearing that. Then I started to discover artists on my own. That era was back when [Lil Wayne] was heating up. This was mixtape Wayne season. It was a mix of what my pops played when I was growing up and [then with me] just seeing what Wayne was doing at the time. The whole Young Money [movement]. Kendrick [was another]. It was inspirational seeing how those cats were moving. That's initially what motivated me to put it on wax and put it on paper. Once I tried it, that was it. 

You have a line on "Dumb Playing" that goes, "Switched my career and told mama I'm gon' innovate." What was your parents' reaction to you deciding to pursue rap full-time? 

With that line, that actually goes for both mom and pops. I definitely did tell moms more because it definitely took me talking to her a little bit more to understand than pops. Before the music, I was doing football, actually. That's what pops knew. That's how pops raised me. Moms knew that I was into football. So, before the music, that was it. I was No. 32. I was a running back and I was real good on the field, but it was all pre-high school. The whole first seven or eight years, I was just on the field. I was playing football and that was all that I wanted to do. That was the dream. It was sports, sports, sports. I didn't really see nothing else. I was young and I was like, I'm gonna take this football shit all the way. Things didn't really keep going that way the older I got. [Then] my passion for music drifted over a bit and I kind of let go of the football dream. 

I was like, "Moms, I got a different passion with this music shit." I found it more so when I did it in high school. I noticed that I wanted to take it more serious. She couldn't do nothing but be supportive, which she definitely was. It took her some time because her whole thing was like, "If you do it, I just don't want you talking about nothing." I had too much instilled in me for that to be a worry, but that was always a concern of hers so I always keep that in the back of my mind. 

You recently were casted for a movie starring Matthew McConaughey titled White Boy Rick. Do you have a favorite moment or memory from shooting with him so far? 

It's just everyday that we're with Matt, there's a freakin' favorite memory because he's like the dad. He's White Boy Rick's dad. He's out shooting a lot with White Boy Rick and I'm in White Boy Rick's crew, so we don't see Matthew too much, but we shot with him probably about five times. Every time, he always comes up to the whole crew, talks with us, tells jokes and he's so freaking cool. Just his vibe's off top, I didn't think he was going to be so normal and so chill. Everybody on set is like, "Yup. That's OG Matt." He always made sure to introduce himself to the cast and everybody he could. It's so chill on set. Definitely the craziest life experience in my 20 years of living.

With you currently dabbling in acting and rapping, is that a long-term plan of yours to tackle both?

That's definitely the plan more so moving forward, just because I did do some acting back in high school. I was doing some school plays. That's how I originally started in acting. I did all the school plays for four years. Then I left and the music shit took off. When the movie role for the audition came back in, I was like, "Oh shit. Let me try it." It's definitely been a little minute, but I know since I left, I always wanted to do acting. I'm gonna keep doing it. My pops was really a fan of it. He was like, "Yo son. I know you're doing music, but before I'm gone, I want you to either be on Broadway doing a play again, or I want to see you on the big screen."

It was just literally the craziest shit, because two or three weeks after he said that, the audition [for White Boy Rick] came through. I was like, "Damn, it would actually be crazy if we get this and I'd tell pops." It was just like the timing was crazy. So, after this, the goal is to definitely keep the acting up just because it's another passion that I found early on. 

How do you ultimately plan on becoming the face of Milwaukee? 

For one, I think it's just giving everyone in the city that initial hope and that there's more to Milwaukee than what a lot of my friends are used to and what a lot of people see. So doing things like this, is drastic for the city. 

Everybody is looking like, "Yo. The wheels are turning." We got the Milwaukee Bucks heating up. We made the playoffs this year. Music-wise, people are coming to respect the grind more and respect the music as a whole. [It's] not even [about being] the face -- because that's gonna come long-term -- but more so be the voice for now for the youth. I'm in a mode where I'm like, "Let's turn up now and be the voice for the whole city." That's just more time, more actions and keeping the ball rolling. I got some more things planned for the city. It's all about keeping things in motion. Nothing is getting stagnant. I feel like with that, the city is appreciating and knowing that this cat is doing something inspiring. Milwaukee is my baby.