Ishmael IshDARR Ali

Milwaukee Rapper IshDARR Talks Music, What It’s Like to Work with Matthew McConaughey

He may already be the greatest Milwaukee musician of his generation, and he seems to be gunning for the title of “best actor” too.

Since its release last week, the gritty crime drama White Boy Rick has raked in more than $11 million. The film – which follows the real-life exploits of America’s youngest FBI informant – is set in Detroit, but it has a surprising Milwaukee connection too. Namely, Brew City’s own Ishmael “IshDARR” Ali.

When he was still in his teens, IshDARR had already become one of Milwaukee’s most accomplished hip-hop musicians. Now 22, he’s played to packed houses around the country, and his songs have generated millions of streams on Soundcloud. And he may be as good at acting as he is at rapping, if his recent star turn in White Boy Rick is any indication.

We recently chatted with Ali about his Milwaukee roots and his recent success.

Ishmael IshDARR Ali

How did you break into the Milwaukee music scene?

I’d been been writing music since seventh or eighth grade but started taking it more seriously my junior year of high school. I recorded my first song by myself – it was called “First” – and put it out there. I wasn’t expecting much of a response from it, but people really liked it.

Did you start playing shows around town pretty soon after that?

Yeah, I started playing at The Miramar. The Rave was bringing in some pretty dope hip-hop acts at the time too, and I was able to open for a few of them. Nothing too crazy, though – it’s not like I dropped the single and The Rave started calling me directly. A lot of school friends came out to those early shows. They wanted to support me.

A lot of the concert venues in the city are 21+ venues. Was that a barrier for you early on, as a teenage performer?

Absolutely. When I started to perform I was 16, and you have to be 18 to get into most venues, so that was something we had to work around. We made our own venues, in a sense, and put on shows in art galleries, basements, barber shops – wherever we could find an all-ages space.

The actress Chloë Grace Moretz retweeted one of your songs in 2015, and hundreds of thousands of new fans found your music almost immediately after. Tell us a bit about that.

We’d just dropped Old School, Young Spirit. And Chloë tweeted that she liked one of the songs, “Too Bad.” I wasn’t sure who she was initially, to be honest, but when my manager started naming some of the films she’d been in, I was like “Oh, that Chloë.” She helped boost the track to No. 1 on the Hype Machine charts. I’d never charted anywhere before that, and all of a sudden I was No. 1.

Did you start to attract more fans outside the Milwaukee area then?

Yeah, the fan base became nationwide around then. I started seeing people in different states – and different countries – liking the tracks.

That’s when I saw a door open for me, and I immediately told my mom and dad. They’d wanted me to go to college – I was on the honor roll at Messmer High School, and I’d just thought of music as a hobby. But I started to think that maybe I had something special with it, and I got my parents to see that too, and to trust me to work on it full-time.

How you were cast in White Boy Rick?

My manager told me there was a casting call that I might be interested in. I was like, “I guess I’ll take a look at it.” When I sat down to read the script, and found out that it was based on a true story, I started to really like it.

They sent me two scenes to read. I rehearsed for about four or five hours, self-taped the scenes and sent them back the same night. About two weeks later, the director told me he loved the tape and wanted me to come into Los Angeles for an audition. I jumped on a flight the next day and got good vibes from everyone at the studio.

Seven months later, I was on tour, in Dallas, about to go on stage, and my manager told me that I had to check my email right away – I found out they were offering me the role.

What was the production process like?

The film wasn’t shot in Detroit, even though it’s set there. It was mostly shot in Cleveland, for tax reasons. So the day after my tour ended I flew to Cleveland and spent seven weeks there shooting the film.

Filming the movie has been the best experience of my career so far. I did plays in high school, but I fell in love with acting on that set.

What was working with Matthew McConaughey like?

It was great – my mom and aunties went crazy when they found out he was in the movie.

I met him my second or third day on set, in the makeup room. I told him I’d be playing Freaky Steve, and he was like “Okay, okay, looks like we’re going to be doing some business together, Freaky Steve.”

Half the time I couldn’t tell when he was acting. I’d think we were having a real conversation, and then the director would shout “cut,” and I’d find out that Matthew had been in character the entire time. I learned so much from him – he was a great mentor.

What’s next for you?

I do have a project about to roll out. There’s no date on it just yet, but it’s definitely coming out this year. And I’ll be announcing a tour with a dope artist in October too.

And then it’s going to be relax mode for a while. I’m going to go back into the studio, but I’m going to relax a little first.




Lindsey Anderson covers culture for Milwaukee Magazine. Before joining the MilMag team she worked as an editor at the Museum of Contemporary Art Chicago and wrote freelance articles for ArtSlant and Eater.