Milwaukee rappers start a new verse with film roles
Ish DARR is used to dancing on stage, but at the moment, he’s dancing in an alley. ❚ The 22-year-old Milwaukee rapper, born Ishmael Ali, is in Black Cat Alley on the east side, posing for a Journal Sentinel photographer, when he checks his Instagram and starts cheering. ❚ The poster for a new movie starring Matthew McConaughey, “White Boy Rick,” has just been released — and Ish DARR himself is on there, right in front of the Oscar winner. ❚ Wide-eyed and cheering beside Ish DARR, arm wrapped around his shoulder, is Isaiah Ali, 23, known in the Milwaukee hip-hop scene as Boodah DARR. Boodah DARR is excited for his brother, but he’s also excited for himself: He has a role in “Rick” too. ❚ On Sept. 14, they’ll be on movie screens all over the country. ❚ “I think they’re incredibly talented and can do anything they put their minds too,” said “White Boy Rick” director Yann Demange. “Maybe they will be renaissance men. Both of them can be.”
Countless actors across the country are hustling to get the kind of roles the Ali brothers got in “Rick.” But they landed the parts without any major acting experience.
Ishmael’s only acting experience was supporting roles in plays at Messmer High School, where he also developed his skills as a rapper. Hip-hop site The Source shared one of his songs when he was just a senior in high school, and the following spring his single “Too Bad,” off the “Old Soul Young Spirit” mixtape, went viral. As of this week, he has more than 22 million streams for his songs on Spotify alone, along with millions of streams on Sound Cloud and YouTube.
His older brother Isaiah was a major influence on Ishmael’s hip-hop aspirations, and has started to make some waves with his own projects, amassing more than 600,000 Sound Cloud and Spotify streams.
The move to movies
So how did the brothers make the leap to the movies?
In late 2016, Ish DARR’s booking agent at the time at William Morris Endeavor got notice of a casting call for “White Boy Rick,” based on the true story of Richard Wershe Jr., a Detroit teen who was an undercover agent for the FBI in the ‘80s during the height of the country’s crack epidemic — and was in prison from 1988 until his parole last year on a drug conviction. (Wershe is in a Florida prison serving time for pleading guilty to his involvement in a car theft operation.)
Ishmael sent an audition video, and a little over a week later, was flown out to Los Angeles to audition for Demange in person.
In early 2017, he was about to take the stage at the House of Blues in Dallas when his manager told him to check his email.
He had landed the part of “Freaky Steve” Roussell, who in real life was allegedly one of Wershe Jr.’s right-hand men.
“My mind was blown. It was just too much,” Ishmael said about getting the news. “It was a surprise because I had never done any acting before except for high school.”
But that didn’t concern Demange; the actor playing “White Boy Rick,” Richie Merritt, didn’t have any experience either.
“You’re looking for who is going to bring authenticity to the moment, rather than casting an actor who is going to try and be transformative,” Demange said. “I met a lot of actors for the part and, in the end, I thought Ish DARR had a wonderful quality that was unique. He knows the world, but he’s not your typical macho guy. There’s a sensitivity to him, but he’s also funny, and that was important.”
‘Really in his own lane’
Ishmael was on set for six to seven weeks from May through June 2017, then spent a week filming in Las Vegas.
“How I would describe my character is he’s really in his own lane,” Ishmael said. “He doesn’t really care what nobody says. He’s going to do him regardless.”
“I thought it would be intimidating,” Ishmael said of filming. “Maybe the first few days, the first week, I didn’t want to say too much and just learn the environment. … It wasn’t as intense as I thought it was going to be. … It was really easy to learn quickly.”
Demange said he fit right in.
“I love the kid,” he said. “He was a very talented all-around artist with a big future and a lovely kid to work with. He’s a really focused, hard-working professional, has got great values and a nice work ethic.”
About a few weeks into the filming, Isaiah took a Greyhound to Cleveland to “kick it with him (Ishmael), see how the movie life was going, big brother duties.”
The next day, Isaiah went with his brother to a cast and crew party, and met with one of the producers who was casting for an open role. The producer encouraged Isaiah to try out.
He shot an audition tape, and a few days later, “she was like, ‘Guess what? He loves you, he loves your face. You got the part,’ “Isaiah said.
His commitment lasted a few weeks. “I’m the funny guy in the family, so this was kind of natural for me,” Isaiah said. “I wasn’t really nervous, to be honest. I was just being me on a larger scale.”
Connecting with McConaughey
The brothers got some guidance from seasoned actor RJ Cyler, who took them under his wing; he plays Wershe associate Rudell “Boo” Curry in the film, a role Ishmael originally read for. Cyler starred in last year’s “Power Rangers” reboot and the acclaimed indie “Me and Earl and the Dying Girl” in 2015.
The brothers also got to rub elbows with fellow rappers and actors YG and Danny Brown. And yes, they got to act with McConaughey.
“He is the real deal,” Isaiah said. “He was talking with us, and I felt like we were having a personal connection; he was getting ready for a scene and warming up. I was like, ‘This is crazy. I’m actually talking to Matthew McConaughey.’ “
This past Friday, the Ali brothers were to be with McConaughey and several cast and crew members again for the international premiere of “White Boy Rick” at the Toronto International Film Festival.
On Monday, the brothers plan to attend a private screening of “Rick” in Milwaukee, and will be in Detroit for a screening later this week.
Music will continue to be a focus. Ishmael is working on a new Ish DARR album and planning a show for later this year, while Isaiah’s latest Boodah DARR project is planned for early next year.
But they’re hoping for more acting roles, too, and are meeting with agents who can help them get parts.
“It opened up a whole new set of dreams,” Ishmael said.