All the odds were against Longshot.
It was 1986 and the little boy then known as Chad Heslup was living in a hotel room in North Oakland. The eldest of six siblings by four different fathers, Heslup was responsible for feeding his brothers and his sister powdered milk, cold cuts, and bread before getting them to school. Then he hit the streets to panhandle. If he made enough money, he’d buy his “dope-sick” mother a pack of cigarettes.
“The images and memories I have in my head, no kid should be around that,” the Minneapolis rapper says of his childhood. “I saw a lot of stuff: mom smokin’ heroin, crackheads comin’ in and out, being interviewed by police.”
Heslup’s grandmother back in Chicago arranged for the family to come home. But when his mother ended up in the hospital, leaving all six kids with a babysitter for over two weeks, the sitter called the Department of Children and Family Services of Illinois. Heslup and his siblings were torn apart and dispersed to different foster homes. He spent three years with his estranged father’s then-wife and a year with his grandmother.
On the day the kids were to be returned to their mother, Heslup saw her slap a caseworker in court and get arrested. He knew then that the family would never reunite. He landed in a group home run by Boys Hope Girls Hope. Thanks to scholarships, he attended Catholic middle school and high school, escaping into baseball and football. His athletic talents got him into Drake University, where an injury ended his football career during freshman year.
Heslup didn’t leave school empty-handed, though; Drake is where he learned to freestyle. His teammates often rapped together, but Heslup didn’t join them because he didn’t think he was good enough. “Now, looking back, they all sucked,” he says. “But in that time, they were all so dope.”
After a teammate’s friend, a guy from the Twin Cities, “killed” one night, Heslup went back to his dorm room, put on track 18 of the Roots’ Illadelph Halflife, and rapped all night. That sealed his fate. He left Drake, moved back to Chicago, and at age 20, he performed for the first time. The exhilaration onstage was greater than anything he’d felt playing sports. “I knew the first time I performed that this was my life’s calling, not just something I wanted to do,” he says.
Unable to participate in Chicago’s open mics because of his age, Longshot relocated to Washington, D.C. to “pay my rap dues,” he says. He slept on the couch of a friend’s studio, wrote all day, and recorded at night. His first 12-inch, Happiness Is Hard to Find, dropped in 2002.
Longshot’s albums now number nine, the same amount of years he’s lived in Minneapolis, where he relocated to “soak up as much game as I possibly could” from the local hip-hop scene. He shares credit for his latest LP, Parades, with Doomtree producer Lazerbeak. Over funky, innovative beats, Longshot shares his dreams for a happy home life, emerging from poverty, and building a sustainable music career.
The title track pays homage to people of color killed by police who don’t get “no damn parades,” while other cuts cover topics such as girls in the club (“Holla”), drugs (“Narcotic”), and contemptible men (“Let Him Go”). Ultimately, Longshot arrives at a hopeful place on “True Story”: “I want to live without police harassment/I want to live in peace and happiness/I want to live where my son feels safe and my daughter gonna grow/And if you care, you’re an activist.”
While Longshot’s last album, Struggle Music, was about adversity, this one is about how to respond to it—namely, without resentment or bitterness. Instead, he encourages listeners to “celebrate yourself by letting poison go,” he says. “I want to spread love. We’re so dark right now. I want to be like a torch. You’re a torch. When you touch mine, you light up and you spread your light to someone. That’s how we light up the world.”
Now 39, Longshot embodies this philosophy. His smile beams, enviable lashes frame his big brown eyes, and he exudes a zealous energy that seems too big for his body. Any lingering trauma from childhood he now processes through music. “This is literally my therapy. This is how I talk to my brothers, how I talk to my mom,” he says. “It’s for them. It’s for us. It’s the most important thing in my life. It’s all aligned. My music fuels my love for life, which is my family and my friends, and that love of life fuels my music. It’s one.”
Describing his dream—to one day buy a home and distribute keys to all his siblings—Longshot gets emotional, and apologizes for it. “I still haven’t gotten that house and our family’s still messed up,” he says. His grandmother recently had a debilitating stroke, and he’s unsure if she even recognizes him anymore. “I’ve never had anybody in my life die. No one,” he says. “I’ve been fortunate in that sense.” His mother, now 16 years clean, is dying of liver cancer; several of his siblings are not on good terms with her.
“She has this ball of fire inside of her. I don’t care how many days you go to church, I don’t care how many times you found God, how much you don’t curse. It’s still inside of her,” Longshot says. And yet, he adds, “I don’t hold nothing against her. My mother made me. Even I have crazy feelings [about her], obviously, but I would never turn on her. I’m the only person she has to dump on.”
Longshot is unmarried and has no children, but the local music scene has become as much of a home as he could ask for. “This scene is so cohesive and so close-knit,” he says. “Chicago is not like that. It’s the complete opposite.” And he feels like he’s a part of creating a sound and an identity for local hip-hop. “I’m so appreciative and so blessed. I feel very lucky to be able to say that I was alive and making music during this time in Minneapolis.”
Longshot and Lazerbeak
With: Holidae, Angel Davanport, Purple Orange Beach
Where: 7th St. Entry
When: 9 p.m. Wed. July 4
Tickets: $10/$12; more info here