42 Dugg is coming. Much like The Wire’s larger-than-life stick-up character, Omar, the Detroit rapper announces his presence on a track with a simple signature whistle that can sound either welcoming and familiar, or menacing. On a recent afternoon in midtown New York, his mood leaned decidedly toward the former. His new album, Free Dem Boyz, was coming out at midnight, and there was a genuine, palpable buzz for it. (Mere hours after the release, Future, who is featured on the album standout “Maybach,” went viral for lyrics alluding to his past relationship with model Lori Harvey. “That’s my guy Hendrix—he has, like, six nicknames,” Dugg says, laughing.) There’s a lot to celebrate—Dugg has been waiting for this moment. On top of that, he is a naturally excited person. Free Dem Boyz has a theme, and it is meticulously executed. His popular mixtape Young and Turnt 2 struck a nerve in his hometown in 2020, but he’s going for something bigger now. Something that rappers in his position often strive for but don’t always achieve: getting out from under police scrutiny and injustice.
42 Dugg was born Dion Hayes in the notoriously tough east side of Detroit, but ghetto clichés didn’t dominate his life. (“It was cool, man, really. We were having fun, bro. A lot of skating, going to parties.”) Still, in a city that infamously went without a mayor in 2013, after declaring bankruptcy, and a state in which a predominantly Black community still doesn’t have clean water, Dugg found himself getting involved in the street life. At 15, he was sentenced to four years in prison for carjacking and gun possession. The kid who liked to skate and party was sent to jail to rot. A fight with an inmate extended his sentence to six years. He was sent to the hole two times. The first time in solitary was torturous. For 23 hours a day, Dugg had no freedom. The isolation ate at him physically and mentally; he rarely ate. “I would be there for 30 days at a time, and only eating breakfast. I used to get out of that bitch being 110 pounds. I didn’t like any of the food. I would have days where I only ate a cookie a day,” he says. He remembers a sadistic CO who kept taking pants that he had stored away.
At least Dugg had friends—“my homeboy Lou, he made it easier for me”—and his brother, who was placed in solitary with him. The only two things that kept his mind right were learning how to rap and watching basketball; Kentucky became his favorite team. As a youngster he was into Jeezy and Boosie, but didn’t start rapping seriously until his brother encouraged him while they were in solitary. At that point, he didn’t think he was good, but his second time in the hole gave him more time to hone his skills. At 22, he was finally released, and soon after he dropped “The Streets,” featuring fellow Detroit rapper Babyface Ray, on his 2019 debut mixtape, Young and Turnt. The song features a tribute to Dugg’s friend, Eastside Snoop, who was shot to death while sitting in his car on Flanders Street. The chorus is effective: “I done lost my dawg to the streets/He in Heaven ballin’ for me.” Then came a chance meetup shooting craps with Lil Baby in Atlanta. They were competing and didn’t say much at first—“we ain’t talk, we just gambled,” Dugg remembers. Memphis rapper Yo Gotti also got involved after seeing Baby perform at a club in Detroit, and Dugg went from the hole to signing with Lil Baby’s 4PF and Yo Gotti’s CMG labels.
The pandemic was a tough time for emerging artists. Songs that would have usually jumped off in clubs didn’t blast like they should have. Baby, of course, was an exception: His My Turn album topped the charts for five weeks (it is now triple platinum). He brought Dugg along with him for two standout songs. “Grace”’ is decidedly dark, a track dedicated to their old street life in and out of jail. The mood is biting; Dugg is the rapper who stalks his prey. He doesn’t let us forget where he came from, so he can tell us how much he is flexing now: “Three months, dropped near half a million/Fuck a house, I damn near lost a building.” But their second collaboration, released in May 2020, really had hip-hop buzzing. “We Paid” is a bracing celebration of upward mobility, with an earworm of a hook and show stopping lyrics. It starts with Dugg’s whistle, then the snare of some particularly sinister drums lets you know an earthquake is coming. The song’s concept is simple: Baby and Dugg were once on the streets and now they’re rich. Dugg rages, while Baby flows like he is walking a tightrope. It’s an act of rebellion from two men not expected to make it out of their environment. Soon after, Dugg was a star. He credits Baby and Yo Gotti for changing his life: “They make sure I am focused. They make sure I’m on my grind.”
Dugg hasn’t shown any sign of slowing down since then. Free Dem Boyz, which debuted at eight on the Billboard Top 100 after its May 21st release, lives up to the expectations set by “We Paid.” Dugg goes from earnest to braggadocious with ease. “Alone” features him longing for friends that he misses; “Judge Please” is a plea for freedom, made for the homies that are still inside. He got out but they’re still stuck in a vicious cycle of racism and imprisonment. “I for sure owe it to them: They taught me the majority of the things I know. They step the way I step,” he said.
Whatever happens next, Dugg is poised to remain a force in hip-hop. Finally, as we land at Flight Club downtown and he walks around like a rap superstar should—dropping a G on sneakers like Jimmy Conway putting money in a dealer’s pocket—the picture of who 42 Dugg is and what he’s about starts to take shape. He might be small in height, but he carries himself like a giant. The penitentiary CO’s are probably upset.