Jack Red Credit: Kyser Photography

For years Jack Red and his distinctive voice have been the secret ingredient in Chicago’s new soul-infused, experimental hip-hop sound. His supporting vocals work their magic on the upbeat “Lovely Day” from Vic Mensa’s 2013 mixtape, Innanetape, and in 2015 he was part of the all-star cast that joined Donnie Trumpet and Chance the Rapper on the masterful album Surf. You can hear Red flex his range on “Wanna Be Cool” and “Sunday Candy,” the latter of which he performed with Chance on Saturday Night Live last year.

Now Red is ready to show the world what he can do on his own. His new single and video, “Sometimes,” is his first release as a solo artist. It will appear on an upcoming concept R&B record addressing subjects near and dear to him—including love and marriage. Red, born in Auburn-Gresham as Jabari Rayford, is 25 and newly wed to his high school sweetheart, Kia. “She’s a beautiful bundle of amazingness,” he says with a big smile. Shot by Visual Season, the video includes footage from their wedding, held in May 2015 in Punta Cana on the eastern shore of the Dominican Republic, and it shows Red contemplating leaving the bachelor life to say “I do.”

“My parents have been married for 30-something years, but now they’re separated,” Red says. He started writing the song before his nuptials, but didn’t finish it until after. The first verse introduces us to a seemingly nervous Red, who sings, “It’s the day before my wedding / But it’s you that’s on my mind / Can’t help how I feel / Who knows if it’s real / Or just a waste of time.”

On the second verse, he talks about his parents and wonders how they made their marriage work for so long. Because they were separated when he first considered getting married, he questioned whether his own marriage would last forever. “That’s where the aspect of choice comes in,” he says. “You have to choose to fight for something. You have to choose to devote yourself to something, commit to something, and hold yourself to that.”

“Sometimes” is just a snippet of what will be a wide-ranging project. Red plans to talk about more than just the hard work of marriage—he also wants to incorporate conversations he has with himself and his friends about romance, commitment, and Chicago’s violence. He hopes his positivity can help undo some of the negative mainstream stereotypes about black men.

“I understand everybody didn’t come from where I came from. Everybody didn’t have what I had,” Red says—that is, he knows he had some advantages because he came from a two-parent home. But he’s no stranger to racial profiling (he says he’s been pulled over for being a black man with dreads), and he saw his first bloody body in his neighborhood at age 12. “I show the fact that I came from the same neighborhood, and I saw these things—and you have too—but I’m choosing to take this [positive] route, and it doesn’t make me any less cool. It doesn’t make me any less of a man.”

Red’s father, Maurice Rayford, is the lead singer of Motown tribute band the Moods. His mother, Diane Love Rayford, also sang a bit in her heyday. “My mom said I came out the womb singing,” Red jokes. As a child, he studied piano, percussion, cello, and trombone—but trombone didn’t stick. Eventually he turned his parents’ basement into a makeshift recording studio with the help of his father’s old Dr. Fong loudspeakers, an old 16-channel mixer, and a TV-dinner tray to hold up his keyboards.

Since 2010, Red has worked as an engineer at Soundscape Studios in Humboldt Park, which is also where he produced and recorded most of “Sometimes.” The song’s string accompaniment, performed by rapping violinist Lil Sharp, was recorded at a hotel in New York.

Through his music, Red wants to confront society’s ideas about marriage. He says he understands why some men find it convenient to be dismissive of women or view them as sex objects, referring to Chris Brown’s “Loyal” (where he declares, “These hoes ain’t loyal”) and to Future’s polygamous lyrics. But while that may be fun, he says, it’s damaging to the success of the black family.

“Are we as men really loyal? Can we be honest and say I’m not married because I don’t know how to be married, or I’m not married because I’m not strong enough to make the commitment necessary?” Red asks.

“I want to be that artist that 10, 15 years from now you look back and say, ‘He helped me get through that.’ Whatever it was,” he says. “I just want to have raw, real, relatable music that can inspire and affect a generation.”

Below you can watch the video for “Sometimes.” Click through for a higher-resolution version.
Correction: This post has been amended to correctly reflect Jack Red’s place of birth.