Listen: Brownstone, “If You Love Me”
D’Angelo: “Brown Sugar” (1995)
“Brown Sugar” is effortlessly cool: In the music video, D’Angelo struts into a dimly lit lounge, sits at the piano, and instantly busts out the sweetest serenade, with smoke from a joint still coming out of his mouth. If you told me that’s how he actually recorded the song, I would absolutely believe it.
In an era when much of the popular R&B singles had been inspired by Teddy Riley’s new jack swing slickness, D’Angelo’s debut hit was a slow-burner that felt beamed in from another universe. Inspired by icons like Marvin Gaye, Al Green, and Stevie Wonder, the Virginia-raised singer pulled from those retro roots while addings elements of hip-hop, helping to lay the foundation for neo-soul. The rap influence is in D’Angelo’s look—cornrows and baggy clothes—but also in the tinny drums programmed by A Tribe Called Quest’s Ali Shaheed Muhammad, which give the song an almost slow-mo bounce. Filtered through the singer’s honey-smooth falsetto and mystic allure, the past and present become seamlessly intertwined. –Alphonse Pierre
Listen: D’Angelo, “Brown Sugar”
Deborah Cox: “Nobody’s Supposed to Be Here” (1998)
Deborah Cox spent the first six months of her music career touring as a backup singer for Celine Dion, a crash course in how to make every note a spectacle. On her breakout hit, “Nobody’s Supposed to be Here,” the smallest shifts are mesmerizing—the jagged edge in her throat when she admits love has knocked her down, the way the vowel caves in when she sings the word “sad,” the shock of shriek that builds up as she belts the chorus. Gentle percussion and chimes swirl in the background, and the song winds around and around Cox’s circular thinking, as she spirals through dejection, hope, and refusal, all leading up to a cathartic key change. “I’m not supposed to care anymore,” she moans as the track trickles out, a final sigh before she gives in. –Dani Blum
Listen: Deborah Cox, “Nobody’s Supposed to Be Here”
Destiny’s Child: “Say My Name” (1999)
Nearly two decades before Beyoncé delivered Lemonade, her heart-wrenching opus on self-transformation and forgiveness in the wake of a partner’s infidelity, she led Destiny’s Child’s glossy, unflinching interrogation of an untrustworthy lover with “Say My Name.” Beyoncé’s staccato, kinetic delivery—which influenced R&B vocal cadences for years to come—is effortless and unrelenting, underscoring her assertion that she is not one to be played. The song is all bravado, and circles a request so elemental that it shouldn’t even have to be asked: to be remembered, and treated with care and respect by someone who loves you. That tension between the audacity of Destiny Child’s performance and the vulnerability of their titular ask imbues the song with an incomparable poignancy. –Vrinda Jagota
Listen: Destiny’s Child, “Say My Name”
En Vogue: “Free Your Mind” (1992)
Appearing on a genre-fluid album laced with doo-wop-like jams like “My Lovin’ (You’re Never Gonna Get It)” and sensual classics like “Giving Him Something He Can Feel,” En Vogue’s “Free Your Mind” took us to rock as thrashing metal guitar riffs layered with keyboards, the group’s signature harmony, and a message of gender and racial unity. “It doesn’t mean that I’m a prostitute, no, no,” these curvaceous Black femmes in thigh-high boots wanted us to know—a radical message at a time when feminism was all but declared dead and a war on women was underway. Slut-shaming and moral judgment were the norm, not the exception, and “Free Your Mind” was an anthem to STFU and leave people be. –Samhita Mukhopadhyay