Saafir, Inventive and Dextrous Oakland Rapper, Dies at 54

Saafir, the raspy-voiced Oakland rapper who infused the rhythms of avant-garde jazz into his rhymes, died on Tuesday morning, according to family. He was 54.

A joint Instagram post by the rapper Xzibit and Saafir’s son explained that the rapper born Reggie Gibson died at 8:45 a.m., surrounded by friends and family.

“We surrounded him and let him know how much we loved him,” the post read. “He can rest now.”

No cause of death was announced. Saafir had long struggled with complications from a spinal surgery and other health problems.

With his early 1990s hip-hop group Hobo Junction, Saafir made a name for himself as a lyrically dextrous and inventive rapper with a distinct, guttural style. He is remembered by hip-hop fans nationwide, and especially in the Bay Area, for incandescently propelling a legendary 1994 on-air freestyle battle between his Hobo Junction crew and fellow East Bay collective Hieroglyphics that lasted more than 40 minutes.

Saafir spent his early teenage years in and out of group homes in Oakland, with at least one stint in jail. Inspired by early rappers like Too Short and LL Cool J, he began writing raps and developing a cadence that frequently avoided the downbeat.

While working with Digital Underground, Saafir was onetime roommates with Tupac Shakur, who introduced the West Oakland-bred young talent to Hollywood movie directors Albert and Allen Hughes. Saafir appeared in their 1993 film Menace II Society as the character cousin Harold.

Before long, Saafir was offered a major record deal from music industry titan Quincy Jones. The resulting album, Boxcar Sessions, bridged the dynamism of jazz innovators like Eric Dolphy and Andrew Hill with the streetwise sounds and themes of crack-era Oakland. To celebrate its release, Saafir performed a free show in front of Leopold’s Records, just off Telegraph Avenue in Berkeley, where Hobo Junction first began selling underground tapes.

Only a handful of albums followed. In 2013, on the blog of hip-hop historian Davey D, Shock G from Digital Underground explained Saafir’s absence from the scene in a sprawling list of accidents, afflictions and obstacles that went viral among diehard fans. Saafir later clarified parts of Shock G’s recollection in an interview with the San Francisco Bay Guardian, where he detailed the challenges of navigating the healthcare system.

Saafir, who used a wheelchair after his spinal surgery, made very few public appearances over the past 15 years. He often made an exception, however, for Dream Day — an annual tribute to his late friend and graffiti artist Mike “Dream” Francisco. In 2014, he appeared onstage in San Francisco to perform his hit “Light Sleeper,” supported by the show’s headliner and his former battle nemesis from Hieroglyphics, Casual.

Though their famous freestyle battle hosted by Sway on KMEL’s The Wake Up Show painted Saafir and Casual as enemies in the public imagination, the two retained their respect for each other.

In a short documentary, The Battle, Saafir commended Casual: “You really brought out the best. You made me wanna be a monster, and I respect it.”

Saafir is survived by a son — the rapper known as Lil Saafir — and a brother. No services have yet been announced.