Masego is a saxophone player, a singer, a rapper, a comedian, a DJ – a singular talent and
surprising presence in the musical fabric right now. He cites the 1930s Harlem big band leader and singer Cab Calloway as a guiding spirit, was mentored by DJ Jazzy Jeff, and puts an unabashedly sultry-smooth spin on the R&B, hip hop and dance music that he and his contemporaries like Chance The Rapper, SZA, Goldlink and Smino are making. 2018 is proving to be Masego’s breakout year as he makes his official full-length album debut Lady Lady, the culmination of years of hard work, crossing the globe multiple times, and refining his distinctive craft.
He towers over 6ft tall with a gold saxophone pendant around his neck, robed in impeccable threads and with tattoos that spell J-A-Z-Z across his knuckles. And Lady Lady is a showcase of his many sides: funny and flirty, wide-eyed and coming-of-age, mysterious and moody. The title track paints him as a jazzy heartthrob, a young sax-playing D’Angelo. Elsewhere he’s influenced by trap,Caribbean styles, electric piano funk, and more somber textures. “It’s the many emotions of Masego,” he smiles. One of his main collaborators is producer Sounwave of the TDE family. Sounwave has put a pep in his step. “He’s allowed me to write in a legendary way: like Michael Jackson or old school Stevie [Wonder].”
Masego lived a nomadic youth, moving around with his Jamaican-American father who was in the air force, and his Georgia-born mother. Both are pastors and he lived what he calls a sheltered life, eventually settling in Virginia for Middle School. He first encountered music in church and his upbringing was strict. “We weren’t allowed to listen to hip-hop at all.” When he was eight, he was blown away by a church drummer and taught himself. “YouTube taught me everything I know,” he says. He picked up piano and saxophone too.
College was where Masego blossomed. He did a decade’s worth of growing up in a matter of months. He built up a reputation at open mic nights. Then discovered the looper pedal on YouTube,bought one and started writing his own stuff while freestyling in his dorm. “I’d make up songs about nothing,” he says. “Try them out at talent shows and lose badly.” Masego felt most comfortable hiding behind his instruments. Until he noticed one of his peers singing original music at an open mic, garnering attention from the ladies. “I knew I was missing something, so the voice was the next journey,” he says. Getting back to work on making a beat from scratch, Masego played his saxophone and began rapping and scatting over it.
In college, all this music Masego missed out on fell into his lap: Outkast, Kanye, Lupe Fiasco. And life started to happen. Masego unearthed his appreciation for women. He fell in love – and lust. He got hurt. “I’m still going through that process,” he admits. “When I wrote my best songs in college it’s because I was dealing with my version of heartbreak.” He had a band and invented a genre: 'Trap House Jazz’. A Soundcloud freestyle called 'Girls That Dance’ went viral and caught the attention of DJ Jazzy Jeff. “I got some tweets that Jazzy Jeff was playing my song in Amsterdam. I tweeted him back He DM’d me to come to his house. It was actually his house,” he says. “He’s been my uncle
It was in Jeff’s company that Masego began to rub shoulders with the likes of producer Young Guru, Jill Scott, Will Smith. “Half of me was starstruck,” he says. “I’m a music nerd. I appreciated them talking about what went into making their records. I was trying to get educated.” In that time, he was looking to the likes of Pharrell Williams, Frank Ocean, Childish Gambino and Tyler, The Creator as the types of creatives who are truly forging their own paths; an intention Masego shares.
In Los Angeles, Masego has continued to keep good company. Having been in rooms with Kendrick Lamar, Flying Lotus, Thundercat, J Cole, Rapsody, etc, he’s come face-to-face with a reality that’s not beyond his own grasp. “I’ve interacted with all my heroes,” he says. Back in Virginia, he’d visit DC as rapper GoldLink was coming up. They became friends, and Masego credits him with keeping him down to earth. “I’ve seen his local shows, seen someone go from locally known to having a Number 1 hit single. That’s my best shot at not making mistakes,” he says.
At its core, Lady Lady is all about his experiences with women and how women made him see more of himself. “Whether that’s a conversation, a relationship, a one night stand… Was it inspirational? Did it hurt me? Did I learn something? Did I feel confused afterwards?” Aside from women, Masego’s life is all music at the moment. His favorite thing to be is bored. “That’s when I get creative,” he says.Cultivating a strong family around him is of prime importance, too. “I want people to win with me,” he says. “Because winning’s inevitable.”