Of all the musical cultures that have emerged in the past half a century, hip-hop and, in turn, rap have become arguably the most influential of them. The charts say it all: The genre gave us six of the top 10 albums of 2019, according to Billboard (among them: Post Malone’s Beerbongs & Bentleys at #5; Drake’s Scorpion at #6 and Travis Scott’s Astroworld at #8). It’s helped turn streetwear into a phenomenon and rappers, fashion royalty (cue Cardi B on last month’s cover of Vogue US, and all hail A$AP Rocky). And let’s not get started on the Higher Brothers and the late 2010’s explosion of Chinese rap.

Since its inception in the ’70s, the movement’s spread across continents and generations to become a universally recognised sound. It’s even taken root in our very own island metropolis – and far earlier than some might think.

The first ripples of hip-hop appeared in the home-grown music scene in the ’90s, when airwaves were more favourable towards alt-rock outfits like Concave Scream and Humpback Oak. While hip-hop in the US was having its now-revered Golden Age, Singaporeans were getting acquainted with an unprecedented duo known as Construction Sight, comprising Sheikh Haikel and Ashidiq Ghazali. Cheeky and rambunctious, they would go on to clinch the Grand Championship of the then-renowned talent show Asia Bagus!, thrusting them and Singapore rap into the national spotlight.

Thus sowed the seed that would grow into a tree of influence. The noughties saw the birth of other remarkable local hip-hop groups such as Triple Noize and Urban Xchange; the latter even scoring a Coca-Cola campaign. There were also solo wordsmiths like the pop-inflected Mark Bonafide and underground-influenced Akeem Jahat, both regarded as pioneers who helped take rap here beyond the old school. It was official: Singapore rap was no longer an abstruse notion or something blatantly borrowed. People were sitting up, taking notice and making it our own.

Rap’s always been the vernacular of the streets with raw lyricism touching on topics close to home. To give their brand of rap a distinctly +65 flavour, performers here have often incorporated references to our multiracial culture and the use of colloquial slang into their tunes. “There’s no music genre here that represents Singapore as much as hip-hop,” says one of the scene’s most popular millennial stars, Kevin Lester.

Better known as THELIONCITYBOY, or TLCB, the 35-year-old’s become an ambassador of the genre with his clever, edgy tunes that include most recently a playful ode to our first female president. Meanwhile fellow household name ShiGGA Shay’s earned a reputation for infectious anthems like Lion City Kia that fuse English with Hokkien lyrics that only a full-blooded Singaporean would understand. (FYI: Both have gone on to perform at the National Day Parade.)

Now, a whole new generation of talents is adding diversity, richness and plenty of swagger to the scene. For a while, the feisty Masia One, or MAS1A – who’s collaborated with Wu Tang Clan’s RZA and blends her Asian roots with Jamaican influences – was the only prominent name carrying the torch for female emcees. Joining her today: the likes of the soulful, modern songbird/rapper Akasha and the no-holds-barred Sheeq Luna who delivers messages about self-empowerment over heart-thumping beats.

And with their penchant for highlighter-hued hair and tracksuits and the charisma to match, the multilingual Fariz Jabba and Yung Raja have become our Gen Z answer to Slick Rick: as loved for their stylistic choices as they are for their witty, catchy chants loaded with mentions of our local way of life. Both were headliners at the Marina Bay Singapore Countdown, which – like it or not – is often considered a big deal. (Remember the year when K-pop superstars Big Bang performed?) Now, who has doubts that Singapore is truly a rap nation?

The Fresh Prince: Fariz Jabba   

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Just like many of the scene’s most prominent male artistes, Fariz infuses local slang into his rhymes, busting out panache and punchlines in English and Malay. A silver-tongued freestyler, the young gun wants his listeners to enjoy his art as a platter – “pick what you like, put aside what you don’t”. But with his streetwise swagger, intrepid originality and down-to-earth charm, there’s plenty to love. His 2019 Malay ballad Masa not only showcased his R&B crooning capabilities, but also his fancy footwork in its choreography-rich music video. Getting signed to Def Jam’s recently launched South-east Asian label only means an even more exhilarating year ahead. (This page and opposite) 

The King of the Jungle: THELIONCITYBOY

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His real name: Kevin Lester. Before putting his proverbial mane on though, this 35-year-old was already changing the game with memorable stints in bands including Bonafide Vintage Flav’r and SIXX. Overflowing with charisma and unbridled talent, the “veteran” is now widely respected as one of the island’s proudest exports, with compositions that straddle the line between heart-on-sleeve patriotism and rebellious bravado. Little wonder that he’s now signed to Sony Music Singapore – his first label deal. 

The Rap Vixen Reinvented: Sheeq Luna 

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For years, this R&B chanteuse has been building a name in the underground scene for her collaborations with the likes of ShiGGa Shay and OG Sheikh Haikel. Boasting versatility in spades as both an eloquent emcee and soulful vocalist, she released the smoky single Mama last year only to kick off Sheeq Luna 2.0. “It’s time for people to start knowing me for my actual self, through what I genuinely want to put out and not with the input of 50 other people,” she says. “As a writer, I believe in making the few minutes that we have in a song worthwhile. The style’s got to be fresh; the content easy listening yet impactful and timelessness is key.”

The Aspiring Newcomer: Akasha

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Simmering and glimmering, the modelesque Akasha is bringing her A-game to the hip-hop scene here. Shutting down naysayers, the aspiring emcee approaches music with positive vibes and lyricism pertaining to love to be “an inspiration for the youth of today”. Her debut single bad luv rolled out last month and she promises more fired-up collaborations with her pals from the local music scene. To quote that all-time favourite Ciara goodie: “The princess is here.”

Our Answer to A$AP Rocky: Yung Raja

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Proudly brandishing his ethnicity within his music, Yung Raja criss-crosses his lyrical flow with both English and Tamil verses. His breakthrough came with the 2018 anthem Mustafa, which gave nods to the renowned 24-hour shopping centre. Fervently captivating onstage, he’s also become regarded as a style star with his idiosyncratic take on sportswear and accessorising. Just watch the hyperstylish music video for his infectious single Mad Blessings, his first release after signing with Def Jam South East Asia last year.

Photography Stefan Khoo, assisted by Yann Cloitre Styling Imran Jalal, assisted by Jamie Lee Hair Sean Ang Makeup Melissa Yeo, using Gucci Beauty Text Kevin Ho