Abbas Kubaff
Although he never achieved the commercial success of some of his peers or newer entrants, Abbas is a surgical lyricist idolised for his clever wordplay. He has been in the music industry for well over 20 years. His earlier works Nairobism and Nairoberry alongside Bamboo, showcase his skill in album-making. His 2002-2006 run saw his hard-shell raps hand Hip Hop a space in the mainstream, at least.
Wakadinali
Perhaps the hot take of the list, and even the most controversial, but Soundcity Africa nominees Wakadinali ticks all boxes. From an underground crew that has been in the game for well over a decade now, they have exceeded expectations. No Kenyan acts express inner-city dwellings, youth rumblings and takes on everyday like Wakadinali. To break through the glass ceiling in this fashion, they have established street and mainstream credibility seamlessly.
They have outgrown the underground through numerous outings on features with major acts, as well as cyphers and projects that act as odes to their surroundings and upbringing in Kayole. Maintaining their rugged style and not going "pop" also extends their appeal and emphasises their originality. Additionally, 'Ndani Ya Cockpit 3 is a project across all genres.
E-Sir
Probably the shortest discography among the lists' contingent, it would be blasphemous to omit him from the list. The South-C prodigy single-handedly carried urban Kenyan music with his hit songs Huu Mwaka, Mos Mos and others into the limelight. E-Sir's music was original and packed with substance, hence why it is highly acclaimed monumental decades after his death. From boastful yet feel-good cuts like Saree to introspective tear-jerking numbers like Hamnitishi, the lyrical tongue twister is immortalised in Kenyan books.
Nyashinski
The self-proclaimed G.O.A.T (greatest of all time), Nyashinski is a star act. With melodic yet poetic cadences, when he graces a microphone to rap, he does not disappoint. Coming onto the scene with crew Kleptomaniax, Nyash was a wide-eyed rapper yet to complete high school when the masses heard of him.
Nyashinski lived in Kenya until 2006, when at 21 and a member of a rap trio, Kleptomaniax, his family relocated to Delaware, US where he worked as a truck driver for 10 years until his return to Kenya to continue his music career in 2016. His Lucky You offering was a textbook performance in album curation and will be heralded as one of the best hip hop albums of the last decade.
Khaligraph Jones
The most awarded emcee on the list, Khaligraph Jones has been crowned Africa's Best Rapper even by non-Kenyans.
Scoring records with some of the best emcees in the continent including Sarkodie, who is touted to be the best in Africa, Khaligraph has held his own. His machine-gun-like flow and intensity on the song have been highly adulatory. Khaligraph can make songs and conjure up freestyles in a fashion no one on the list can. His crossover ability is also potent hence why he easily ranks in the Top 5.
Octopizzo
Besides Khaligraph Jones, Octopizzo is one of Kenya's top rap stars. He symbolises the heroism of making it out of adversity through music. Octopizzo's success story cannot be ignored, even if critics vilify his cringe and crass punchlines arguing they can be a barrier for how high he ranks on the list. His expertise in making perpetual music that sticks, marrying artistry and creativity, and his nimble sense of fashion and experimentation set him apart.
Efforts in Noma Ni crystallise his style and paint him a classic example of black excellence. He is a trailblazer and continues to inspire upcoming rappers.
King Kaka
From Kaka Sungura to King Kaka, the evolution of Rabbit has been phenomenal. As an emcee hailing from Buru Buru Estate in Nairobi, Kaka's formative years included hits such as Jam Nakam before he rallied on in the industry with numerous hits such as Ligi Soo.
His business acumen is also impressive, and he has partnerships with high-end brands such as Remy Martin. Kaka, beyond music, is an executive in Kaka Empire that has funnelled careers for artistes such as Femi One. His eye for talent and continuity in music and the arts is undeniable.
Collo
When it comes to flows, not many can beat Collo. He is a gem that can run rings around any emcee given the chance. He boasts numerous classics such as You Guy, Tuendelee and his stand-out verse on anthems such as Party Don't Stop place Collo in the echelons of urban Kenyan music lore.
Relentless and acrobatic with his rhymes, Collo shot Kenyan music up when the international floodgates began to open and Kenyan music was at its arguable heights before the explosion of Afrobeats.
STL
Gracing the list as the only femcee, Stella Mwangi's glaring style and braggadocio has been hard to mimic. Possessing a swagger and relatability yet being inaccessible at the same time, Stella has songs that will stand the test of time.
Hits like Dreamer, Happy, Biacara, and Bad As I Wanna Be are in the billing for the best Kenyan songs ever. Although she relocated to Norway, Stella is a pearl of Kenyan talent and has seen her music synced in shows such as CSI.
TNT
When it comes to English rap, the slogan "It is not about who did it first, it is about who did it right", and Timmy & Twenny are perhaps unknown, but have the quality and catalogue to compete.
Their magnetic yet ostentatious style is the reason mainstream artistes such as Khaligraph keep them close. Individually, Timmy Blanco is light years ahead of even American rappers on a skill level. Meanwhile, Twenny is the evil part of the faction that contains a diabolical rap sense.
T&T have closely collaborated with Wakadinali, and Tellaman (SA) and continue to keep pushing the envelope when it comes to being an anomaly in the Kenyan music industry through English raps, a trait that is not quite well received in Kenya.
