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Before the dazzling lights and the roaring crowds, musician Diamond Oscar, real name Oscar Mbabali, navigated the gritty streets of Kampala, honing skills that would later define his path to stardom.
Famous for his mid-2000s hit "Awawa," Oscar recently peeled back the layers of his past, revealing a compelling narrative of teenage grit and ambition that propelled him from a shoeshine boy to a celebrated artist.
His journey began at a tender age, setting the stage for a series of entrepreneurial ventures that, though challenging, ultimately laid the groundwork for his musical aspirations.
The Early Scramble: A Taste of Kampala's Hustle
Oscar’s initiation into Kampala's demanding economy began at just 16 when he joined his uncle's shoeshining business.
This early exposure to urban commerce soon led to an even more arduous undertaking.
A customer, a seller of herbal medicine, once approached him with an offer to hawk his wares.
This, Oscar recalls, was "the toughest job I ever did."
The sheer physical exertion of carrying the medicine, coupled with endless hours of walking through Lukaya Town and surrounding villages, was exhausting. For his efforts, he would receive a meagre Shs 2,000 at the end of each day.
Driven by an entrepreneurial spirit, Oscar soon decided to venture out on his own.
With a modest capital of approximately Shs 25,000, he headed to Owino market.
His first independent venture was selling roasted groundnuts. He purchased a basket and three kilograms of groundnuts, eager to start his new hustle.
However, a crucial detail escaped him: the art of preparing them. The entire batch was burnt, a disheartening setback that saw him generously donate his burnt produce to the street children.
Undeterred, he moved on to hawking polythene bags to shoppers downtown, a venture that proved equally unprofitable, yielding only about Shs 3,000 daily.
Diamond Oscar
The Second-Hand Market and a Brush with the Law
Oscar's fortunes began to shift when he transitioned into the second-hand clothes market in Owino.
Here, he encountered a man named Lindo, who was in the business of cutting bales of jackets.
Inspired by the potential, Oscar made his first investment, purchasing two jackets for Shs 1,500 each.
He meticulously ironed them and set out to hawk them. The immediate return was astonishing: both jackets sold for a combined Shs 30,000.
This instant success validated his instincts, and he dedicated the next year and a half to selling shirts and jackets, even employing other youngsters to hawk for him across the city.
His entrepreneurial scope expanded to include mosquito nets and curtains, diversifying his income streams.
However, the informal nature of his business brought him into direct conflict with the Kampala Capital City Authority (KCCA).
Constant arrests became a recurring challenge, and Oscar himself was eventually apprehended and taken to City Hall Court.
Many of his fellow hawkers were remanded to Luzira Prison.
Yet, Oscar's quick thinking saved him. When he stood before the magistrate, he fabricated a story, claiming to be an orphaned student who had come to the city to collect school fees from his vendor uncle.
He explained that his uncle had fled during the KCCA raid, leaving him to be arrested. Sympathetic to his plight, the magistrate immediately ordered his release.
It was during these formative years of relentless hustling that Oscar’s aspirations began to pivot towards music.
He found inspiration in the established artists of the time, many of whom he encountered through his various street ventures.
Jose Chameleone was a frequent customer, often buying sunglasses from Oscar at DV8 Bar.
Other influential artists like Steve Jean, Michael Ross, Vamposs, and Red Banton were also part of his orbit.
He spent considerable time observing and interacting with them, absorbing the nuances of the music industry.
These informal apprenticeships and close proximity to his idols eventually provided the impetus for him to embark on his own singing career, transforming the street hustler into the celebrated musician known as Diamond Oscar.