For over two decades, the Ugandan music industry has been under the influence of three key figures, popularly referred to as the ‘Big 3’: Bebe Cool, Bobi Wine, and Jose Chameleone. Their journeys, filled with rivalry, collaboration, and personal changes, have shaped the Ugandan music. Let’s take a look at their story.
The early beginnings
The story begins in the early 2000s when Bebe Cool and Jose Chameleone found themselves in Nairobi, Kenya. Bebe Cool, having dropped out after his senior six at Kololo Secondary School, decided to pursue a career in music. Despite his efforts, the Ugandan music scene, dominated by Lingala and Kadongo Kamu, proved challenging for him. Seeking better opportunities, he moved to Nairobi.

Reflecting on his decision, Bebe Cool said, “At 18 years, I left Uganda for Nairobi, Kenya for the real struggle that I would be the solution to my mother’s hustle.” Before this move, both Bebe Cool and Chameleone were regular performers at Sabrina’s Pub in Kampala.
Dissatisfied with the limited studio options in Uganda, Bebe Cool’s moved to Nairobi to kickstart his music career. Chameleone joined him a few years later, in the early 2000s.
In Nairobi, Chameleone initially worked as an MC and karaoke performer under the name “Raggaman Jose” at Misawuli Bar. He sought guidance from Bebe Cool, then known as “Bebe Bunton.”
Introduced to the Ogopa Deejays by Bebe Cool, Chameleone collaborated with them resulting in his debut song “Bageya” featuring Kenyan artist Redsan.
This collaboration set the stage for his hits ‘Mama Mia’ and ‘Dorotia,’ which garnered massive airplay in Uganda.
On the other side, Bebe Cool’s breakthrough came with his hit ‘Mambo Mingi’ in the early 1990s. After making a name for himself, he founded the East Africa Bashment Crew in 2005. This group, consisting of Bebe Cool and the Kenyan duo Necessary Noize (Kevin Wyre and Nazizi), produced popular tracks like “Fire Anthem,” “This Tune,” and “Gimme More.”
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The rise of Bobi Wine
As Bebe Cool and Chameleone were establishing themselves, Bobi Wine entered the scene and made a collaboration with Bebe Cool on the track ‘Funtula.’ Prior to this, Bobi Wine had released hits like ‘Akagoma’ and ‘Sunda’ with Ziggy Dee. However, a longstanding beef between Bobi Wine and Bebe Cool soon emerged, a rivalry that has persisted for over two decades.
The root of this feud is often attributed to their differing backgrounds. Bobi Wine, who grew up in the ghetto, differed with Bebe Cool, whose father, Bidandi Ssali, was a Minister in President Museveni’s government. Bobi Wine once remarked that their different upbringings naturally created friction between their respective camps.
The tension escalated when Bebe Cool left the East African Bashment Crew and briefly joined Bobi Wine’s Fire Base Crew. However, due to differences, Bebe Cool soon departed to form his own group, the Gagamel Crew.

This division fueled a competitive atmosphere, with both artists taking public jabs at each other through their music and occasional physical confrontations.
The Battle of the Champions
In 2012, the two artists staged a music battle titled “Battle of the Champions” to determine who was superior musically. Although no winner was officially declared, the event is still talked about to date.
Meanwhile, Chameleone maintained a more neutral stance, continuing to produce music while observing the feud from a distance.
Evolution and current status
Despite the long-standing beef, the ‘Big 3’ have evolved. Bobi Wine transitioned from music to politics, becoming a prominent opposition figure against the ruling government, which Bebe Cool supports.

Interestingly, Bebe Cool and Chameleone have forged a solid friendship over the years. Their bond is often publicly celebrated, especially birthdays.