Fans of Winky D say he has already surpassed the late Leonard Dembo, reigniting a long-running debate over Zimbabwe’s greatest musician of all time.
Harare – Zimbabwe’s music scene is once again gripped by a familiar, emotional, and deeply divided conversation: who is the greatest of all time?
By Advent Shoko
This time, the spotlight is firmly on Winky D, with a growing section of fans boldly claiming the dancehall star has already surpassed the late sungura legend Leonard Dembo.
It’s a claim that has stirred strong reactions across social media and music circles, reopening a debate that has long featured giants like Alick Macheso, Oliver Mtukudzi, and Thomas Mapfumo.
For decades, Dembo has held a near-mythical status. Known for his perfectionism, he delivered timeless hits like Chitekete, a song many argue still outclasses modern productions despite being recorded in the analogue era.
But Winky D’s supporters believe the numbers, influence, and longevity tell a different story.
One fan, in a widely shared comment, went as far as saying:
“Chakaitwa naDembo chisati chaitwa naWinky D kufa chete otherwise zve music akadarikwa kudhara, chete in Zim tinosimbisa munhu akafa kudarika muupenyu.”
Roughly translated, the sentiment suggests that the only thing Winky D has not done compared to Dembo is die, otherwise, he has already surpassed him musically.
That bold claim echoes themes from Winky D’s own music, particularly in tracks like Sando Dzangu, where the artist openly demands recognition for his achievements.
Yet, not everyone is convinced.
Critics argue that while Winky D is a dominant modern force, Dembo’s vocal quality, composition, and timeless appeal remain unmatched. Some even insist that Chitekete alone outweighs Winky D’s entire catalogue, an opinion that highlights just how deeply rooted Dembo’s legacy is.
Others broaden the debate, questioning whether the GOAT conversation should even be limited to just two names. Figures like Mtukudzi and Mapfumo continue to loom large, while Macheso’s consistency over decades raises further questions about longevity versus impact.
There’s also the lingering “what if.”
Dembo passed away in his early 30s, leaving behind a catalogue that many believe would have grown even more influential over time. Would he have maintained dominance for decades? Or would newer sounds have reshaped the conversation anyway?
In the end, the debate says as much about Zimbabwean music culture as it does about the artists themselves.
It’s about legacy versus longevity. Influence versus innovation. Emotion versus metrics.
And for now, there is no final answer, only a conversation that refuses to fade.
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