PICTURES: The Changing Faces of Bobi Wine

Singer turned politician Bobi Wine real name Robert Ssentamu Kyagulanyi is the most trending person in the country after his controversial arrest in Arua district as a result of the chaos leading to the Arua Municipality by-elections last month.

He returned home yesterday, Thursday 20th September 2018 after two weeks in USA where he was receiving treatment.

Bobi Wine a few days back. He has come a long way to become the man he is today

Besides being a musician and politician, Bobi Wine is also a businessman and entrepreneur.

He is currently serving as a member of parliament for Kyadondo East Constituency, Wakiso district.

Bobi Wine was born on 12th February 1982 in Kanoni, Gomba, and former Mpigi district. His father Jackson Sentamu passed away.

Bobi Wine (L) when he was just starting out his singing career

He is married to Itungo Barbra Kyagulanyi whom he met during her senior six vacation and they have four children together; Solomon Kampala as the first child, Shadrack the second, Namagembe Shalom the third and Suubi Shine Nakaayi the last born.

He emerged on the scene in the early 2000s with his captivating lyrics and soon became a household name especially in ghettos where he is a self-styled president.

Bobi Wine with Barbie on his graduation day

Back then he was the poster boy for Marijuna consumers. With dread locks, Bobi Wine was considered by many a riff-raff.


Over the years, the ‘Kyarenga’ singer has had a major transformation regarding his looks. From the days of not-so-good looking dreads, to cornrows and a clean shaven head he wears today.

Bobi Wine and Juliana Kanyomozi at corporate dinner, Hotel Africana over twenty years back

Being a politician, Bobi Wine looks nothing like his former self and more polished.

ChimpLyf takes you through how the appearances of Bobi Wine have changed over the years through pictures.

Bobi Wine with former manager Lawrence Labejja
Bobi Wine with Chameleone and Bebe Cool in the early 2000s
Bobi Wine was a known weed smoker
Bobi Wine lights a joint
Bobi Wine before he cut off the long dreads
Bobi Wine with Buchaman
Bobi Wine on his 33rd birthday, with Nubian Li and Coco Finger
Bobi Wine founded Fire Base
Bobi Wine with wife Barbie on their wedding day in 2011
Bobi Wine with family
Bobi Wine with his family after joining politics
Bobi Wine greeting President Museveni
Bobi Wine with wife Barbie on one of his boats
Bobi Wine during one of the protests
A mean looking Bobi Wine
Bobi Wine after his arrest
A sad looking Bobi Wine in court
Beauty and the beast!
Bobi Wine with fans at Busabala beach
Bobi Wine with Barbie
Bad man from Dangala Kamwokya
Member of Parliament. Bobi Wine is today polished
Bobi Wine in hospital
Bobi Wine on clutches
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