Cool, who was recently hosted on Urban T.V., claimed that by Wine pursuing a diploma in music, dance and drama at Makerere University, it's an indicator that he was an academic failure.
Bebe Cool wants Bobi Wine to know that there is a huge difference between opposing President Yoweri Museveni and leading Uganda.
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He also appeared to imply that Wine didn't join A-Level though his Wikipedia entry shows that the latter joined Kololo Senior Secondary School, where he attained his Uganda Advanced Certificate of Education in 1998.
Cool studied at the same school after he was denied entry into Senior Six at Makerere College School where he had been from Senior One to Senior Five.
Bebe Cool recently revealed that he scored nine aggregate in Uganda Certificate of Education exams and took a subject combination of Physics, Chemistry and Mathematics in A-Level. He scored five points out of 25.
He didn't proceed to university.
Bobi Wine is currently pursuing a Bachelor of Law at the International University of East Africa.
However, Cool won't stop taunting him about the diploma achievement.
"It means you weren't smart enough to study other courses," said Cool.
"I wouldn't have attacked him if he hadn't run for a position that requires a very smart person," added Cool.
"To be a president, you've to be really smart; exceptionally intelligent," he continued.
"If you use a Senior Four certificate to get a diploma in Music, Dance and Drama, which means you weren't able to proceed to A-Level, an indication that you failed exams. Because school fees were there…”
Cool said: "If you fail to join A-Level, it means you are either mad or you didn't see value in education or you are not clever enough."
He went on: "Opposing Museveni is different from leading a country... a country that's developing doesn't need trials."
Bobi Wine run for presidency in the 2021 elections.