In the other is the real President of Uganda, Yoweri Museveni, who -- like many of Africa's former revolutionaries -- has clung to power for decades, amid growing calls for him to step down.
Museveni, 73, has ruled the east African nation with an iron fist since he took power in 1986 and is not known to be soft on his opponents; he has seen off many of them in his 32-year rule.
But some commentators are saying that Wine -- with his musical and political clout as well as a solid youth base -- is the real challenger to Museveni's throne.
"Bobi Wine poses a real threat to Museveni, more so in consideration that young Ugandans, many of whom are unemployed, constitute a huge percentage of the active electorate," says Jimmy Spire Ssentongo, an Associate Dean at Uganda Martyrs University.
"Given the widespread public desperation in Uganda, all many people want is a person who shows the potential of removing Museveni. All else is secondary," he said in an interview with The Conversation.
Before he was Bobi Wine, the musician was known as Robert Kyagulanyi. He grew up in the slums of Uganda, raised by a single mother, but turned to music as a way out of grinding poverty.
His upbeat dancehall music style and catchy lyrics dominated airwaves and clubs across East Africa from the early 2000s.
Singing frequently in his native Luganda, the songs contained strong messages, often railing against social injustice in the country.
He called on the citizenry to "rise up and raise their voices" to challenge oppression.
"Don't shy away from working for Uganda, because it is your own country, even if your boss was not your choice. Just play your part, because this is your country," he sang in one of his hits, "Situka."
With such politically conscious lyrics, a career in politics was, perhaps, inevitable.
In 2017, he stood for Parliament as an independent, campaigning on the catchphrase: "Since Parliament has failed to come to the ghetto, then we shall bring the ghetto to Parliament."
He was elected by a landslide and has since proved to be a thorn in Museveni's side, pitching his tent with opposition legislators and continuing to make music, mostly critical of the President's long-term rule.
His popularity has not gone unnoticed by the government.
Some of his songs, including "Freedom," have been banned in the country.
"See our leaders become misleaders," Wine sang. "And see our mentors become tormentors. Freedom fighters become dictators. They look upon the youth and say we're destructors."
Bobi Wine, 36, was a toddler when Museveni came to power.
A former defense minister, Museveni had formed a political party that would go on to overthrow the brutal Idi Amin dictatorship in 1979.
More than 70% of the country's present population was not yet born when he became president.
Uganda has one of the youngest populations in the world; more than three-quarters of the country's 35.6 million people are below the age of 30.
According to the International Labor Organization, young people form 83% of the unemployed in Uganda.
Many are frustrated and long for opportunities that will lift them out of poverty.
President for life?
Once revered for unseating one of Africa's most brutal leaders, Museveni himself now runs the risk of becoming a dictator.
He has changed the constitution twice to extend his stay in office. In 2005, legislators removed presidential term limits to allow him to stand for elections.
A bill was also passed last year eliminating constitutional limits on anyone serving as president past the age of 75, paving the way for Museveni to become president for life.
When it was debated in Parliament, Wine joined opposition MPs to shut down the law.
He said in a Facebook post that it was time for Museveni to release his firm grip over the nation.
"Ugandans made it clear long ago that they are opposed to a life presidency," he wrote. "They don't want the constitution tampered with in any way."
Arguments during the presidential age limit debate descended into chaos as lawmakers exchanged punches and threw chairs at each other in Parliament.
The amendment also sparked protests among students and activists.
#FreeBobiWine
Wine has used his star power and political office to galvanize Uganda's youth to take action against unpopular policies.
When the President introduced a controversial social media tax earlier this year, Wine led a protest march to Uganda's Parliament to demand a review.
However, he is not without controversy. In 2014, the pop star was forced to cancel a UK tour after he was denied entry into Britain following protests from gay activists who accused him of promoting homophobic lyrics, according to the UK Guardian.
He later wrote: "I am personally not out to threaten the life of any individual based on their sexual orientation, I just do not agree with them (homosexuals)," he said. "This is my opinion and happens to be that of 99% of Ugandans," the newspaper reported.
Following his arrest and alleged torture, Wine has gained global prominence and sparked an international protest movement.
The lawmaker was arrested on August 15 alongside opposition MPs after rioting broke out between rival parties ahead of a local parliamentary election.
Wine said on Twitter that his driver was shot dead. Police said Museveni's car was attacked in the aftermath of the violence.
The public has reacted to the recent events with outrage and anger, most of it channeled through social media.
From Tokyo to Washington, activists and fans joined the #FreeBobiWine hashtag online and took to the streets to demand the singer's release.
Influential figures in the music industry, including Chris Martin, Angelique Kidjo, Damon Albarn and others, also joined the campaign.
Thousands of Kenyans marched to the country's Parliament and the Ugandan embassy in Nairobi to hand over a petition for the singer's release.
'A brutal regime'
Kampala's Mayor, Erias Lukwago, told CNN Wine's arrest has exposed Museveni's "brutal regime."
"The level of injustice in Uganda is too much; this brutal regime wants to suppress opposing voices. But they must know that Ugandans are angry, and they will no longer tolerate any form of oppression," Lukwago, who is also on Wine's legal team, said.
The singer, now facing treason charges, was taken into military detention following his arrest. He posted a lengthy statement Monday detailing the physical abuse he says he suffered at the hands of the military during and after his arrest last month.
Wine, who is seeking treatment in the United States, claims to have been beaten with an iron bar, punched, kicked, hit with pistol butts and had his ears pulled with "something like pliers."
"After some time, I could almost no longer feel the pain. I could only hear what they were doing from afar. My cries and pleas went unheeded. The things they were speaking to me all this while, I cannot reproduce here. Up to now, I cannot understand how these soldiers who I probably had never met before in person could hate me so much," Wine says in the statement.
Police spokesman Patrick Onyango told CNN the allegations are being investigated.
"There are allegations -- they are alleging that they were tortured by security forces. There is already a case file open to investigating their allegations of torture, so the allegations of torture has also to be proven by medical examinations. I cannot believe what they're saying unless the medical personnel confirm to us that they were indeed tortured. Until the medical team from the government ascertain or confirms to us that they were tortured that's when I can say they were," he said.
Museveni also took to his blog and social media to dismiss the torture allegations as "fake news."
He accused Wine and the arrested MPs of intimidating voters.
"Anybody who is a friend of the young politicians like Bobi Wine should advise them that shortcuts like cheating, importing voters, intimidating the voters of the other side, ballot stuffing... will lead them and Uganda to doom," Museveni said.
Clinging to power
While much of the developed world embraces the energy of youth in leadership positions, it is not often the case in Africa.
From Uganda to Cameroon, many of the continent's leaders are aging and clinging to power while their countries struggle to keep pace with global developments.
Zimbabwe's Robert Mugabe was forced to relinquish power in 2017 after 37 years of autocratic rule. The 94-year-old had ruled the country since its independence in 1980.
Cameroon's Paul Biya, 85, has been President since 1982 and plans to stand again for election in October, amid spiraling violence and alleged human rights abuses in the country.
It is no wonder young politicians like Wine attract a strong and loyal following when they go up against these regimes.
But Wine is quick to reject notions that he is a messianic figure who will topple Museveni's long-standing regime.
As he puts it in a recent tweet: "I have said it before that any party that tells you that it can single handedly liberate Uganda is a jocker (sic). For us to defeat President Museveni, it will take more than one political party, more than one tribe, more than one religion and yes, more than one generation."
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