Sceptics feared Zelensky would turn out to be a puppet leader, controlled by oligarch Ihor Kolomoisky who backed his campaign and had been under investigation for fraud and money laundering.
But Zelensky proved to be more independent than his doubters thought, and the anti-corruption drive by his administration has had some success.
Many Ukrainians also viewed Zelensky’s rhetoric on the conflict in the eastern Donbas region and relations with Russia as too timid, says communications consultant Yaryna Klyuchkovska.
As the drumbeat of war grew louder, Zelensky continued to emphasise his hopes for a diplomatic solution, even while Ukraine was reporting a rapid increase in ceasefire violations along the front line.
His attempts to negotiate with Russia had only limited success.
There were prisoner exchanges and moves towards implementing parts of a peace process, known as the Minsk agreements, but no breakthrough. Throughout 2020 his approval rating steadily fell.
There was a notable shift in tone at the Munich Security Conference in February 2022, when Zelensky laid bare the threat his country was facing, and accused the West of appeasing a resurgent Russia.
No Ukrainian leader had spoken so bluntly to the West before, according to Ms Klyuchkovska.
Then, on 24 February 2022 – just hours before Russia first began bombarding Ukraine’s cities – came a key moment.
In a sober address posted on social media, speaking partly in Russian, Zelensky said he had tried to call Vladimir Putin to avert a war, and had been met by silence.
The two countries didn’t need a war, he said, but if Ukrainians came under attack they would defend themselves.
“When you attack us you will see our faces – not our backs, but our faces.”
For his next broadcast after Russia had invaded, he wore military fatigues, reflecting the country’s David-versus-Goliath struggle.
That evening he made another address, warning Western leaders that if they did not help, tomorrow “war will knock on your doors”.
Zelensky’s nightly video addresses became a source of hope and comfort for millions of Ukrainians during the ongoing fighting. His ability to connect was perhaps most evident when he posted a defiant video of himself with several top advisers in Kyiv, after Russia falsely claimed he had fled the capital.
“We are here,” he repeated. “We are in Kyiv. We are protecting Ukraine.”
Zelensky quickly became a national figurehead, with a high of 90% approval ratings in the immediate aftermath of the invasion.