Now, in a very serious time for the world, he is the president of his country and an image of strength against the Russian invasion.
"It's not surprising that he would appear to have the heart of a lion because the Ukrainian people are the same way," said David Dodson who has known and worked with Zelensky for 14 years.
In that time, he says they've become friends and he calls him by the familiar version of his name: Volodya. Dodson directed him in three feature films, including Zelensky's last movie "Me You He She."
Dodson says he always saw leadership qualities in the the now Ukrainian president.
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"He's sincere, he actually means it. There's no guile, he's not overwhelming anybody with ego, he just genuinely cares," he added.
The images of Zelensky holding news conferences and showing himself live in his office are startling considering he is undoubtedly a target.
"In the same way that if somebody were to break into your home you would have no choice but to stay and defend the things that you loved and he's doing no different."
While they made movies together Dobson says fans would come up and ask Zelensky for photos and autographs and he would always take time for them. He says that how he was with everyone - always making them feel part of the family.
"That's a very Ukrainian kind of quality, everything becomes about family very quickly and so the feeling of trust is the thing which gives you power, and I know that the Ukrainian people now, in this moment, trust him and that gives them the courage to go on," he said.