He had furiously rebelled against Singapore's strict censorship policies, even producing a short film, "Cut" that mocked the system, but these days he gets invited to give talks in schools and work on government projects.
The award-winning Singaporean film director, Royston Tan, known for his bold portrayal of social realities, seems to have come of age, and so too has the wealthy city-state he grew up in that has formed the landscape and backdrop of his films.
"In the past, we would throw things at each other, but right now we can sit down and have a cup of coffee and talk about our differences," the 41-year-old said in a recent interview with Kyodo News.
"I realize that I have grown, I am still a rebel. I just rebel in different ways."
Reminiscing on the past, especially those early years of constant clashes with the censors, Tan said Japan occupies a special place in his heart.
"Japan has played a very, very big part in my life," he said, recalling how he spent two months in the northern Japanese city of Sapporo in 2004 for an artist-in-residence program.
Back then, Tan was in his early 20s and had been ruffling feathers at home with his very short musical comedy "Cut" that rapped the censors. It appeared soon after his first feature film "15" about teenage gangsters, which was subjected to a record-breaking 27 cuts.
Japan, he said, "was a refreshing journey for me because after I came back, my style had changed."
In Sapporo, "Not many people spoke English and I realized that I had to use the most basic words to communicate. As a result of this, I realized the beauty of not talking. We communicated with just eyes, a little bit of body language."
It was there he wrote his feature film "4:30," which was co-produced by Japan's national broadcaster NHK and released in 2005. It is about a young boy who wakes up at 4:30 a.m. daily to spy on a suicidal Korean tenant of his family apartment.
In the film, "nobody talks," he said.
"We have a universal language, which is the language of the eyes. That's what I really learned (in Japan)."
Communication between people who speak different languages again emerged in his more recent film, "Bunga Sayang," which clinched the Best Asian Short Film prize at the Sapporo International Short Film Festival and Market in 2016.
Part of the award-winning anthology of seven short stories directed by a like number of local directors to celebrate Singapore's 50th anniversary, the story is about a young Chinese boy who strikes up a friendship with an old Malay woman living next door. When his tap runs dry mid-shower, the boy goes over to his neighbor's house for water.
Deceptively simple on the surface, the film can be seen as tackling a pertinent and delicate issue of multiracial relations.
As far back as 2001, the Short Shorts Film Festival & Asia, an annual international short film festival in Tokyo, had introduced his film "Sons" when it began screening Asian films and continued to give him more such international exposure over the years.
"The Tokyo Short Shorts has been the very first festival I have been to in Japan, and usually the first experience...you will never forget," he said, adding that he would love to revisit "the magical feeling in Tokyo."
Giving a glimpse of his next film, he said, "I feel that it's very important after I cross the 40-years-old mark to have a reunion with all the important milestones, the people who made an impact in my life through my film."
After the turbulence of the early years, Tan's icy relationship with the authorities seems to have thawed.
These days, he gets invited by the National Arts Council to schools to give talks about his films and to reach out to teenagers. He has also been involved in video productions for government projects.
The film scene in Singapore is still tightly regulated.
All films shown here have to be submitted to the Board of Film Censors for classification, and those deemed obscene or party politics, or regarded as undermining national security can be banned.
Local filmmaker Tan Pin Pin's film "To Singapore, With Love", about Singapore's political exiles, was banned in 2014.
However, Tan feels that there is now more space.
"Apart from religion and politics, there is a wider range of things that we can talk about now."
"If a certain decision is being made, they will have a dialogue with us to tell what are their concerns, and they listen to us. In the past, it was not a two-way communication. So I feel that this is a huge improvement."
For example, in recent months the public has been consulted on the government's plan to amend the Films Act, although some aspects of the proposed amendments have raised concerns among film industry professionals here.
Tan was among dozens of them who signed a position paper last December expressing concern about the proposed amendments, such as those to give expanded powers to film classification or licensing officers in investigating breaches of the act.
Amid the lack of freedom of speech in the city-state where street protests are limited to a so-called Speakers' Corner in a small public park, Tan is keenly aware that as a filmmaker, he can at least implicitly protest in his film.
"At least for me, I have my protest inside my films, I realize that I can address my concerns for Singapore through my films."
"Back then, it was very blunt, but now I think I know how to express it in a careful way -- and it's still a very effective way."
He said his next film will be shot in Phuket, Thailand, as an international production with a cast that includes Japanese, Thai and Taiwanese actors.
"It's the first time I am moving out of Singapore to do something very different," he said, "It will be about forgiveness."