To’s father, a gambling addict, left the family when he was young, but he followed in his father’s footsteps anyway and became a gambler at the age of 17. To escape from loan sharks chasing him, To fled to Taiwan; he returned to Hong Kong when he was 22, and started working in construction.

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While working on a house, To met a TV producer who remarked on his talkativeness and encouraged him to audition for acting roles. After landing a contract with ATV, To began appearing in a variety of soap operas.

To eventually moved on to big-screen roles, and one of his best known performances was in the now classic 2002 film Infernal Affairs, in which To played Tsui Wai-keung, the slow-witted but fiercely loyal henchman of a triad boss.

To was also credited as a producer of Isabella. The actor had begun venturing into producing after taking the advice of fellow actor Kent Cheng Juk-si.

“[He] told me, ‘Hey, you need a goal’. And I had none. He suggested that I produce,” To recalled in 2007. “He told me to watch a movie 50 times – watch my own part, then the other actors, then the supporting cast. Then the camera work, then lighting, then costumes, artwork. And then listen to the soundtrack.

“I’m more into producing now because as an actor you’re forced to be passive – you stay at home waiting for agents to call, and end up playing Wii all day.”

But To never gave up acting, appearing in a string of comic films – some of which were memorably dirty-minded and vulgar – throughout the 2010s.

These include La Comédie Humaine, in which To plays a hitman from China who befriends a screenwriter (Wong Cho-lam). To’s appearance – alongside co-director Chan Hing-ka – at a public screening of the film in June 2010 started the trend of meet-the-audience sessions at commercial screenings that has since become the norm for the Hong Kong film business.

The actor’s propensity for comedy can be viewed as an extension of his personality. “All my characters are the same,” he told the Post in 2014. “There’s no difference between any of them. They’re all me … All I’ve wanted is to make more comedies. I haven’t made any non-comedy for years, and I have no intention of turning back now.”

Aside from acting and producing, To is known for his outspoken political views. In 2014, he was vocal in support of the “sunflower” student movement in Taiwan and the Occupy Central protests in Hong Kong.

During the latter, he got into heated online exchanges with Chinese internet users and openly criticised the Chinese Communist Party. His stance led to a boycott of his films by audiences in China, and To soon lost his footing in the Hong Kong and Chinese film markets after production companies refused to work with him.

As a result, from 2015 onwards, To partly shifted his focus to the Malaysian and Singaporean market, starring in films like the Lunar New Year comedy King of Mahjong (2015) and Let’s Eat! (2016, which he also directed).

The channel has over 677,000 subscribers on YouTube and 901,000 followers on Instagram. Hong Kong television actress Kristal Tin Yui-lee, whom To married in 2005, frequently appears on the show as a co-host.

To is now based primarily in Taiwan, having moved there in 2020, and became a naturalised Taiwanese citizen in 2022. He frequently attracts tens of thousands of likes for the hot takes posted on his Facebook page.