According to Felix Chong's Once a Gangster, being a gangster in real life is nothing like being one in the movies. Chong, who co-wrote the Infernal Affairs series, reportedly got the idea for the film after talking to real-life triad members who complained that Johnnie To's Election films actually don't reflect how the triad really is today. According to them, no one wants to be the boss anymore because there's no benefit to being so.

With that idea, Chong created a story where the central conflict is about two men fighting each other to not become a gang boss. Designed as a reversal of the popular genre, Chong even cast Jordan Chan and Ekin Cheng - stars of the Young and Dangerous series, considered the definitive representative of 90s triad movies - to play the film's two aspiring non-leaders.

As the stars of the series, the two men were the symbols of the genre's popularity in 90s Hong Kong pop culture, making them also the main targets of criticism by cultural critics that accused them of corrupting Hong Kong youths. A decade later, the two get their chance at redemption by playing two men who have better plans than leading a gang. The title of the film itself carries plenty of ambiguity - is it a phrase that's followed by "always a gangster", or does it mean that its characters can shed their lifelong gangster identity?

From the out-of-touch elders that still believe running a triad is a desirable job to the undercover cop whose real identity is a secret to no one (based on a real character, according to Chong), Once a Gangster is designed as a total reversal of the popular triad films of the 1990s. No triad film cliche is left unscathed in Chong's parody, including the ones in his own Infernal Affairs series. Chong's comedic style leans on the absurd, with people making seemingly real choices within the film's hyper-reality. Despite Chong's uneven direction (it's his first solo directorial effort), he has delivered a film that is both thoughtful and endlessly amusing, thanks to a script that balances absurd comedy with serious dilemmas. However, Chong lets his film become too uneven at times, presenting seriously bloody violence that is presented a little too lightly for comfort.

The lighthearted approach to violence may also come from the fact that Chong's triad saga isn't intended to only be what it appears to be. In addition to being a genre parody, the mini gang war Chong creates can also be read as a parallel to contemporary Hong Kong politics. At one point, a character complains aloud that the triad election system is an unfair "small circle election", a reference to the existing electoral system in Hong Kong that allows only an exclusive committee of 800 people to vote for the Chief Executive. Also, the protagonists' unwillingness to take the job of the leader reflects a general attitude that the job of the Chief Executive is not only an undesirable one, but one that means very little in reality. In the days of Chinese-Hong Kong co-productions that force filmmakers to appeal to Mainland Chinese sensibilities, Once a Gangster is a rare true Hong Kong film that should be appreciated by any Hong Kong film fan.