During the late 1990s to early 2000s, he was best known for his role as Jacky Chang aka Ah Bee, a salesman with a penchant for grabbing 'lobangs' (good opportunities that cannot be missed) in the popular Channel 8 sitcom Don't Worry, Be Happy, which spanned for six seasons.
Chew initially dropped out from the role of Ah Bee after the 3rd season due to fear of being typecast, and also because he wanted to focus more on drama and variety shows.
He eventually reprised the role for the latter half of the 6th (and final) season for Don't Worry Be Happy, and appeared in a spinoff series Lobang King focusing on Ah Bee and his new league of friends.
In 2009 he won the Best Supporting Actor award, despite the nominations being dominated by cast of the popular blockbuster series The Little Nyonya, for his portrayal of a promising young doctor driven to vice and insanity by unfortunate circumstances in The Golden Path.
Now a well-known household name, Chew has gone from acting in drama series to hosting shows and large-scale events including overseas collaborations with Taiwan and China.
He revealed during a celebrity talk show in early 2008 that he did not have a happy childhood, often being abused by his overly strict father (a compulsive gambler and alcoholic), who committed suicide when Chew was still in primary school.
[8] On 19 December 2008, Chew announced during a church event that he was suffering from Kennedy's disease, a muscular dystrophy illness that resulted in him limping while filming for his latest role as Wang Zhongkun in Love Blossoms II.
[12] In September 2016, Chew appeared in episode 6 of I Want to Be a Star that had to be taken down from Toggle's website due to public outcry about the show's casual racism.