As a model, Cheng was featured in several music videos, including one of Heavenly King Jacky Cheung’s. In 2003, he took on the role of the second male lead in The Rose, a Taiwanese drama serial which also starred Taiwanese girl band S.H.E. and renowned actress Cecilia Yip. It was this role that kick-started his acting career. Following his rising popularity and the success of his first acting role, Cheng was asked to make a guest appearance as Lucifer in Taiwanese boyband Energy’s first-ever idol drama, Dance with Michael, in the same year. Cheng starred as the main lead in two dramas, Nine-ball and Magic Ring in 2004. Although these two serials achieved lukewarm success, Cheng took the role of the main lead in It Started with a Kiss in the following year. This serial achieved high ratings in Taiwan and was popular with audiences throughout Asia. Cheng’s popularity rose tremendously as a result. It Started with a Kiss was also Cheng’s first collaboration with actress Ariel Lin. The two, who are often touted as one of Taiwan’s most compatible on-screen couples, paired up again in the 2007 sequel to It Started with a Kiss, They Kiss Again; as well as Love or Bread (2008) which is unrelated to the Kiss series. Cheng has starred in numerous drama serials produced in Taiwan,China and Japan, but remains most well known for his roles in The Rose and the Kiss series.

Excluding drama serial memorabilia, Cheng has released three pictorial books in addition to four calendars and one mini pictorial in conjunction with the release of his EP in 2009. He has also authored two books and co-authored another on his hometown Taichung. He was also featured in a 2006 book on Catwalk Modelling Agency. Cheng has won multiple awards as a model and as a performing artiste. The most notable include one at the Asia Model Festival Awards 2009, in which he won the Asia Special Award. Cheng, together with Sylvia Chang and Mike He, was appointed as an ambassador for World Vision in December 2009.

2009 was a quiet year for the television star, who spent the year busy with his theatre debut, Design for Living, starring opposite stage veterans Sylvia Chang and David Wang, under the directorship of Hong Kong stage director Edward Lam. The troupe made several sell-out shows in Hong Kong, China, Taiwan and Singapore. Cheng said that it has always been one of his goals to star in a stage play and was very honoured to have been able to star in the same production as Sylvia Chang. In the same year he also released his first EP, Sing a Song. Cheng is known by his friends in the industry as one who loves to sing. Album sales were fair and the EP topped certain charts in Taiwan but Cheng failed to convince music critics of the industry. Much to the dismay of his fans, Cheng did not star in any drama series in 2009.

In addition to his entertainment career, Cheng is completing his part-time university studies in tourism management at Hsing Wu College. As all males in Taiwan have to enlist for National Service, Cheng is due to enlist as soon as he completes his education. In 2010 Cheng represented Taiwan and performed at the 7th Asia Song Festival, organised by Korea Foundation for International Culture Exchange, at the Seoul Olympic Stadium.