Following his success in television productions, Director Neo took on new challenges and ventured into the film industry in 1998 with Money No Enough (1998), Singapore’s 3rd highest grossing feature (2012), Ah Boys To Men (2012), Ah Boys To Men 2 (2013) which is Singapore’s highest grossing feature film to-date, and many more.< film to-date. Consequently, he scripted, directed and produced a successful string of coveted movies namely I Not Stupid (2002) and Homerun (2003).
Besides garnering record high box office earnings, Jack Neo’s later works drew much regional and International attention. Among his well-commented works, Homerun (2003) won the first international movie award for Singapore. A total of Singapore’s media industry, Jack Neo was awarded the Lifetime Achievement Award in 1999 and Multi-Talent Award in 2004 from MediaCorp Singapore in the six international awards were honoured to the movie including the International Kids Film Festival Of Home Iran 2003’s “Best Director" title. In recognition of his achievements and contributions towards Singapore Star Awards. He also received the Public Service Medal Award in August 2004 and the Arts Cultural Medallion Award in October 2005.
In 2016, to celebrate Singapore celebrate Singapore’s 50th anniversary, Jack shot Long Long Time Ago 1 & 2, with a budget of SGD$5 million for both parts of the film. The movies’s 50th anniversary accurately depict the hard life of Singaporeans in the early days. In 2017, he released the fourth installment of Ah Boys to Men in celebration, Jack shot Long Long Time Ago 1 & 2, with a budget of SGD$5 million for both parts of the film. The movies accurately depict of 50 years of military national service in Singapore.