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Yen had a starring role in the film Iron Monkey in 1993.Yen and Li appeared together again in the 2002 film, Hero, where Yen played a spear (or qiang) fighter who fought with Li's character, an unnamed swordsman.Yen also worked as action choreographer in Stormbreaker, starring Alex Pettyfer.Yen continued to work with Wilson Yip in Flash Point (2007), in which he starred as the lead character and served as producer and action choreographer for the film.In August 2011, while Yen was on a vacation with his family in the United States, he reportedly received an invitation by producer Avi Lerner to star in The Expendables 2.It was stated that Yen was considering the offer, had many films at hand, and would wait until deciding whether the script appealed to him.He won the award for Best Action Choreography at the Golden Horse Film Awards and the Hong Kong Film Awards for his performance in Flash Point.
Yen continued to be active in Hong Kong cinema in the 2000s, starring as Chu Zhaonan in Tsui Hark's wuxia epic film Seven Swords, and as Ma Kwun in Wilson Yip's brutal crime drama film SPL: Sha Po Lang in 2005.
Seen as one of the most popular film stars in Asia of the early 2000s, Yen was one of the highest paid actors in Asia in 2009.
He played Wing Chun grandmaster Ip Man in the 2008 film Ip Man, which was a box office success.
Both films were featured at the 2005 Toronto International Film Festival.
Later that year, Yen co-starred with Nicholas Tse and Shawn Yue in Wilson Yip's Dragon Tiger Gate, an adaptation of Wong Yuk-long's manhua series Oriental Heroes.