Wing Chun master Ip Man and his family move to Hong Kong in the mid-1940s after their escape from Japanese-occupied Foshan. There, Ip desires to open a school to propagate his art, as well as make a living during the difficult times, but he has difficulty attracting students due to his lack of reputation in the city. One day, a young man named Wong Leung appears and promptly challenges Ip to a fight, but is easily defeated. Wong leaves humiliated, only to return with some friends to gang up on him. Ip beats them as well. Stunned and impressed by his skills, Wong and his friends become Ip's first students, bringing more disciples to help the school thrive.
Wong is later caught posting promotional posters for the school by some Hung Ga students. One of them challenges Wong to a fight and loses, but his friends take Wong hostage in revenge and demand a ransom from Ip. Ip goes to the local wet market as directed, but the meeting ends in a confrontation with a growing mob of Hung Ga students. Ip and Wong fight their way outside to meet Jin Shanzhao, a martial artist and former bandit, who comes to their rescue with his own gang. The students' master and head of the coalition of Hong Kong martial arts clubs, Hung Chun-nam, arrives to break up the fight. Ip introduces himself, and Hung informs him that before setting up a school, he needs to attend a special fighting ceremony to test his worth. Ip, Wong and Jin are subsequently arrested by Officer Fatso for disturbing the peace but are later released on bail. Hung and Fatso are then shown to be acting as reluctant collectors for the martial arts schools (including Hung's) as part of a protection racket headed by Superintendent Wallace, a corrupt officer in the Hong Kong police.
Ip attends the ceremony and defeats his first challengers, before striking a draw with the last challenger, Hung. Ip is allowed to keep running his school on the condition that he pay his monthly protection fees, but he declines. Hung thus has his students loiter in front of the Wing Chun School and harass anyone interested, causing a street brawl between them and Ip's disciples. Ip is thus forced to close up and move the school nearer to home. Ip soon confronts Hung, who blames him since he wouldn't pay his protection fees, whereas Ip criticizes Hung's management of his students. Hung insists that he is doing what he must and also insists they finish their fight, but during this encounter, Ip stops Hung from accidentally kicking his son as he suddenly appears, earning respect from him. Ip leaves, and the next day, Hung invites him to a British boxing match he has helped to set up, quietly coming to terms with him.
The boxing competition allows for a demonstration by the various martial arts schools to help promote themselves and their Chinese culture. However, the event's star boxer, Taylor "The Twister" Miller, an arrogant, racist and brutal man, openly insults and attacks the students, causing chaos as the masters try to restore order. Hung accepts Twister's challenge to a fight so that he can defend his culture. Although Hung has the upper hand at first due to his wider range of skills, in the second round he suffers a devastating blow that severely disorientates him. As he fights on, he begins to weaken from his asthma and is eventually beaten to death by Twister, as he refuses to concede and allow the man to insult his culture and people. News of Hung's death rapidly spreads throughout the enraged Chinese populace, causing a scandal that spurs Wallace to hold a press conference where he lies that Hung's death was an accident and that he was a weakling who died after a few punches. Twister announces that in order to clear his name he will accept any challenge from the Chinese to participate in a fair, public boxing match, but boasts on that he could kill every Chinese boxer in Hong Kong and that he doubts any of the Chinese are brave enough to face him. Ip Man has already arrived to challenge Twister to a fight.
As his wife goes into labor, Ip finishes training and begins his fight with Twister. Ip exchanges blows with the boxer and seems overwhelmed by the westerner's sheer muscle at first, but begins to make a comeback using his more diverse techniques and great speed. He receives an illegal punch from Twister after the second round's bell, and is also told that kicks would not be allowed due to the judges changing the rules during the match. When it looks like the end, Ip remembers Hung's patriotic spirit and is spurred to go on. He changes his strategy and attacks the boxer's arms to disable him. The fight is brought to a climactic finish as Ip Man rains blow after blow into the knocked-down Twister's face, with flashbacks reflecting the latter's killing of Master Hung. While the Chinese celebrate, Wallace was finally arrested by his superiors for corruption, as Fatso has secretly reported him before the match. Ip then gives a speech to the audience, stating that despite the differences between their race and culture, he wishes for everyone to respect each other regardless of their status. Both the Western and Chinese audience give him a standing ovation while Twister's manager walks away, unhappy at the defeat. Ip goes home and reunites with his family, including his newborn second son, Ip Ching.
A final scene shows Ip being introduced to a boy named Bruce Lee who wishes to study Wing Chun in order to "beat up people [he does not] like". Ip smiles and simply tells the boy to "come back when [he has] grown up".Donnie Yen as Ip Man (葉問), the sole practitioner of the martial art Wing Chun. He arrives in Hong Kong with his family during the 1940s to settle there and set up a Wing Chun school.
Sammo Hung as Hung Chun-nam (洪震南), a Hung Ga master who suffers from asthma. Initially, he is Ip Man's nemesis, but later becomes his friend.
Huang Xiaoming as Wong Leung (黃梁), Ip Man's first student. This character is based on Wong Shun Leung (a Chinese martial artist from Hong Kong who studied wing chun kung fu under Yip Man).
Lynn Hung as Cheung Wing-sing (張永成), Ip Man's wife.
Simon Yam as Chow Ching-chuen (周清泉), Ip Man's friend who appeared in the first movie. He roams the streets of Hong Kong as a beggar with his son.
Darren Shahlavi as Taylor "The Twister" Miler, a British boxing champion. His Chinese nickname is "Whirlwind" (龍捲風).
Li Chak as Ip Chun, Ip Man's son.
Ashton Chen as Tsui Sai-Cheong, Ip Man's student.
Kent Cheng as Fatso (肥波), a police officer under Superintendent Wallace. He is also Hung Chun-nam's close friend. He later becomes disenchanted with his boss.
Dennis To as Cheng Wai-kei (鄭偉基), a gang leader and student of Hung Chun-nam
Ngo Ka-nin as Leung Kan (梁根), the chief editor of a news agency whose father was from the same town as Ip Man.
Louis Fan as Kam Shan-Chau (金山找), a martial artist and robber from the first film who has mended his ways.
Calvin Cheng as Chow Kwong-yiu (周光耀), Chow Ching-chuen's son. He takes care of his disabled father while working at Leung Kan's news agency.
Charles Mayer as Wallace, also a racist man, corrupted police superintendent and Fatso's superior.
Lo Mang as Master Law (羅師傅), a Monkey Kung Fu master.
Fung Hak-on as Master Cheng (鄭師傅), a baguazhang master.
Brian Burrell as the emcee and translator of the match.
Jean Favie as the judge who changed the rules of the match.
Ip Man 2 is the second feature film overall to be based on the life of Ip Man, following the previous film Ip Man. The sequel is the fifth film collaboration between director Wilson Yip and actor Donnie Yen. Ip Man 2 was produced by Raymond Wong and distributed by his company Mandarin Films upon its theatrical release in Hong Kong. It was the last film that Wong will produce under his Mandarin Films production banner. Wong's son, Edmond Wong, returned to write the screenplay. Along with appearing in a supporting role, Sammo Hung reprised his role as the film's martial arts choreographer. Kenji Kawai reprised his role as the film's music composer.
Prior to Ip Man's theatrical release in December 2008, producer Raymond Wong announced plans to develop a sequel to the film. The sequel was intended to focus on the relationship between Ip Man and his most famed disciple Bruce Lee. In March 2009, Wong announced that the Lee character might not appear in the sequel, as producers had not fully finalized negotiations with Lee's descendants on the film rights. In July 2009, it was announced that Ip Man 2 would focus on a young Bruce Lee, prior to Lee becoming Ip Man's most famed disciple. The sequel continues Ip Man's story, focusing on his move to Hong Kong as he attempts to propagate Wing Chun in the region.
Several cast members from Ip Man reprise their respective roles in the sequel. Donnie Yen reprises his role as Ip; Lynn Hung reprises her role as Cheung Wing-sing, Ip's wife, who is now pregnant with their second child. To prepare for her role in the film, Hung asked producers for a 10-pound prosthetic belly to portray the feeling of being pregnant. Hung stated that the difficulty of her role lay in playing someone who goes from "a naive and simple-minded young woman to a strong, understanding and supportive adult." Fan Siu-Wong reprises his role as Jin Shanzhao, Ip's aggressive rival in the first film. In the sequel, Jin attempts to retire from the martial arts world by becoming an ordinary citizen, he later befriends Ip. In a cameo appearance, Simon Yam reprises his role as Ip's friend Chow Ching-chuen, who is now a beggar. Li Chak reprises his role as Ip Chun, Ip and Wing-sing's son.
Sammo Hung was announced as part of the cast in April 2009. Apart from serving as the film's martial arts choreographer, Hung appears as Hung Chun-nam, a master of the southern Chinese martial art of Hung Ga. In August 2009, it was announced that Huang Xiaoming would be playing Wong Leung, a supporting character based on Wong Shun Leung, one of Ip Man's disciples and the person responsible for mentoring Bruce Lee. Former child star Ashton Chen was also announced to be playing a disciple. Veteran actor Kent Cheng also has a supporting role in the film. To Yu-hang, who had a supporting role in the first film, appears in the sequel as a different character named Cheng Wai-kei. Cheng is a gang leader practicing Hung Ga, who decides to exact revenge on Wong after Wong defeats Cheng in a fight. Wilson Yip commented on the casting of the veteran actors as being "a form of tribute to old school kungfu movies."
Yen and Yip reportedly conducted a worldwide casting call for a suitable candidate to play Lee, who is Ip Man's most celebrated disciple. The film briefly portrays Lee at the age of 10. Yip and Yen debated over whether to look for an actor with a solid martial arts foundation or looks. Among the 1300 Mainland Chinese candidates auditioning for the role, Yip narrowed the casting call to two possible candidates: 10-year-old Jiang Dai Yan from Henan and 12-year-old Pan Run Kang from Heilongjiang. On 10 August 2009, it was announced that Jiang Dai Yan would be playing the role of a 10-year-old Bruce Lee. While the Bruce Lee character makes a brief appearance in the film, director Wilson Yip has expressed interest in making a third film that will focus on the relationship between Ip and Lee. Yen, however, has stated his lack of interest in making a third film, feeling that Ip Man 2 will "become a classic."
In November 2008, Yip revealed that there would be another actor appearing in the film, a martial artist who has been a fan of Donnie Yen. Yip commented, "I can only say that he fights even more vehemently than Sammo Hung." However, in February 2010, it was revealed that British actor and stunt performer Darren Shahlavi would have a supporting role as a boxing opponent fighting against Ip Man. Yip later stated that Shahlavi's character "has his own drama. He is also a personage, not just some random foreign guy that appears from nowhere for the sake of getting beaten up, like you see in other films." Other cast members include Ngo Ka-nin and Kelvin Cheng.
The filmmakers stated that while Ip Man was about survival, Ip Man 2 is about living. The sequel is set in Hong Kong in 1949, when the country was under British colonial rule. Screenwriter Edmond Wong stated that the film also "deals with how Hong Kong people were treated under British colonial rule, and Western attitudes concerning Chinese kung fu."
Wilson Yip stated that Ip Man 2 is a much better film than its predecessor in terms of characterization and storyline. The film focuses on disputes between the disciples of Hung Ga and Wing Chun martial arts, as well as the conflict and rivalry of the two practitioners. Wing Chun, as taught by Ip Man, is being viewed as a martial art meant only for girls; Hung Ga, as taught by Hung Chun-nam, is being seen as a macho form of boxing. Of the two characters, Yip commented, "Sammo Hung's character is not exactly villainous, but he's very overbearing, just like his torrential Hung Ga. In contrast, Ip Man is very unassuming, much like his fist." Yip also stated that the film has some moments of "family drama", such as the ongoing conflict between Ip and his wife Wing-Sing.
Prior to filming, a production ceremony for Ip Man 2 was held in Foshan, receiving plenty of media coverage. Principal photography began on 11 August 2009; filming took place in a sound stage at Songjiang Studios in Shanghai. On 28 October 2009, reporters were invited to the set to view the anticipated duel between Donnie Yen and Sammo Hung as it was being filmed. Filming ended on 8 November 2009.
The film's martial arts sequences were choreographed by Sammo Hung, who also worked on the choreography for the first film. Prior to principal photography, Hung had undergone a major cardiac surgery. When he returned to the set, his dramatic scenes in the film were filmed first, with his fight sequences being filmed last. Hung performed his own stunts in the film, which led to him receiving several injuries during filming. While filming a scene, Hung was struck in the face by co-star Darren Shahlavi. He insisted on completing the shoot before going to the hospital. Not wanting his injuries to hinder the production progress, Hung spent five hours trying to complete the scene before going to the hospital for four stitches. After the completion of filming, Hung expressed that he was dissatisfied with the fight sequences involving his character, presumably due to his heart condition. He also stated that he plans to challenge Yen in a future film: "Although I'm the martial arts choreographer, our moves were all rather regulated, being confined by the script. So, I made a pact with Donnie Yen to have a rematch next year if the opportunity arises."
Huang Xiaoming prepared for his role by learning Wing Chun martial arts. He turned his hotel room into a gym, practicing with weights and a wooden dummy. Huang received multiple bruises on his arms, due to his frequent practices on the dummy. Huang would also spend time practicing with the film's stunt team. Wilson Yip praised his performance in the film, stating that Huang "may not be a martial artist, but he specially ordered a wooden dummy, and trained daily at home. In the end, he is doing the action scenes better than Hiroyuki Ikeuchi in the first film."
The Chinese title of the film (traditional Chinese: 葉問2:宗師傳奇; simplified Chinese: 叶问2:宗师传奇) literally means Ip Man 2: Legend of a Grandmaster. The title is a play on the first film's working title which was Grandmaster Ip Man, a title that was changed when Wong Kar-wai clashed with producers while trying to make his own Ip Man biopic. Wilson Yip explained that the title of the film was coincidental rather than intentional: "The sequel is about Ip Man being elevated from a master, a hero to a grandmaster, so we have 'grandmaster' in the title." Wong Kar-wai's film, titled The Grandmaster, was released in January 2013.
Ip Man 2 was released in select Asian countries and in Australia on 29 April 2010. Prior to its release, Mandarin Films publicly launched the film's official website in Beijing on 6 April 2010. The film held a premiere press conference in Beijing on 21 April 2010, only seven days after the 2010 Yushu earthquake. Guests were asked to wear dark-colored clothing in show of mourning; there was a moment of silence for the victims of the disaster. The film's cast, Donnie Yen, Sammo Hung, Huang Xiaoming, Lynn Hung, and Kent Cheng attended the premiere, and donated a total of ¥500,000 (US$73,200) to relief efforts helping in the disaster recovery. The film held private screenings in Chengdu on 21 April 2010, and in China on 27 April 2010, receiving positive reactions from audiences. Mandarin Films has sold North American distribution rights for the film to distributor Well Go USA. Ip Man 2 was released in the United States by Variance Films on 28 January 2011.
In Hong Kong, Ip Man 2 faced competition with the international release of Iron Man 2, which premiered in Hong Kong one day later than Ip Man 2. During its opening weekend, Ip Man 2 grossed HK$13 million (US$1,736,011), surpassing Ip Man's opening weekend gross of HK$4.5 million (US$579,715). The sequel claimed first place at the box office, grossing HK$1 million more than Iron Man 2. The film's revenues decreased by 28.1% in its second weekend, earning HK$9,719,603.56 (US$1,248,996) to remain in first place. The film dropped 45.7% in its third week, bringing in HK$5,293,401 (US$678,613) while still remaining in first place. Ip Man 2 continued to stay at number one at the box office, dropping an additional 39.4% in its fourth week and grossing HK$3,199,567 (US$411,115). During its fifth week, the film moved to fifth place at 79.3%, grossing HK$664,535 (US$85,325). Ip Man 2 grossed HK$43,268,228.72 (US$5,558,704) domestically. The sequel's domestic gross in Hong Kong puts it ahead of Ip Man's total box office gross of HK$25,581,958.69 (US$3,300,847).
Ip Man 2 also broke box office records in Singapore. The film was the highest-grossing Hong Kong film to be released in the country, beating a five-year record held by Kung Fu Hustle. On its opening weekend Ip Man 2 came in second place behind Iron Man 2, grossing SG$1.74 million (US$1,264,919). The film's opening weekend gross surpassed Ip Man's 2008 weekend gross of SG$827,000 (US$463,946).
In total, Ip Man 2 has grossed an estimated US$14,856,127 worldwide during its theatrical run.
Analysts believed that Ip Man 2's box office success was related to the favorable reputation and popularity of its first installment. Huang Qunfei, a general manager of the Chinese theater chain New Film Association Company, made notice of Chinese viewers preferring films made domestically over ones made in Hollywood: "Chinese viewers are less obsessed with Hollywood blockbusters than before. Finally, it is the film's quality that matters. With a good story, local films are likely to win more favor among audiences." Liu Wei of China Daily noted that the film's finale was similar to its competition against Iron Man 2 at the box office: "The hero of Ip Man 2...faces up to a Western boxer and knocks him out. Off screen, it is a similar story."
Analysts also predicted that Mandarin Films' hopes of having the sequel gross over ¥300 million in China was unlikely, due to competition with other films such as Iron Man 2. Another factor was that the illegal recording, downloading and file sharing of the film would cause a potential loss in revenue. A pirated version was released online, one week after the film's release in China, and attracted more than 10 million online users. Raymond Wong publicly expressed that he would be pursuing legal action against the originator of the illegal downloads.
In the first half of the year 2010 (from 1 January to 30 June 2010), Ip Man 2 was the highest grossing Hong Kong film to be released in the country. However, when compared to films produced outside of Asia, the highest-grossing foreign film was Alice in Wonderland with HK$44 million.
Ip Man 2 has a 92% approval rating on Rotten Tomatoes, a review aggregator. Based on 26 reviews, the film currently carries an average rating of 6.8 out of 10.
Singaporean film critic Genevieve Loh of Channel NewsAsia wrote, "Ip Man 2 delivers. Perhaps not as action-packed with dignified choreography as showcased by its excellent predecessor, this installment is nonetheless still exciting, if a tad one-dimensional." James Marsh of Twitch Film praised the film, writing, "Ip Man 2 looks fantastic and does a grand job of evoking the period authentically, lending the film a much-appreciated sense of dramatic gravitas." Joy Fang, a critic for online news portal AsiaOne wrote, "While not as big a movie as the first one, which focuses on heartbreaking and intense issues arising from the Japanese occupation in China, this film evokes Chinese pride with its strong cultural roots." Ho Yi, of the Taipei Times wrote, "Despite its plot holes, the Ip Man series has potential and recalls the 1990s' Once Upon a Time in China franchise starring Jet Li." Amir Hafizi of The Malay Mail praised Sammo Hung's martial arts choreography: "With fluid movements intricate interplay between contrasting martial styles and gorgeous sequences, kung fu fans will definitely get their eye-balls' worth here as this time around, the introduction of Western boxing into the mix makes for some interesting choreography." Roger Ebert of the Chicago Sun-Times awarded Ip Man 2 three stars out of four, writing, "In its direct and sincere approach, it's a rebuke to the frenzied editing that reduces so many recent action movies into incomprehensible confusion."
Darcy Paquet of Screen Daily had mixed opinions of the film. He wrote that the film's performances and fight sequences "should ensure decent theatrical runs." Paquet concluded his review by writing, "Ultimately, the film's energy and humour overcome cartoonishly bad performances from the British actors and an utter lack of surprises in the final two reels." Amanda Foo of The UrbanWire awarded the film two stars out of five, writing in her review, "It's no surprise that Donnie Yen isn't willing to sign up for any more Ip Man movies, with the shameless repetition that is happening in these films, even the most ardent fan would be tired." Matt Prigge of Metro New York stated in 2016, "There are gobs of films about Ip Man [...] Of these, the three films starring Donnie Yen are the trashiest; the second one is basically a remake of Rocky IV."
In Hong Kong, Ip Man 2 was released on DVD, and Blu-ray Disc formats on 25 June 2010. Releases include a single-disc edition and a two-disc special edition on DVD Features for the special edition DVD, as well as the Blu-ray disc, include deleted scenes, several theatrical trailers, cast and crew interviews, a making-of featurette, coverage of the film's gala premiere, and a shooting diary.
Coinciding with the sequel's home video release, both Ip Man and Ip Man 2 were released as a double feature on DVD and Blu-ray Disc. Releases include two-disc special editions of both feature films with a total of four discs on DVD, as well as a standard DVD edition featuring both films with a total of two discs.
The third installment began filming in 2015. Edmond Wong, Raymond Wong and Wilson Yip returns as screenwriter, producer and director again, respectively. Donnie Yen reprises his role as "Ip Man". In March 2015, The Hollywood Reporter announced that principal photography began; they also revealed that Mike Tyson has been cast in a role and Bruce Lee is portrayed by Danny Chan, reprising the role from The Legend of Bruce Lee.