Ip Man is now world famous for his portrayal by Donnie Yen in the eponymous film series. Prior to that, Ip Man was best known as Bruce Lee's Wing Chun Sifu in Hong Kong, before Bruce made his fateful journey to San Francisco in 1959.

Ip Man was born in 1893 in Futsan, a city in the Guangdong province of China.  As a twelve year old boy, Ip Man started watching a kung fu class that had moved into the Ip Family Hall in downtown Fatsan.  The teacher was the famous Wing Chun master Chan Wah Shun, who was the disciple of the legendary Leung Jan (佛山贊先生), who is regarded as a folk hero. 

Young Ip man wanted to join the school.  Chan Wah Shun disliked taking wealthy students, finding them lazy and ill suited for the rigors of training Wing Chun.  Instead of refusing outright, he instead asked the young boy for a small fortune in silver as tuition.  After a time, the young Ip Man returned with the tuition fee, which was provided as a gift by his mother.  Reluctantly, the master opened his doors. Ip Man was the last pupil he would ever accept.

Ip Man studied closely under Master Chan for three years until he passed away. (Much later, Ip Man continued his tutelage under the elder student Ng Chun So.) The Ip Family moved to Hong Kong in 1908.  The Ip family was wealthy, and as young man, he attended the prestigious St. Stephens college, receiving a Western education. 

China was a failed state, occupied by foreign powers.  Stripped of it's wealth, China was flooded with opium, used as an economic weapon to destablize the country and turn it's people into addicts.  The Qing government suffered a series of defeats most notably, the Taiping Rebellion, which killed ~30 million people.

In 1911, the Xinhai Revolution brought about the fall of the Qing Dynasty.  Sun Yat Sen' KMT, attempted to unify China into a Democratic state, governed by the people, under a rule of law, but this stalled and the fate of the country was uncertain. 

In Hong Kong, attending St. Stephen's college, a 17 year old Ip Man witnessed a policeman beating a Chinese girl in public.  This was an Indian offficer, from the British Commonwealth government.  Ip Man and his friends, being teenagers from unoccupied Futsan, unwisely protested the mistreatment of the girl.  The policeman swung at Ip Man, who quickly defended himself, knocking the policeman to the ground with a single punch.  Word of this incident got around, and It's said this was the basis for his meeting his third teacher in Wing Chun, Leung Bik, the son of Leung Jan. Ip Man studied with Leung Bik until he died in 1913. 

Returning to Futsan the following year, Ip Man's fighting skill was challenged by other Gung Fu masters, and he emerged the winner of these contests.  His reputation quickly spread.  World War Two began in 1937, when the Japanese invaded China life became much harder.  The Communists stole Ip Man's family's wealth and he was forced to find work to live. Luckily, his reputation as a fighter made him a popular candidate as a senior policeman in the KMT government.    There are a few famous stories of Ip Man's fights during this time.

One event involved a newly recruited police officer, waving his revolver around and intimidating civilians.  Ip Man, unknown to the new recruit and wearing traditional Chinese clothing, was not recognized by the enraged officer.  Ip Man quickly siezed the officer's revolver, disarming him and in the process knocking the cylinder out.

During another incident, while working to apprehend a known criminal named Tsu Ping, Ip Man spotted a man fitting the description, and wanting to avoid a gunfight in a crowded street, Ip Man told his his men to stay back.  Ip approached the suspicious character alone.  Ip Man called out his name, and the suspect pulled a concealed revolver.  Moving quickly, Ip Man seized the suspect, and he was disarmed, restrained and taken into custody without  incident.

Returning the the police station, Tsu Ping complained loudly about how Ip Man had surprised him, and in a fair fight, Ip Man wouldn't have a chance.  Ip Man, decided to take him up on his offer.  Tsu Ping's restraints were removed and they squared off for a fist fight.  Tsu Ping swung widely, and Ip Man kept his distance.  Spotting an opportunity from an overextended punch, Ip Man grabbed Tsu Ping's arm, and quickly pulled him down, into a knee strike to the man's chest.  With that single strike, the much larger Tsu Ping collapsed, frothing at the mouth. That firmly established Ip Man's reputation in Futsan and he was later promoted to captain of the detective squad.

Ip Man's career as a police officer had began around the same time as WWII.  The war ended with Japanese capitulation in 1945, but was completely devastating to China, which suffered some 20 million casualties. 

After WWII, Ip Man served in the KMT military, before returning to duty in the Futsan police as Captain in charge of patrols in Namhoi district.

Immediately afterwards the Chinese Civil War began, and within four years the Chinese Communists (PRC), having sat out the majority of the war, defeated the beleagured KMT, who had been worn down from extended battle with the Japanese.  Free China was abandoned by it's western allies. The Civil War cost China another 8 million casualties and ended with the Communists taking control, and the KMT fleeing to Taiwan.

In 1945, Ip Man fled to Hong Kong to escape Communist persecution, leaving behind his family in the process.  At that time, the Communist party would have likely imprisoned Ip Man, or worse, for his collaboration with the Nationalist Chinese government.

It is important to note that 17 years later, during the Cultural Revolution, Communists imprisoned and executed martial artists to totally break the spirit of the Chinese people.  A few years earlier, Mao Zedong's so-called "Great Leap Forward" had killed some 45 million people.  The Chinese, enduring a period of nearly continual war for over a hundred years, were repeatedly conquered.  At the end of the civil war, they were already and totally disarmed of firearms.  After killing his political rivals and purging the military, Mao sought a means to ensure that the Chinese people would never be able to rise against him, and wouldn't even have access to hand-to-hand fighting.  Killing the Kung Fu Masters was a way of ensuring total control.

In Hong Kong, for the next thirty years, Ip Man worked as a martial arts instructor. It was here at this school in Hong Kong that Grandmaster Chan and Bruce Lee became his students. Although he was not the most senior Wing Chun expert in Hong Kong, and never claimed the title himself, he was regarded by many as the head of the Wing Chun style in Hong Kong.

Perhaps after being asked  an inappropriate question by a doubting student, Ip Man said, that if a student of his, who had mastered the fighting concepts of Chum Kiu lost a fight, that he would throw himself off the rooftop. 

Ip Man was an outspoken and critical teacher at times, and once said that any student of his who refused to accept a challenge fight would be kicked out of the school.  His martial arts school gained widespread notoriety in many bare-knuckle challenge matches, often held on roof tops.  Ip Man's training produced successful fighters such as Wong Shun Leung, who was .   These fights were chronicled by local reporters, and one of Chris Chan's seniors, a man named Wong Shun Leung, was an undefeated champion of these challenge fights. 

Chris Chan, at the age of 15, in the year of 1955, witnessed a rooftop match with one of Ip Man's Wing Chun fighters.  When he saw the fight, he knew wanted to learn Wing Chun.  in 1956 year, Chris Chan joined Ip Man's school.  Bruce Lee was also training at that time and the two became friends and rivals. 

Even at age seventy, Great Grandmaster Ip Man had the strength of a young man. One night, while taking a walk, he was attacked by two young men. Using the pak sao technique, Great Grandmaster knocked one knife away and kicked the man backwards. Without a second of hesitation, Great Grandmaster Ip Man also kicked the other man, skillfully defending himself against two men nearly fifty years younger than him.
 

Similar to Master Chan Wah Shun, Great Grandmaster Ip Man was very selective of his students, saying, “No doubt it is difficult for a disciple to select a teacher, but it is even more difficult for a teacher to select a disciple.” Through his dedication and hard work, Wing Chun Kung Fu has been preserved in its simplicity, practicality, and beauty. Because of Great Grandmaster Ip Man, students now have the opportunity to learn what used to be one of the most secret arts of China.

Although he was the first Wing Chun teacher to have an open school, he only did so because he was forced to do so in order to survive. In 1965, after becoming a famous movie star, Bruce Lee returned to Hong Kong to try to convince Ip Man to let himself be filmed, and Ip Man refused.  It was only a few days before his death, that Ip Man decided to film himself performing the Wing Chun system.  He used his last bit of strength to demonstrate the Siu Nim Tao, Chum Kiu and Mook Yan Jong forms he learned as a young boy from Chan Wah Shun.