Born into extreme poverty in south London to a deadbeat dad and a mentally ill mother, spottily educated little Chaplin spent his childhood as a clog dancer, in and out of workhouses and relatives’ homes, before becoming one of the most famous personalities in the world by the age of 26. For the major part of his life, he lived in a world where people worshipped him, admired his artistic works and despite he looked nothing like the ideal prince charming with his height of only 5’5 inches, women would throw themselves at him. However, he never respected any woman and although he was aware of his actions and the consequent heartbreaks of his partners, he used and discarded his lovers indiscriminately and never stopped falling for young girls.

He would frequently boast about his sexual conquests, his sexual encounters with Hollywood actresses and would even take pride in telling people that he has slept with around 2000 women. Even though his boast sounds obnoxious, all those women endured the brunt of Chaplin's selfish and cruel personality and he was aware of that.

Considered a living legend, Chaplin preferred young girls and one of the first women to experience this strange obsession of the man was Edna Purviance, a 19-year-old actress who responded to his advertisement for the prettiest girl in California to play a role in a moving picture. Despite Chaplin’s concern that she might be too serious for comedic roles, Edna won the role of the leading lady in A Night Out (1915) and soon enough they became more than just co-stars. She appeared in 33 of Chaplin's productions, including The Kid (1921), but finally became tired and disgusted as she could not find a place in his overly packed work schedule.

His dedication to work eclipsed the attention he paid to his lover, even he did not have the time or did not care to write to her, while he was in New York. Eventually, she drifted apart and started seeing another man.

Next in the line was 16-year-old Mildred Harris, who met Charles Chaplin at a party early in 1918 and made a deliberate attempt to make herself noticed by Chaplin, one of the most eligible bachelors, young, smart, single and already a successful man..Obsessed with young women, Chaplin could not overlook her beauty and after the first meeting, they dated for several months. Despite the rumours of their marriage and their continued denial, they did marry quietly on 23 October 1918, based on a false alarm by Mildred that she was pregnant, but she was not. She simply cheated Chaplin to get married without delay. As Mrs. Chaplin, Mildred was showered with lots of new film contracts, but it adversely affected Chaplin’s work. He had problems to properly adjust his new married life, felt she was not his intellectual equal, while Mildred found problems with Chaplin's workaholic nature.

His frequent affairs also made Mildred’s mental health worse.Their son, Norman Spencer Chaplin, was born on 7 July 1919, but the child survived only three days. It was during the production of The Kid that the marriage fell apart and the couple divorced on 13 November1920, just before the release of the film in early February 1921. However, the film was edited in a room at the Hotel Utah, as Mildred Harris sought to attach Chaplin's assets during the proceedings of the divorce and the raw negative of the film was smuggled to Salt Lake City.

Lillita Louise McMurray, better known as Lita Grey, first met Chaplin at a very young age, while she was at a restaurant with her mother. Her mother spotted Chaplin, while he was in the restaurant with his crew on a lunch break and she introduced themselves. She was introduced to Chaplin for the second timeby Charles Riesner, one of the neighbours of the McMurray family and Chaplin's assistant director, during the making of The Kid in 1920. As the fruitful outcome of the meeting, Lita played the role of Edna’s maid in The Idle Class (1921), along with her mother in the same film. In addition to that, she also played the role of the flirtatious angel meeting the Tramp at ‘Price is Love’ in The Kid. However, she caught Chaplin’s eye in 1924, during the preparation of The Gold Rush (1925), when he was desperately searching for a new leading lady to replace Edna Purviance and strongly felt that she would be the ideal choice for the dance hall girl in his next film. Immediately, he got her signed a contract in March of 1924, gave her a new stage name Lita Grey, filmed several scenes in The Gold Rush and even she travelled with the cast to Truckee, California for location shooting. However, during the trip, she was impregnated by the then-thirty-five-year-old Chaplin.

To avoid the prospect of domestic responsibility, Charlie suggested an abortion, which was bluntly rejected by her catholic mother. As his last suggestion to get her married to a willing young man, with a dowry of $20,000, was also rejected, Chaplin had to marry the 16-year-old Lita secretly on 26 November 1924 in Mexico, to avoid scandal and imprisonment for having sexual relations with a minor. But immediately after the marriage, he left his wife to go out fishing, but trapped himself into a second unhappy marriage. It is said that, on their train back to California, Chaplin suggested Lita jump off the train to end her misery.

The conjugal life of Charles and Lita was doomed to fail from the inception, as there were few common interests between the two.However, although Chaplin did not like his wife, according to Lita, he remained a human sex-machine. Finally, she headed for the divorce, alleging Chaplin was about to pull a gun at herand threatened abortion. The rocky marriage turned into a long, nasty public divorce in late November of 1927, when it was alleged in the divorce papers that Lita was forced to perform sexual acts that were pornographic and illegal in California and was also compelled to take part in a threesome with another woman. During the proceedings, Lita’s lawyers also threatened to reveal the names of six actresses who Chaplin slept with after the marriage. Finally, at the end of the bitter legal battle, the judge awarded Grey the world’s then-largest divorce settlement.

Born on 3 June 1910, Pauline Levy or Marion Levy, better known as Paulette Goddard, met Charlie in 1932, at a party thrown by a friend of Chaplin. Soon they became intimate friends and almost instantly the intimacy of friendship developed into a hot romance. Charlie bought a yacht during this period, and the couple used to entertain friends on cruises often on weekends and holidays. During that time, Chaplin’s keen eyes could see Paulette as his perfect Gamine in his new film, Modern Times (1936) and Paulette’s first major film role in the film instantly made her a star.

It is said that they got married while they were travelling to the Orient after the release of the film, which was not verified by anybody. However, it was a happy union during that early part of their relationship in the 1930's, when once Lita Grey Chaplin and Paulette accidentally met at a birthday party and they got along fine. Even, Lita expressed her pleasure to see Paulette in Charlie’s life.

However, during the filming of The Great Dictator (1940), Paulette's last film with Charlie, the friends around the couple could feel the relationship was failing, they were steadily drifting apart. One of the primary reasons for their separation was Chaplin’s ill-treatment and bullying of her on the sets. He always tended to control her on the set, telling people how he had to teach her things about acting and his remarks would leave her all crying.At that time, Paulette was having a romantic involvement with George Gershwin, while Chaplin was busy with comedienne Thelma Todd. Finally, instead of enduring the bullying on the sets, she left him in 1940 and they were divorced on 4 June 1942.

Oona O' Neill, born in 1925 to Nobel and Pulitzer Prize winner famous American playwright Eugene O’Neill and English-born writer Agnes Boulton, was introduced to Chaplin through film agent Minna Wallace, in the fall of 1942, when he was looking for a new face to play the leading lady for his proposed new film 'Shadow and Substance'. Chaplin found Oona beautiful, but too young for the role. However, due to the continuous persistence of the girl and Wallace, Chaplin finally agreed to give her a film contract, which changed the life of the two concerned souls.

Although the project of filming Shadow and Substance was shelved, the relationship between Chaplin and O’Neill developed from professional to romantic. Initially, Chaplin had been reportedly shy about involving himself with yet another young girl, but the deep involvement of Oona O’Neill made it easy for him to take the decision. On 16 June 1943, a month after O’Neill had turned 18, the couple eloped and quietly married in Santa Barbara, California, while the 36-year gap between the two received a large amount of media attention and caused a social scandal. However, even with the age difference, the couple had a special bond that would last a lifetime and they remained married until Chaplin died in 1977.