1 Dayawan (Varadarajan Mudaliar)
Kamal Hassan established a new trend with his take of Coppola's 'Godfather'. Soon, Feroz Khan remade the film in Hindi with Vinod Khanna playing the title role. The story for both Mani Ratnam and Feroz Khan's films were inspired from the life of Varadarajan Mudaliar, one of the most powerful men in Mumbai's underworld in the 70s. Together with Haji Mastan and Karim Lala, Varadha bhai founded what is now the Mumbai underworld.
10 Company (Dawood Ibrahim and Chota Rajan)
Ajay Devgn's smouldering presence and Vivek Oberoi's attitude lent the film its panache. But its core strength emanated from one of the greatest rivalries between two infamous dons of the Mumbai underworld – Dawood Ibrahim and Chota Rajan. The bloody gang war sparked by these two rivals left Mumbai shaking. Ramgopal Varma spared nothing in bringing all the blood, gore, and brutality to the screen, and to great success.
2 Vaastav (Chota Rajan)
The real and reel lives of Sanjay Dutt follow an eerily similar track. Mahesh Manjrekar's Vaastav was a tale of a young man who is unwittingly caught in the power struggle of the mafia in Mumbai. Dutt, who had an uncomfortable brush with the law, delivered a convincing performance as the brash Raghu. The inspiration for the film though comes from the rise of Chota Rajan in the criminal class of Mumbai.
3 Once upon a time in Mumbai (Haji Mastan)
Of all the gangsters filmed on screen, Haji Mastan remains the most popular. Style icon,rn Mastan was revered by the poor. Haji Mastan disliked killing for money, and gave as much as he received. No wonder then that Ajay Devgan's portrayal had Haji Mastan written all over it. From the stylish white safaris, to the charitable persona, and the name, Ajay Devgn's character was an homage to one of the most powerful names in Mumbai mafia. Considering the reception, even Mastan would've approved of it.
4 Deewar (Haji Mastan)
It is 1975. A dock worker takes on the system and emerges a hero. This was Amitabh Bachchan at his smouldering best. Yet, even the great man had a benchmark before him. During the filming of Deewar, Amitabh and writer Salim Khan would often visit Mumbai underworld's first don, Haji Mastan. Deewar's Vijay borrowed several mannerisms and styles from the don. It was the first real homage Bollywood had paid to a real life don.
5 Satya (Arun Gawli and Mohan Rawle)
In 1995, Ram Gopal Varma released his film, Satya, which would forever change the way Mumbai and Bollywood looked at its gangsters. The charming Bhiku Mhatre and the serious JD made a lasting impact on audiences. Researching for the film, Ramgopal Varma based his characters on the dreaded dons of Dagdi chawl, Arun Gawli and Mohan Rawale. The inferences were hard to miss in a movie that remains the most popular Mumbai noir film till date.
6 Angaar (Karim Lala and Amar Naik)
Directed by Shashilal Nair, not many people noticed the film in 1992. Its release on cable television and private channels lent it a cult popularity. Powered by performances from Jackie Shroff and Nana Patekar, the film was a take on the gangster Amar Naik and his mentor, Karim Lala. Nana Patekar's performances as the shrewd gangster turned builder earned rave reviews. Kader Khan's powerful dialogues won him the Filmfare Award for the year.
7 Dharmatma (Matka king Ratan Khatri)
Few actors were as talented or as temperamental as Prem Nath. His role as the devout, god-fearing, but powerful gambling boss in Feroz Khan's adaptation of 'The Godfather' put him back on the Bollywood A-list. The inspiration for his role came from the 'Matka king' of Mumbai, Ratan Khatri. It remains one of Prem Nath's most memorable performances on screen.
8 Parinda (Ashwin Naik and Amar Naik)
Vidhu Vinod Chopra's debut film was a mix of shock and awe that thrilled Bollywood to its core. A brilliantly shot film, it captured the imagination of audiences with realistic portrayals of a brutal and subterranean world of crime. Although it did not bear a direct resemblance, the story was parallel to the life of gangster Amar Naik. Amar Naik turned to crime after the attempt on his brother Ashwin's life. Ashwin Naik would soon follow his brother into the underworld.
9 Gangster (Abu Salem and Monica Bedi)
Now here's a film that is almost meta-film about the connection between Bollywood and the underworld. Shiney Ahuja, Emraan Hashmi, and Kangana Ranaut filled in as parts of the love triangle in the movie. The plot was based on the love story of gangster Abu Salem and actress Monica Bedi. Abu Salem was not too pleased with that, and immediately the film was erased of all connections to their real life inspirations. But the public already knew too much.