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Akshaye Khanna, Emraan Hashmi, Ajay Devgn: When Bollywood brought real-life gangsters to the big screen

TOI Entertainment Desk
| ETimes.in | Last updated on - Dec 12, 2025, 12:00 IST
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1/9

Akshaye Khanna as Rehman Dakait in ‘Dhurandhar’

Akshaye Khanna recently appeared as the feared Rehman Dakait in the newly released ‘Dhurandhar’. His portrayal combined quiet menace with sharp unpredictability, making the character stand out in the large ensemble. The film showcased Khanna in a fierce, rugged avatar that audiences instantly connected with. His performance added significant weight to the narrative, earning praise for its intensity and precision.

2/9

Emraan Hashmi as Dawood Ibrahim in ‘Once Upon a Time in Mumbaai’

Emraan Hashmi stepped into the shoes of Dawood Ibrahim in ‘Once Upon a Time in Mumbaai’, a film that revisited Mumbai’s crime landscape of the 1970s. His portrayal captured the controlled aggression and rising ambition associated with the underworld don. Hashmi’s attention to detail made the character believable and layered. The film became a major success and added a defining performance to his career.

3/9

Ajay Devgn as Haji Mastan in ‘Once Upon a Time in Mumbaai’

Ajay Devgn played the iconic smuggler Haji Mastan through the fictionalised character Sultan Mirza in ‘Once Upon a Time in Mumbaai’. The film showcased Mirza’s rise to power and eventual decline within the underworld empire. Devgn’s calm authority and intensity gave the role immense weight. His performance remains one of the most talked-about depictions of the Mumbai mafia.

4/9

Seema Biswas as Phoolan Devi in ‘Bandit Queen’

Seema Biswas delivered a haunting performance as Phoolan Devi in ‘Bandit Queen’, one of Indian cinema’s most debated films. The movie chronicled the turbulent, traumatic and defiant life of the feared bandit. Biswas brought raw vulnerability and towering strength to the role, making the character unforgettable. Her performance earned widespread acclaim, eventually winning her the National Award in 1996.

5/9

Arjun Rampal as Arun Gawli in ‘Daddy’

Arjun Rampal portrayed gangster-turned-politician Arun Gawli in the political crime drama ‘Daddy’. The film explored Gawli’s tumultuous life, tracing his journey from the alleys of Mumbai to the world of politics. Rampal’s transformation for the role was widely praised for its authenticity. His performance brought a gritty, grounded tone to the biographical narrative.

6/9

Rishi Kapoor as Dawood Ibrahim in ‘D-Day’

Rishi Kapoor shocked audiences with his chilling performance as Dawood Ibrahim in ‘D-Day’. It was one of the rare times he played a full-fledged negative character on screen. Kapoor showcased the don’s ruthlessness with remarkable subtlety and control. His portrayal added unexpected depth to the veteran actor’s late-career filmography.

7/9

John Abraham as Manya Surve in ‘Shootout at Wadala’

John Abraham took on the role of the notorious gangster Manya Surve in ‘Shootout at Wadala’. The film revisited the sensational 1982 police encounter that ended Surve’s reign. Abraham’s physicality and emotional intensity added power to the character. The movie, loosely inspired by Hussain Zaidi’s ‘Dongri to Dubai’, became one of his most memorable performances.

8/9

Shraddha Kapoor as Haseena Parkar in ‘Haseena’

Shraddha Kapoor stepped into the role of Dawood Ibrahim’s sister in the biographical drama ‘Haseena’. The film traced Haseena Parkar’s evolution from a reserved young woman to a powerful figure within Mumbai’s crime network. Kapoor took on a drastic transformation to portray the character’s emotional and physical journey. The film also marked her brother Siddhanth Kapoor’s debut in Bollywood.

9/9

Vivek Oberoi as Chhota Rajan in ‘Company’

Vivek Oberoi gained widespread acclaim for his role inspired by Chhota Rajan in Ram Gopal Varma’s ‘Company’. The film explored the infamous fallout between Rajan and Dawood Ibrahim in gripping detail. Oberoi delivered a breakout performance marked by raw aggression and vulnerability. The movie remains a landmark in the gangster genre and a highlight of his career.

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Copyright © Jun 6, 2026, 08.17PM IST Bennett, Coleman & Co. Ltd. All rights reserved. For reprint rights: Times Syndication Service