And that, dear reader, is the real once-upon-a-time.
When Once Upon a Time in Mumbaai hit the screen in 2010, it wasn’t just another Bollywood gangster film. It was a slow-burn, morally grey love letter to an era—the 1970s Bombay of polyester shirts, rotary phones, and rising crime. But the film’s real magic lay in its casting. Director Milan Luthria assembled a trio of actors who didn’t just play their parts; they inhabited the ghosts of Mumbai’s underworld.
Art imitated life. A few years later, Kangana would become Bollywood’s most fearless rebel, fighting the very "gangsterism" of film politics. Watching Once Upon a Time in Mumbaai today, you realize she wasn’t acting—she was rehearsing for her own war. The Secret Ingredient: Randeep Hooda (The Forgotten Genius) No article on this film is complete without Randeep Hooda, who played the honest cop, Agnel Wilson. In a film of grey characters, Hooda brought a tragic black-and-white hero. His screen time is just 12 minutes, but his final confrontation with Devgn— "Main tumse chhoti gundi nahi, bade aadmi ki tarah baat kar raha hoon" (I’m not a small crook talking to you, I’m a big man)—is the film’s moral compass. Hooda spent a week living in a real Mumbai police chowky to learn the casual swagger of a 70s officer. Conclusion: Why It Still Works Once Upon a Time in Mumbaai works not because of its shootouts or its retro soundtrack, but because of a perfect storm of casting: the stoic veteran (Devgn), the hungry outsider (Hashmi), the rebellious woman (Ranaut), and the honest mirror (Hooda). They weren’t just playing gangsters. They were playing versions of themselves, dressed in bell-bottoms and betrayal. once upon a time in mumbai actors
Kangana was just 23 when she shot the film. Her character is torn between the dignified Sultan (Devgn) and the dangerous Shoaib (Hashmi). Originally, her role was just eye-candy—a few songs and a weepy scene. Kangana famously fought with Luthria, demanding that Rehana have a spine. She improvised the climactic monologue where she slaps Shoaib and says, "Tum logon ki dosti mein dum hi nahi" (Your friendship has no strength).
Let’s pull back the velvet curtain on the three leads: Ajay Devgn, Emraan Hashmi, and Kangana Ranaut. Their real stories, struggles, and techniques are as dramatic as the film itself. Ajay Devgn played Sultan Mirza—a fictionalized version of the real-life don Haji Mastan. Sultan is a man who wants to be a kingpin with a conscience: he smuggles gold but builds hospitals, wears white khadi, and quotes Urdu poetry. And that, dear reader, is the real once-upon-a-time
Devgn insisted that his character’s signature white kurta-pyjama be starched so stiffly that it crinkled audibly. He believed that the sound of power was the rustle of crisp cotton, not the click of a gun. 2. Emraan Hashmi: The Serpent and the Scene-Stealer If Devgn is the iceberg, Emraan Hashmi’s Shoaib Khan (based on Dawood Ibrahim) is a wildfire. Shoaib starts as a loyal protégé and morphs into a hungry, slick-haired beast who wants to own Bombay.
Hashmi studied clips of Robert De Niro in The Untouchables and real footage of Dawood Ibrahim. He added a unique tic: Shoaib constantly smooths his hair back, as if physically pushing away any sentimentality. The result? By the climax, you forget you’re watching the guy from Murder —you’re just terrified of Shoaib. 3. Kangana Ranaut: The Wildcard Who Rewrote the Script As Rehana, the star-struck village girl who becomes a conflicted moll, Kangana Ranaut delivered a masterclass in vulnerability. But the interesting part happened off-screen. But the film’s real magic lay in its casting
This was the film that broke Emraan Hashmi out of his "serial kisser" cage. Luthria took a massive risk casting him. At the time, critics saw Hashmi as a B-grade romantic hero. But Hashmi has admitted in interviews that he channeled a deep, personal rage into the role. He was tired of being underestimated. That raw hunger you see in Shoaib’s eyes? That’s not acting—that’s an actor fighting for legitimacy.