Years before it was titled O Romeo, the film was originally conceived with the late Irrfan Khan cast as Ustra and Deepika Padukone set to play Sapna Didi. Both actors were signed on in 2017, with casting director Honey Trehan attached as the director. However, a series of delays over the years led to major changes in both the film’s team and its title. The project was initially slated to go on floors in January 2018, with a planned theatrical release on October 2 the same year. This schedule, however, was derailed due to delays in the filming of Deepika Padukone’s previous project, Sanjay Leela Bhansali’s Padmaavat.
According to a report in The Indian Express, the period drama faced intense opposition from the Shri Rajput Karni Sena, resulting in repeated disruptions, including one of the film’s sets being set on fire. Another major hurdle emerged in the form of creative differences between Honey Trehan and his mentor, Vishal Bhardwaj. Bhardwaj, who had introduced Trehan as a casting director and associate director with Makdee, eventually took over the project after his subsequent films failed to take off following the underperformance of his 2017 ambitious outing Rangoon, starring Shahid Kapoor, Saif Ali Khan and Kangana Ranaut.
Following his fallout with Bhardwaj, Trehan opted out of the film altogether. He later went on to make his directorial debut with the Netflix India whodunit Raat Akeli Hai in 2020, marking a new chapter in his career.
The third major setback came when Irrfan was diagnosed with a rare neuroendocrine tumour, forcing him to halt work and seek treatment in London, where he stayed for nearly two years before returning to India in 2020. He passed away shortly after in April 2020, while the project was further hit by production hurdles including the arrest of producer Prernaa Arora of KriArj Entertainment and the Covid-19 lockdown.
A couple of years ago, Vishal Bhardwaj finally revived the project after Sajid Nadiadwala came on board as producer, but with Irrfan no longer alive and Deepika unavailable due to other commitments and her pregnancy, the lead roles were recast with Shahid Kapoor and Triptii Dimri. The film also faced a last-minute hiccup when Randeep Hooda exited his role as Dawood days before the shoot and was replaced by Nana Patekar, while Avinash Tiwary, Disha Patani and Farida Jalal joined the ensemble. Originally titled Rani during the Irrfan–Deepika phase, the film underwent character and title changes after Shahid’s casting to avoid legal issues with Ustra’s family, leading to its final title O Romeo, which is now slated for a February 13 theatrical release amid fresh legal trouble.