[[Aamir Khan]] had initially been offered the role of Narendra;, but he declined.<ref name=":1">{{Cite web |last=शुक्ल |first=पंकज |date=15 April 2021 |title=Bioscope S2: शाहरुख के लिए सोचा गया था '1942 ए लव स्टोरी' में ये वाला रोल, ऐसे हुई मनीषा की एंट्री |trans-title=Bioscope S2: This role in '1942 A Love Story' was thought for Shah Rukh; Manisha's entry happened in this way |url=https://www.amarujala.com/photo-gallery/entertainment/bollywood/bioscope-by-pankaj-shukla-1942-a-love-story-jackie-shroff-anil-kapoor-manisha-vidhu-chopra-rd-burman |url-status=live |archive-url=https://web.archive.org/web/20210416044909/https://www.amarujala.com/amp/photo-gallery/entertainment/bollywood/bioscope-by-pankaj-shukla-1942-a-love-story-jackie-shroff-anil-kapoor-manisha-vidhu-chopra-rd-burman |archive-date=16 April 2021 |access-date=6 June 2022 |website=[[Amar Ujala]] |language=hi}}</ref> [[Anil Kapoor]] was then approached, who was hesitant to do the film and suggested [[Bobby Deol]] and Aamir Khan for the role. However, he was later convinced. To prepare himself for the role, Kapoor worked hard — he lost weight, cut short his hair, trimmed his moustache and worked on his costumes to create the character.<ref>{{Cite web |last=Bhasin |first=Shriya |date=4 November 2019 |title=Anil Kapoor reveals why he initially refused '1942: A Love Story' |url=https://www.indiatvnews.com/entertainment/celebrities/anil-kapoor-reveals-why-he-initially-refused-1942-a-love-story-561279 |url-status=live |archive-url=https://web.archive.org/web/20191105204425/https://www.indiatvnews.com/entertainment/celebrities/anil-kapoor-reveals-why-he-initially-refused-1942-a-love-story-561279 |archive-date=5 November 2019 |access-date=7 June 2022 |website=[[India TV]] |language=en}}</ref> [[Shah Rukh Khan]] was under consideration for the role later done by [[Raghuvir Yadav]]; he did not feature as he had already been playing lead roles.<ref name=":1" /> [[Jackie Shroff]] was cast as Shubankar. He gave financial assistance to the film. For instance, some (extra) houses built at the film's set (which were first disapproved of by Vidhu Vinod Chopra due to the limited budget) were paid for by Shroff. Moreover, he also paid composer [[R. D. Burman]] on behalf of Chopra when he made them listen the music of the film for the very first time.<ref name=":0" />
