R Madhavan had a cameo-like appearance in the cult classic Rang De Basanti (2006). As director Rakeysh Omprakash Mehra writes, "This was the shortest and most challenging role around which the whole film revolved." The film is about a group of good-for-nothing guys who decide to stand up for their country after their friend Flt Lt Ajay Rathod (R Madhavan) dies in an air crash. Today, it’s difficult to imagine anyone else in the said role. However, Rakeysh Omprakash Mehra in his autobiography ‘The Stranger In The Mirror’, co-authored by Reeta Ramamurthy Gupta, revealed that R Madhavan was not the first choice. Shah Rukh Khan was offered the role when he was shooting for Swades (2004). But since he didn’t have dates, he declined.
Rakeysh's autobiography also has the first-person account of R Madhavan. The actor writes that he was blown away by Rang De Basanti's script, especially because it was very detailed. Interestingly, R Madhavan was also offered the role of Karan Singhania, which was ultimately played by Siddharth. R Madhavan then was shooting for Thambi (2006) then and had shoulder-length hair. Since the role of Ajay Rathod required just 8 days, he took up the role.
However, the shoulder-length role was still a problem and wouldn't have gone with his pilot character in Rang De Basanti. R Madhavan revealed that the makers organized a special wig for him, costing Rs. 70,000. Seeing the effort they are putting in to retain him, Madhavan writes that he couldn't refuse.
The first scene that R Madhavan shot was when he proposes to Soha Ali Khan. A shot required her to kiss her. At this, R Madhavan raised laughs as he wrote, "The only thing I could think of was Saif (Soha's brother, with whom I had worked before in a tense movie as rivals) socking my face. But I had to establish that I was an ideal boyfriend. This was probably her first on-screen kiss as well." The tense film mentioned by R Madhavan was Rehnaa Hai Terre Dil Mein (2001).
The kiss was important but Madhavan stated that Rakeysh Omprakash Mehra could sense the discomfort that the actors were facing. Hence, the filmmaker decided to keep the shot in a silhouette.
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