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Dilip Kumar in Swades, Dev Anand in Lootera, Shashi Kapoor in Jab We Met: AI recreation of modern 'classics' wins hearts

AI artist reimagined modern films featuring retro heroes like Dilip Kumar, Rishi Kapoor, Dev Anand, Dharmendra, Shammi Kapoor, Shashi Kapoor, and Rajesh Khanna.

Updated on: Apr 05, 2026 02:35 PM IST
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Ever imagined how icons like Dilip Kumar, Shammi Kapoor, or Dev Anand would look if they were cast in Bollywood films from the 21st century? Thanks to AI, that vision is now a reality. An AI artist known as AI Tot on Instagram shared a stunning compilation of looks reimagining swaps of iconic Bollywood superstars for moder Hindi films. The new video featured a lineup of legendary Indian actors, reimagined in contemporary Bollywood films, including Swades, Jab We Met, Lootera, and My Name Is Khan. (Also read: AI imagines Dhurandhar in Mollywood: Fahadh Faasil as Rehman Dakait, Nazriya Nazim as Yalina, Unni Mukundan as Hamza)

Dev Anand in Lootera to Shashi Kapoor in Jab We Met

Iconic Bollywood actors like Dev Anand, Shashi Kapoor, and Dilip Kumar were cast in modern films in an AI-generated video. (Instagram/@aitot.2.0)
Iconic Bollywood actors like Dev Anand, Shashi Kapoor, and Dilip Kumar were cast in modern films in an AI-generated video. (Instagram/@aitot.2.0)

In the post, a young Dev Anand was cast in Lootera, where he is seen as Varun (played by Ranveer Singh). The clip shared showed Dev with a brooding intensity mixed with doubt that perfectly mirrors his character in the film. Actor Suraiya- who had a real connection with Dev during her days in the film industry- was seen in the role of Pakhi (played by Sonakshi Sinha).

Rajesh Khanna was seen with his arms stretched wide, just like Shah Rukh Khan, as he was imagined in the film Kal Ho Naa Ho. Shashi Kapoor was seen as Rohit (played by Saif Ali Khan). Suresh Oberoi looked suave and handsome as Aditya in Saathiya, a role that his son Vivek Oberoi made so memorable on screen. Sanjeev Kumar starred as Rizwan from My Name is Khan (a role played by Shah Rukh Khan).

In a casting coup, the 'what if' scenario imagined how Zindagi Na Milegi Dobaara would look like if it were made with Dharmendra, Rakesh Roshan and Javed Akhtar. Abhay Deol (Dharmendra's son), Hrithik Roshan, and Farhan Akhtar (Rakesh and Javed's sons) acted in the film. Stepping in for Aamir Khan as Rancho in 3 Idiots was Shammi Kapoor, who brought the same awkward energy to the part. Meanwhile, Rishi Kapoor and Amrita Singh replaced Aamir Khan and Preity Zinta in Dil Chahta Hai.

However, it was Shashi Kapoor's look as Aditya in Jab We Met that caught the attention of most social media users. Shashi looked handsome and suited the guardedness required for the role, which was played by Shahid Kapoor in the film. Reacting to it, a fan commented, “Shashi ji's look left me stunned. Wow, he looks so handsome!” Another said, “Dev Anand and Shashi Kapoor look best. How cool it would be!”

Note to readers: This report is based on user-generated content from social media.

 
ABOUT THE AUTHOR
Santanu Das

Santanu Das is a Senior Content Producer at Hindustan Times with over 5 years of experience, writing on films, pop culture and film festivals. He has a keen interest in writing about South Asian independent films and has covered several film festivals, including Sundance and CPH: Docx. He also brings a sharp perspective to the monthly column called The Fault in Our Stars, where he writes about a recent film/series and what stops the ‘good’ from becoming ‘great’. A gold medalist from Banaras Hindu University, Santanu completed his postgraduate studies in English from Jadavpur University. He is also a Rotten Tomatoes-certified film critic. When not watching films or speaking to celebrities, Santanu can be found reading a book. Some of his favourite films are Aparajito, Ponyo and The Double Life of Veronique. His favourite books include The Corrections, The God of Small Things and A Room of One's Own. Santanu continues to write passionately about films and celebrity culture. He brings a relatable, as well as critically informed, lens to entertainment and culture for a wide audience. Find him on LinkedIn: santanudasfilm Instagram: @santupecha

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