On a chat show with Simi Garewal, Jackie spoke about the lesser known facts of his life one of them being how he turned from Jaikishan Kakubhai to Jaggu Dada. He said, "My brother was the real Jaggu Dada of our chawl. He used to take care of our slum people, look after them when in need. But at a very young age, unfortunately my brother jumped into the sea to save someone. And my brother did not know swimming so he also started drowning. I threw a cable line at him, he held onto it, was floating for few seconds but the cable slipped out of his hands. I was young and scared and I stood there watching him drown. After him, I decided I had to look after my slum people just like he does and then I turned into Jaggu dada."
Jackie Shroff who always had an inclination for style and cooking, tried his luck at Taj as a chef apprentice. Jackie Shroff is a good cook and his 'baigan ka bhartha' is famous among Bollywood stars. But Taj rejected him as he fell short of the degrees they wanted.
After this, Jackie tried hi luck at Air India for the post of Flight Stuart, but there again he was rejected for falling short of the minimum qualifications. Then one fine day while he was waiting for his bus at a bus stop, a man walked upto him and asked 'modelling karega?'. Jackie who was not earning that time quickly asked, 'paisa dega kya' and from this moment his journey towards stardom began.