Jagdeep started his career as a comedian with Bimal Roy's Do Bigha Zameen which was followed by Teen Bahuraniyan (1968), Jeene Ki Raah (1969) ,Darpan (1970), Gora Aur Kala (1972), Aankh Micholi (1972), Insaaniyat (1974), Jaggu (1975), Chala Murari Hero Banne (1977) and many more. He even played the role of hero in five films, including Bhabhi with Nanda and another film Barkha.
Do Bigha Zameen was followed by Guru Dutt's maiden production, Aar Paar (1954). He then acted in Aasman, Bhaisahab, Dhake Ki Malmal and Dhobi Doctor, which was Bimal Roy's first production. In the film Shikwa, he played the role of young Dilip Kumar. In the films Ek Masoom and Mandir-Masjid, his roles had a negative shade..
Jagdeep's most acclaimed comic role is the character Soorma Bhopali in Sholay. The film is considered to be one of the greatest movies of Bollywood. He has worked in more than 400 Hindi films. He directed a film titled Soorma Bhopali, which was a pure entertainer.