1970–1986

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After his father's (Roshan) untimely death, Rakesh started his career as an assistant director to film-maker Mohan Kumar in films like Anjaana starring Rajendra Kumar and Babita. Actor Rajendra Kumar referred him to some film-makers and thus he was signed by Soodesh Kumar for Man Mandir starring Sanjeev Kumar and Waheeda Rehman. But he made his entry as an actor, making his debut in the 1970 film Ghar Ghar Ki Kahani, in which he got a supporting role.^[3] He got very few solo hero films in his career. He got solo hero roles in more women-oriented films where the focus was more on the heroine, such as Paraya Dhan with Hema Malini, Aankh Micholi with Bharati, Khubsoorat with Rekha and Kaamchor with Jaya Prada. His few successful solo hero films, with the focus equally on both hero and heroine, were Aankhon Aankhon Mein with Rakhee, Nafrat with Yogita Bali, Ek Kunwari Ek Kunwara with Leena Chandavarkar, Hamari Bahu Alka with Bindiya Goswami and Shubh Kaamna with Rati Agnihotri. J. Om Prakash produced Aankhon Aankhon Mein with Rakesh in the lead. Later, J. Om Prakash directed Aakraman, with Sanjeev Kumar in the lead, and had Rakesh in a supporting role, and then produced Aakhir Kyun?, with Rajesh Khanna in the lead and Rakesh in a supporting role. Rakesh played supporting roles in a few successful films such as Man Mandir with Sanjeev Kumar in the lead, Khel Khel Mein with Rishi Kapoor in the lead, Bullet with Dev Anand as the hero, Hatyara with Vinod Khanna in the lead, Dhongee with Randhir Kapoor, Khandaan with Jeetendra and Neeyat with Shashi Kapoor as the lead hero. He played supporting roles regularly in films with Rajesh Khanna in the lead role and of those, Chalta Purza was a failure and the other three were blockbusters - Dhanwan, Awaaz and Aakhir Kyon?. The few multi-star cast films he was part of as the lead hero that were successful between 1977 and 1986 were Devata, Shriman Shrimati and Haathkadi, all of which had Sanjeev Kumar as the main lead hero and Jaag Utha Insan and Ek Aur Sikander, which had Mithun Chakraborty in the main lead, and other hits such as Dil Aur Deewaar, Khatta Meetha, Unees-Bees (1980) and Maqaar (1986). Most of his other films as a second lead hero or solo hero films between 1973 and 1990 were box office flops.

Rakesh set up his own production company, Filmkraft, in 1980 and their first production was Aap Ke Deewane (1980), which was a box office flop. His next venture was Kaamchor, also produced by him, which became a hit, but the success of this film was attributed to its music and the heroine Jaya Prada. His next solo hero film Shubh Kaamna, directed by K. Vishwanath, was a hit. He tried to re-launch himself as a lead hero with Bhagwaan Dada (1986), directed by J. Om Prakash and starring Rajinikanth as the main lead and himself in the second lead. But Bhagwaan Dada was a flop. Between 1984 and 1990 he only got supporting roles, with the exception of Bahurani. The multi-star films where he was the second lead, such as Maqaar and Ek Aur Sikander were successful. His last film as a leading hero was Bahurani, which was a woman-oriented film starring Rekha in the lead, which was directed by Manik Chatterjee and released in 1989.

1987–1999

He made his directorial debut with the action drama Khudgarz (1987), starring Jeetendra, Shatrughan Sinha, Govinda, Bhanupriya, Amrita Singh and Neelam Kothari. The film emerged as a Huge commercial success and an Huge Hit at the box-office. The film became a Blockbuster Success.

He next directed the revenge drama thriller Khoon Bhari Maang (1988), starring Rekha alongside Kabir Bedi and Sonu Walia. The film received highly positive reviews upon release, and became a major commercial success at the box-office. It was also noted as a path-breaking film, emerging as one of the first successful films with the heroine as the central protagonist. The film also earned Rekha her second Filmfare Award for Best Actress, in addition to Roshan's first nominations for Best Film and Best Director. He followed it up with the action comedy Kishen Kanhaiya (1990), starring Anil Kapoor in a double role, alongside Madhuri Dixit and Shilpa Shirodkar.

His next directorial venture was the melodramatic thriller Karan Arjun (1995), starring an ensemble cast of Raakhee Gulzar, Salman Khan, Shah Rukh Khan, Kajol, Mamta Kulkarni and Amrish Puri in lead roles. The film received positive reviews from critics, and emerged as a blockbuster at the box-office, ranking as the second-highest-grossing Indian film of the year. It also earned Roshan his second nominations for the Filmfare Award for Best Film and Best Director.

He next directed the action thriller Koyla (1997), starring Shah Rukh Khan and Dixit. The film received mixed reviews from critics, and emerged as an average grosser at the box-office, ranking as the ninth highest-grossing Indian film of the year.

2000–present