Shroff dropped out of school after his 11th standard as his family did not have much money. He tried his hand working as an apprentice chef at Taj Hotels and as a flight attendant at Air India, but he was rejected from both places because of his lack of qualifications. He then started working as a travel agent in a local company called “Trade Wings” near Jehangir Art Gallery. An advertising agency accountant spotted him at the bus stand and asked him if he would be interested in modelling. The next day, Shroff went to the advertising agency (National advertising agency) located in the same building as Davar’s college near Flora Fountain for the photo shoot during his lunch time. This photo shoot for a suit shirt launched Shroff on his modelling path. In 1982, Shroff made his acting debut in Dev Anand’s movie Swami Dada. In 1983, Subhash Ghai cast him in the lead role for the movie Hero, paired against Meenakshi Seshadri. The film was a success. He continued to work in Subhash Ghai movies, irrespective of any role that was offered. After Hero, he did several other films, such as Andar Baahar. Jaanoo and Yudh were successful. In 1986 he did Karma which became the highest-grossing film of 1986. His next film to be released was Kaash. Later films, such as Dahleez and Sachché Ká Bol-Bálá were critically acclaimed, but failed at the box office. But he came back to success through films such as Ram Lakhan, Tridev, and Parinda, which won him filmfare award for best actor. In the 90s he was part of successful films such as Saudagar, Angaar, Sapne Sajan Ke, Gardish, Khalnayak, 1942: A Love Story, Rangeela, Agnisakshi, Border, And Shapath.

In 2006, Shroff acted in the children’s film Bhoot Unkle.

Shroff has hosted many television shows like Lehrein, Chirtrahar and Missing. Dealing with stories of missing people who were never found, Missing was popular for its creative narration by Shroff. The show was broadcast on Sony TV, of which he owned some shares. Shroff was also a judge on the magic show India’s Magic Star, broadcast on Indian channel STAR One. The show began on 3 July 2010 and ended on 5 September 2010. In 2014, Shroff and his son Tiger Shroff made an appearance on Comedy Nights with Kapil. In 2019 Shroff made his digital debut with the series Criminal Justice.

In 2017, Shroff made his debut in Konkani, acting in the film Soul Curry, which even won him an award. Subsequently, he is to act in another Konkani film scheduled to release in 2019, titled Kantaar.

In October 2018, he acted in a short film, The Playboy Mr. Sawhney. He was also seen in Paltan. He is to feature in many films in 2019, like Firrkie, Bharat, Saaho, and Romeo Akbar Walter. He is also going to star in Prasthanam, which Hindi remake of Telugu film with same name alongside Ali Fazal and Sanjay Dutt.