|Appeared as a child actor in the movie Dharam Veer in 1977. Deol then made his adult debut with Twinkle Khanna in the Bollywood film Barsaat in 1995, directed by Rajkumar Santoshi. Deol plays the character of Badal, a naïve but intelligent young man who moves from a small village to the big city and finds himself caught by corrupt police and criminal gangs falling in love.
Partly shot in Scotland, Deol broke his leg during an equestrian accident during a film shoot and had to be repatriated to London to recover and had to cancel several publicity sessions that documented his debut.The film was nevertheless a considerable success and earned him the Filmfare Best Debut Award .
In 1997, Deol played in Gupt: The Hidden Truth, a thriller thriller directed by Rajiv Rai, considered his breakthrough role. Alongside Manisha Koirala, Kajol, Paresh Rawal, Om Puri and Raj Babbar, Deol played the role of Sahil, a young man accused of murdering his father-in-law on a commitment proposal. and unjustly imprisoned. He escapes and tracks down the real killer. Gupt: The Hidden Truth was very acclaimed for its story and soundtrack and was a major commercial success. In the same year, Deol appeared at Aur Pyaar Ho Gaya, alongside Aishwarya Rai in his first Bollywood role. The film did not work well at the box office.
In 1998, Deol played in front of Neha in the movie Vidhu Vinod Chopra, Kareeb. Deol played the character of Birju, an irresponsible young man from a middle class family in Himachal Pradesh, with a love of petty theft and deception.
Later in 1998, he appeared in the military thriller Soldier by Abbas Mustan, alongside Raakhee and Preity Zinta. Deol played the mysterious character of Vicky, later revealed as Raju, son of Vijay Malhotra who was convicted of smuggling weapons.
In 1999, Deol played in Dillagi, directed and co-starred with his brother Sunny Deol. The film is noted for being the first time that Sunny Deol made a film and also the first time he acted alongside Bobby. This association was repeated on March 23, 1931: Shaheed , Apne and Yamla Pagla Deewana . Dillagi presents the two as brothers Ranvir and Rajvir, fighting for the affection of Shalini.
In 2000, Deol appeared in the Badal action drama alongside Rani Mukerji, under the direction of Raj Kanwar.