Sohail’s debut film Auzaar did not do well at the box office. However his breakthrough came with his very next film, Pyaar Kiya To Darna Kya (1998) starring his brothers Salman Khan and Arbaaz Khan, a box office hit following then a lesser successful Hello Brother (1999). From Auzaar to Pyar Kiya To Darna Kya was definitely a box-office jump.

 In 2002 he wrote, produced, directed and made his acting debut in Maine Dil Tujhko Diya. The film did not do well at the box office and Sohail failed to launch his career as an actor. After his debut, Sohail then appeared in a few more films, none of them doing well at the box office. His first hit, as an actor was Maine Pyaar Kyun Kiya (2005) co-starring brother, Salman Khan and Kaitrina Kaif. Later he also wrote the story, produced and starred in the multi-starrer Fight Club - Members Only in 2006, which also did not do well at the box office. The same year he starred in the boxing drama Aryan co-starring a newcomer Sneha Ullal for which his performance was appreciated but the film failed at the box office due to delayed release.

 Later in 2007 he was starred in a multi-starrer Salaam-e-Ishq: A Tribute To Love and later produced Partner which starred his brother Salman Khan and Govinda in the lead roles, which was a huge box office success. He has also announced to star for the first time with both his brothers Salman and Arbaaz in Amar Akbar Anthony a remake of the 1977, Manmohan Desai film of the same name.