Khan, who made his acting debut with the film Biwi Ho To Aisi (1988), had his first commercial success with the blockbuster Maine Pyar Kiya (1989), and won a Filmfare Best Male Debut Award for his performance. He went on to star in some of Bollywood's most successful films, such as Saajan (1991), Hum Aapke Hain Kaun (1994), Karan Arjun (1995), Judwaa (1997), Biwi No.1 (1999), having appeared in the highest earning films of six separate years during his career.

In 1999, Khan won a Filmfare Best Supporting Actor Award for his extended appearance in Kuch Kuch Hota Hai (1998), and since then has starred in several critical and commercial successes, including Hum Dil De Chuke Sanam (1999), Tere Naam (2003), No Entry (2005), Partner (2007), Wanted (2009) and Dabangg (2010), which has become the second highest-grossing Bollywood film of all time after 3 Idiots. Khan has thus established himself as one of the most prominent leading actors of Hindi cinema.

1990 saw only one film release starring Khan, Baaghi, alongside southern actress Nagma. The film was a box office success, and was followed by another successful year in 1991 when he starred in three hit films, Patthar Ke Phool, Sanam Bewafa and Saajan. Despite these early successes, all of his 1992-1993 releases resulted in box office failures.

Khan clawed back his previous success in 1994 with his second collaboration with director Sooraj Barjatya in the romance Hum Aapke Hain Kaun, co-starring Madhuri Dixit. This film was the biggest hit of that year, and turned out to be one of Bollywood's highest grossing films ever, becoming the fourth highest earner of all time. Apart from being a commercial success, the film was widely acclaimed and Khan was praised for his performance, earning his second nomination for Best Actor at the Filmfare. Three more films released that year featured Khan, none of which making a significant impact on the box-office as was the case with the previously mentioned title. He did however win praise for his performance in Andaz Apna Apna, alongside co-star Aamir Khan, which has gained a cult status since its release. In 1995 he cemented his success with Rakesh Roshan's blockbuster Karan Arjun, co-starring alongside Shahrukh Khan.The film was the second biggest hit of the year, and his role of Karan once again put his name among the nominees for the Best Actor award at the Filmfare, which was eventually won by his Karan Arjun co-star Shahrukh Khan.

1996 was followed by two successes. The first one being Sanjay Leela Bhansali's directional debut Khamoshi: The Musical, co-starring Manisha Koirala, Nana Patekar and Seema Biswas. Though a box office failure, the film was critically acclaimed. He next starred alongside Sunny Deol and Karisma Kapoor in Raj Kanwar's action hit Jeet.

He had only two releases in 1997: Judwaa and Auzaar. The former was a comedy directed by David Dhawan co-starring Karisma Kapoor, where he played a dual role of twins separated at birth. The film was a box office hit. The latter, co-starring Shilpa Shetty failed to do well, but developed a cult following after its video release.

Khan worked in five different films in 1998, his first release being the comedy Pyaar Kiya To Darna Kya opposite Kajol, one of the biggest commercial successes of that year. This was followed by the moderately successful drama Jab Pyaar Kisise Hota Hai. Khan played a young man who has to take a child who claims to be his son, under his custody. Khan's performance in the film earned him several positive notices and favourable reviews from critics. He rounded of the year with Karan Johar's directorial debut, Kuch Kuch Hota Hai. Co-starring alongside Shahrukh Khan and Kajol, he had only an extended cameo playing the role of Aman. However, it eventually turned out beneficial to him, as his performance earned him his second Filmfare Award under the Best Supporting Actor category.

In 1999, Khan starred in three hit films: Hum Saath-Saath Hain: We Stand United, which reunited him with Sooraj Barjatya for the third time; Biwi No.1, which became the top grossing film that year; and Hum Dil De Chuke Sanam, which was a major critical success, and earned him another Best Actor nomination at the Filmfare.