In 1991, Khan was cast as the male lead in Rahul Rawail's romantic drama Bekhudi (1992) alongside debutante Kajol, but after completing the first shooting schedule of the film, he was considered to be unprofessional by Rawail and was replaced by Kamal Sadanah.
hile filming Bekhudi, Khan met actress Amrita Singh whom he married in October 1991. Singh gave birth to their daughter (Sara Ali Khan) and son (Ibrahim) in 1995 and 2001 respectively, and the couple later separated in 2004. In 1993, Khan made his acting debut with Parampara, a drama directed by Yash Chopra. The film, which tells the story of two estranged brothers (played by Aamir Khan and Khan), failed to find a wide audience. He next appeared opposite Mamta Kulkarni and Shilpa Shirodkar in the box office flops Aashiq Awara and Pehchaan (both 1993) respectively, but Khan earned the Filmfare Award for Best Male Debut for his performance in Aashiq Awara at the 39th Filmfare Awards.
Following an appearance in the moderately successful drama Imtihaan (1994), Khan starred in and earned public recognition with his next two releases opposite Akshay Kumar: Yash Raj Films' hit romantic drama Yeh Dillagi and the action film Main Khiladi Tu Anari