Khan began his career with appearances in several television series in the late 1980s. Early in his career, Khan was recognised for portraying villainous roles in the films Darr (1993), Baazigar (1993) and Anjaam (1994).
Khan's stammering and the use of the phrase "I love you, K-k-k-Kiran" were popular with audiences.
In 1994, Khan played a love-struck musician in Kundan Shah's comedy-drama film Kabhi Haan Kabhi Naa opposite Deepak Tijori and Suchitra Krishnamurthy, which he later professed was his favourite role.
His performance earned him a Filmfare Critics Award for Best Performance, and in a retrospective review from 2004, Sukanya Verma of referred to it as Khan's best performance, saying "He is spontaneous, vulnerable, boyish, mischievous and acting straight from the heart." At the time, playing antagonistic roles was considered risky to a leading man's career in Bollywood.
He portrayed Rahul, a stage director caught in a love triangle between Madhuri Dixit and Karisma Kapoor.
The film and his performance met with critical praise, winning Khan his third Best Actor Award at Filmfare.
Ray subsequently credited Khan for taking "insane risks" and "pushing the envelope" by choosing to play such characters, through which he established his career in Bollywood.