Among his 1993 releases, Khan garnered the most appreciation for portraying villainous roles in two box office hits: a murderer in Baazigar, and an obsessive lover in Darr.^[55] The former, in which Khan played an ambiguous avenger who murders his girlfriend, shocked Indian audiences with an unexpected violation of the standard Bollywood formula.^[56] In The Cambridge Companion to Modern Indian Culture, Sonal Khullar called the character “the consummate anti-hero”.^[57] His performance in Baazigar, which would be his first of many appearances with actress Kajol, won Khan his first Filmfare Award for Best Actor.^[58] In 2003, the Encyclopaedia of Hindi Cinema stated that Khan “defied the image of the conventional hero in both these films and created his own version of the revisionist hero”.^[58] Darr marked the first of Khan’s many collaborations with filmmaker Yash Chopra and his company Yash Raj Films. Khan’s stammering and the use of the phrase “I love you, K-k-k-Kiran” were popular with audiences.^[59] Malini Mannath of The Indian Express argued that he “walks away with the acting honours in yet another negative role”.^[60] For Darr he received a nomination for the Filmfare Award for Best Performance in a Negative Role, also known as the Best Villain Award, but lost to Paresh Rawal for Sir.^[61] Also in 1993, Khan performed a nude scene with Deepa Sahi in Maya Memsaab, although parts of it were censored by the Central Board of Film Certification.^[62] The ensuing controversy prompted him to eschew such scenes in future roles.^[63]

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 Rediff.com referred to it as Khan’s best performance, calling him “spontaneous, vulnerable, boyish, mischievous and acting straight from the heart”.^[64] Also in 1994, Khan won the Filmfare Best Villain Award for his role as an obsessive lover in Anjaam, co-starring Madhuri Dixit.^[58] At the time, playing antagonistic roles was considered risky to a leading man’s career in mainstream Hindi cinema. Arnab Ray subsequently credited Khan for taking “insane risks” and “pushing the envelope” by choosing to play such characters, through which he established his career.^[54] The director Mukul S. Anand called him “the new face of the industry” at the time.^[48]