Khan starred in seven films in 1995, the first of which was Rakesh Roshan‘s melodramatic thriller Karan Arjun. Co-starring Salman Khan and Kajol, it became the second-highest-grossing film of the year in India.^[65] His most significant release that year was Aditya Chopra‘s directorial debut, the romance Dilwale Dulhania Le Jayenge, in which he played a young Non-resident Indian (NRI) who falls in love with Kajol’s character during a trip across Europe. Khan was initially reticent to portray the role of a lover, but this film is credited with establishing him as a “romantic hero”.^[66] Lauded by both critics and the public, it became the year’s highest grossing production in India and abroad and was declared an “all time blockbuster” by Box Office India,^[65][67] with an estimated lifetime gross of ₹2 billion (US$61.68 million) worldwide.^[68][69] It is the longest-running film in the history of Indian cinema; it is still showing at the Maratha Mandir theatre in Mumbai after more than 1000 weeks as of early 2015.^[70][71] The film won ten Filmfare Awards, including the second of Khan’s Best Actor Awards.^[58] The director and critic Raja Sen said, “Khan gives a fabulous performance, redefining the lover for the 1990s with great panache. He’s cool and flippant, but sincere enough to appeal to the [audience]. The performance itself is, like the best in the business, played well enough to come across as effortless, as non-acting.”^[72]

In 1996, all four of Khan’s releases failed critically and commercially,^[73] but the following year, his starring role opposite Aditya Pancholi and Juhi Chawla in Aziz Mirza’s romantic comedy Yes Boss earned him accolades that included a Filmfare Best Actor nomination.^[61] Later in 1997, he starred in Subhash Ghai‘s diasporic-themed social drama Pardes,^[74] portraying Arjun, a musician facing a moral dilemma. India Today cites it as one of the first major Bollywood pictures to succeed in the United States.^[75] Khan’s final release of 1997 was the second collaboration with Yash Chopra in the popular musical romance Dil To Pagal Hai. 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.^[58]

Khan performed the lead role in three films and made one special appearance in 1998. In his first release of the year, he played a double role opposite Juhi Chawla and Sonali Bendre in Mahesh Bhatt’s action comedy Duplicate, the first of his many collaborations with Yash Johar‘s production company Dharma Productions. The film was not well received,^[76] but India Today lauded Khan for his energetic performance.^[77] The same year, Khan won critical praise for his performance as an All India Radio correspondent who develops an infatuation for a mysterious terrorist (Manisha Koirala) in Dil Se..,^[78] the third instalment of Mani Ratnam‘s trilogy of terror films.^[79][80] In his final release of the year, he portrayed a college student in Karan Johar‘s romance Kuch Kuch Hota Hai, in which he was involved in a love triangle along with Kajol and Rani Mukerji. The writer Anjana Motihar Chandra has referred to the picture as the blockbuster of the 1990s, a “pot-pourri of romance, comedy, and entertainment.”^[81] Khan won the Best Actor award at the Filmfare Awards ceremony for the second consecutive year,^[58] although he and several critics believed his performance to have been overshadowed by that of Kajol.^[82]

The roles in this phase of his career, and the series of romantic comedies and family dramas that followed, earned Khan widespread adulation from audiences, particularly teenagers,^[83] and according to the author Anupama Chopra, established him as an icon of romance in India.^[84][85] He continued to have frequent professional associations with Yash Chopra, Aditya Chopra, and Karan Johar, who moulded his image and made him into a superstar.^[86] Khan became a romantic leading man without ever actually kissing any of his co-stars,^[84] although he broke this rule in 2012, after strong urging by Yash Chopra.^[87]