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All nine films in which he starred—Surakshaa (1995), Ek Tha Raja (1996), Bambai Ka Babu (1996), Tu Chor Main Sipahi (1996), Dil Tera Diwana (1996), Hamesha (1997), Udaan (1997), Keemat: They Are Back (1998) and Humse Badhkar Kaun (1998)—were critically and commercially unsuccessful.
After four consecutive years of poorly received films, Khan's career prospects began to improve in 1999; he appeared in four films: Yeh Hai Mumbai Meri Jaan, Kachche Dhaage, Aarzoo and Hum Saath-Saath Hain.
He earned wide critical praise for his portrayal of a manipulative businessman in the 2004 thriller Ek Hasina Thi, an apprentice in the 2006 English film Being Cyrus, a character based on William Shakespeare's antagonist Iago in the 2006 crime film Omkara, and a terrorist in the 2009 thriller Kurbaan.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.1, an adaptation of David Dhawan's 1995 film of the same name. The son of actress Sharmila Tagore and cricketer Mansoor Ali Khan Pataudi, Khan made his acting debut in Yash Chopra's unsuccessful drama Parampara (1993), but achieved success with his roles in the romantic drama Yeh Dillagi and the action film Main Khiladi Tu Anari (both 1994).