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Começando sua carreira trabalhando em vídeos de música e propagandas, Shahid fez sua estréia em Bollywood como dançarino de fundo no filme Taal do Subhash Ghai (1999). Quatro anos mais tarde, ele fez sua estréia como protagonista em Ishq Vishk (2003) e ganhou um prêmio Filmfare de estréia como melhor ator por seu desempenho. Aclamado por suas performances em filmes como Fida (2004) e Shikhar (2005), ele teve seu primeiro sucesso comercial com filme Vivah de Sooraj R. Barjatya (2006) em seguida com Jab We Met (2007) e Kaminey (2009), que também são seus maiores sucessos comerciais até agora.
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