The 2005 film "Parineeta," a cinematic adaptation of Sarat Chandra Chattopadhyay's Bengali novella, marked Vidya Balan's Bollywood debut and featured Saif Ali Khan and Sanjay Dutt in leading roles. However, the initial casting process involved a different set of actors, and a surprising rejection from a "star kid" paved the way for Saif Ali Khan to become the iconic Shekhar Rai.

According to reports, Abhishek Bachchan was initially considered for the role of Shekhar, while Saif Ali Khan was slated to play Girish. However, Abhishek Bachchan exited the project, leading to Saif Ali Khan's acceptance as Shekhar Rai.

Saif Ali Khan himself acknowledged that director Pradeep Sarkar wasn't initially convinced about his suitability for the role. The actor, known for his roles in romantic comedies like "Hum Tum" and "Salaam Namaste", found Shekhar Rai to be a departure from his established image. "At that time, I was used to the typical romantic hero parts," Saif Ali Khan stated, adding, "But Shekhar was complicated. He was proud, vulnerable, and not always easy to like".

The role presented him with an opportunity to explore a more layered character, one with both positive and negative shades. Shekhar's journey in "Parineeta" involves growth and self-discovery, aspects that resonated with Saif Ali Khan and allowed him to push his boundaries as an actor. He aimed to bring a sense of elegance to the classic role.

While the identity of the "star kid" who allegedly turned down the role of Vidya Balan's "lover" remains unconfirmed in available sources, it's clear that the casting choices for "Parineeta" underwent significant changes before the film's release. It is also not clear which role was turned down.

Vidya Balan's casting as Lalita was also not without its initial hurdles. Vidhu Vinod Chopra, the film's producer, had screen-tested Vidya Balan for six months to be sure of her acting abilities. Saif Ali Khan confessed he had hoped to work with established actresses and was not initially convinced of Vidya's abilities, given that "Parineeta" was to be her first film. However, after witnessing her portrayal of Lalita, he was thoroughly impressed and appreciative of her performance.

"Parineeta" tells the story of childhood friends Lalita and Shekhar, whose relationship is tested by misunderstandings and the schemes of Shekhar's father. The arrival of Girish, who supports Lalita's family, further complicates matters. Ultimately, Shekhar's love for Lalita triumphs over his father's greed.

Upon its release on June 10, 2005, "Parineeta" became a commercial success and garnered positive reviews. Critics praised the film's screenplay, soundtrack, production design, costumes, and the performances of the cast, particularly Vidya Balan's debut. Saif Ali Khan received a Filmfare nomination for Best Actor for his portrayal of Shekhar Rai. Looking back on the film, Saif Ali Khan expressed pride in his work and acknowledged that "Parineeta" remains one of his favorite films. He also lauded Vidya Balan for bringing "poetry to the role" and praised the film's recreation of 1960s Kolkata.