Mani Ratnam's Bombay and Ram Gopal Varma's Sarkar were two such films. Both films were shown to the Shiv Sena supremo before they were released. 

In Bombay (1995), the character resembling Thackeray plays a key role in the communal riots that follows the demolition of the Babri Masjid. In a column titled, 'Sexism more than communalism' , Swaminathan S Anklesaria Aiyar had written then, "Mr Mani Ratnam showed the film in advance to Mr Bal Thackeray , supremo of the Shiv Sena, and accepted some cuts.... One of the characters in the film is a caricature of Mr Thackeray, shown as a prime mover of violence who, towards the end, looks aghast and repentant at the havoc he has wreaked. Mr Thackeray himself has objected to this scene, saying he is not repentant in the least." 

Senior journalist Vir Sanghvi had also expressed a similar view in one of the columns he had penned in 2010. Sanghvi had then written , "When Mani Ratnam's Bombay was released , Bal Thackeray objected on the grounds that the Thackeray character in the film was shown to regret the violence. 'I regret nothing ,' the Senapati declared. 'My boys took revenge on behalf of Hindus and I am proud of what they did." 

Sarkar (2005) was also released amidst a degree of controversy. The film's protagonist, played by Amitabh Bachchan, runs what looks like a parallel government. The Thackeray family watched the film in advance, although director Ram Gopal Varma denied that he had been forced to give the showing. Earlier, the director had also paid a visit to Thackeray and explained the character played by Bachchan to the Shiv Sena boss. Reports said that the Shiv Sena supremo had hugged director Varma after watching the movie. He had reportedly said, "You've captured my life so perfectly I can't believe this isn't my story!" 

Thackeray's real-life persona was also said to have inspired a character in literature. Salman Rushdie's first major effort after The Satanic Verses was the tome The Moor's Last Sigh, which featured the fictional Raman Fielding , who was painted as a star of the rightwing Hindu movement in Mumbai. Fielding is said to be a thinly disguised caricature of Thackeray.