One of the most enjoyable subplots of Shantaram involves the Bollywood film industry - a world of colors, songs, romance, happiness, and dreams far removed from the typical Western movies of Hollywood. Indeed, as Lin points out, many Westerners find enjoying Bollywood movies to be difficult. They are too exuberant, too unrealistic. Yet, for Lin, they seem like the ideal cinema, a perfect foil for his romantic, passionate, vitally tragic inner life.
Bollywood began around the same time as Hollywood, with the first Indian movie (Raja Harishchandra) completed in 1913. The films grew in regional popularity through the sound era of the thirties and forties - difficult years for India that featured much political unrest. Bollywood movies were (and continue to be) primarily escapist, "universally" appealing films; the early Bollywood era, however, featured a more frank and risque treatment of sex. These pioneering films also occasionally featured political and social commentary.
The definitive shift toward a more homogenized, family-oriented cinema came, paradoxically, with the end of British rule in India. The Indian film critic Lata Khubchandani writes,"[O]ur earliest films...[had] liberal doses of sex and kissing scenes in them. Strangely, it was after Independence the censor board came into being and so did all the strictures." The post-British period also established several additional conventions that became near-universal in Bombay cinema: the dominance of the musical form (almost all Bollywood movies are musicals with catchy songs designed to sell pop records as well as movie tickets - we see this dual song/visual aspect of Bollywood repeatedly in Shantaram); long length (most Bollywood films last three hours and feature an intermission, a concession to the feeling among moviegoers that a film ought to give one one's "money's worth" or "paisa vasool"); and reliance on comforting, conventional plot twists (the star-crossed lovers, the scheming politician, the courageous youth, the hooker with a heart of gold).
This last aspect of Bollywood highlights the extent to which Roberts seems to have absorbed the lessons of the studios in putting together Shantaram. Like Bollywood movies, his novel is filled with unabashedly conventional figures. Ulla and Lisa are a couple of gold-hearted prostitutes; the legend of the courageous youth standing up to bandits (Seven Samurai-style) appears in the section in Sundar village; song and music is everywhere; villainous officials abound. Indeed, the upcoming adaptation of Shantaram, one might hope, may feature some sort of homage to Bollywood aesthetics.
Thanks to the internet, it's easier than ever to get into Bollywood as a Westerner. One resource for tracking down worthwhile films is the blog, bollyweird. There have recently been some prominent Bollywood/Hollywood and Bollywood/Broadway crossovers - such as Bride and Prejudice and, to a degree, Bend It Like Beckham - and those are obviously an ideal starting point in pursuing one's Bolly-curiosity. Gregory David Roberts, so he says in interviews, played bit roles in several Bollywood movies of the eighties, though there is as of yet no list of which those might be.