In chronological order,
1. Alam Ara(1931): This is a by-default entry in this list on the virtue of being ‘First ever Indian talkie’. Unfortunately, this movie has been long since lost and hence off course I haven’t seen it. Director Ardeshir Irani was just one of many directors trying to make a talking film and gauging its importance, made a conscious effort to finish it as soon as possible. After release, he turned out to be right as the movie turned out to be such a big hit, they needed police to control the crowds. But even in 1931, it wasn’t just talking; it was singing too and was 124 minutes long(Now you know why Indian movies are long or have songs).
2. Neecha Nagar(1946): Directed by Chetan Anand, it is one of the three films being credited for the rise of Parallel Cinema in Hindi film industry. Other two being Nagarik(1952)by Ritwik Ghatak which I have never seen and Bimal Roy’s Do Bigha Zamin(1953) which I have already written as an Essential film in Bollywood. So I guess I am giving Neecha Nagar its due credit by including it in this list, after all it is the oldest movie of three and was a winner of Grand Prize at Cannes. All these films also introduced the theme of neo-realism to the industry which became very much prevalent later in a lot of mainstream films as well.
3. Mother India(1957): First Indian movie to be nominated for the Oscar and it probably was the pinnacle of neorealism that Neecha Nagar introduced. The period from ‘40s to some early ‘60s is usually regarded as ‘Golden Age’ of Hindi cinema. Lot of movies which are still held to the highest acclaim were made during that time. As usual, I was trying to spread the wealth as much as possible in this list but this is 4th film from that period; there is a reason it’s called golden age. Mother India sometimes gets flacked for being too melodramatic and to tell you the truth, I even agree. But what makes it great is the accurate depiction of social and economic conditions in India at that time.
4. Madhumati(1958): If you watch this movie today, I am sure nobody will think world of this movie because, to tell you the truth, there is nothing extraordinary about this movie that you see on screen. What’s extraordinary is its legacy. There are hundreds of trivial things that we take for granted in horror films that were first used in Madhumati like inhibited mansion in the middle of nowhere, suspicious looking caretaker of that house who is the only living soul in miles, even something as trivial as cracking main door or the walking candle. I strongly believe that every single thriller, horror movie made since owes something to Madhumati.
5. Mughal-E-Azam(1960): In many ways, Mughal-E-Azamis Indian cinema’s Metropolis(1927). There is no connection with the subject matter but the first thing that comes to my mind about it is K. Asif’s epic vision. But that’s not the only similarity. Asif started working on this film in 1944. By the time it released, everything that can be changed about it was changed and it drove Asif to bankruptcy becoming the most expensive film then. However, he always kept his eyes on the target and relentlessly pursued it, to the last detail. He also made sure it never became style over substance. As a result, there are not many films even today that have such an epic scope but still have solid cinematic foundations. 
6. Sholay(1975): No list talking about the greatest movies in Bollywood can be complete without the inclusion of probably the most iconic Hindi movie of all time. What the hell! Why do I even need ‘probably’? It is THE most iconic Hindi movie of all time. I really don’t think there are many people who’ll think of that as going too far. Sholay is just that solid. 1975 was a great year for Bollywood. There are few more films that year that left their mark on the industry including Deewaar(1975). In 1975, Deewaarwas a bigger hit; it won most of the awards over Sholay as well. But after so many years, I think not only Sholay has endured the test of time better but it has contributed more to the industry to substantiate this place. 
7. Mr. India(1987): Of all the films on this list, this is probably the least expected film to appear on such list but I think it is worth that honor. Despite being a very mainstream film with every aspect of a typical ‘Masala’ film present, this is probably the only example Sci-Fi film done right in the industry. Yes, I called it a sci-fi film. Well, the man disappears! So, if Hollow Man(2000) is sci-fi, so is Mr. India. I can think of many other movies that attempted this genre but in my opinion almost every single one of them fails miserably. The fact that Shekhar Kapur at least successfully entertains you in Mr. India is enough for me to put it in this list. Add on one of the most iconic villain and Hawa-Hawai to it and I am sold.
8. Dilwale Dulhaniya Le Jayenge(1995): Since '90s, a typical Bollywood movie can be summed up as a ‘Family-centric Romantic Musical’. I know that is lot of genres together but on an average, any Hindi film fits into about 5 genres. So bear with me. In my opinion, success of DDLJ played an instrumental role in shifting the pendulum towards it. In the intro, I said that these movies changed the industry, for better or for worse. In the hindsight I think what followed it was for worse but I am not about to blame this movie for incompetence of those who tried to cash-on its success. It does have its weaknesses, I won’t deny that but if you want to watch a typical Bollywood masala movie, why not go for the best? That’s Dilwale Dulhaniya Le Jayenge for you. 
9. Satya(1998): There aren’t many movies that can boast something Satya can – it made it necessary to introduce whole another genre in the industry. Mumbai Noir. Ramgopal Verma’s Satyais first gangster movie made in Hindi. This legacy alone guarantees it a spot on many lists, executing it as well as it does was just an added advantage to solidify its position in the history of Hindi cinema. Genre made popular by the likes of Francis Ford Coppola and Martin Scorsese came to India in the form of Satya and I don’t know if it reflects positively or negatively on the industry but despite many other movies made since, it still remains to be ‘the best’.
10. 3 Idiots(2009): This movie is Bollywood equivalent of Fight Club(1999) for me because I might be one of 7 people on this earth who have seen this film and does not think that it is the greatest thing in the world. In my opinion it goes way too over the top too many times to take it seriously. But at the same time I cannot deny the fact that this is the highest grossing movie of all time, first one to cross INR 1 billion mark and the reason it’s on the list – to open many overseas markets for Indian movies. It’s not the first time Indian movies have had success overseas; Karan Johar has been making movies exclusively for that market since late ‘90s but none did the business like this one did and I believe 3 Idiotsis an important reason why there have been film festivals going on in Japan or regular releases of Hindi movies in many other markets of East Asia.
