I had a friend who once recommended Om Shanti Om as a good gateway movie into Bollywood. I both agree and disagree with that choice. It's a movie that pays tribute to Bollywood's heritage, particularly from the 70s but is also set in the modern day era. It's sort of a cinematic throwback and features all the major Bollywood genres packed in one film (musical, romance, drama, comedy, action, revenge thriller, etc.)
The only minus for a newbie is that the movie is filled with easter eggs, references, and cameos to the Bollywood film industry so all of that would be lost on you. But I don't think that would detract from your viewing experience. When the movie came out, I didn't understand the references to all the older movies (I did understand the contemporary references though) but still enjoyed it.
Om Shanti Om also has the advantage of featuring the biggest Bollywood star, Shah Rukh Khan, as the male lead. While the female lead, in her debut film, is Deepika Padukone, currently the #1 leading lady of Bollywood and a superstar herself. He's probably the best known Indian public figure in the west and she's one of the better known Indian actresses globally.
If not Om Shanti Om, I would recommend any film with Shah Rukh Khan because he epitomizes Bollywood (and India by extension) in the west. His movies in particular are beloved overseas, more than his contemporaries' movies, so SRK is usually the entry point for new fans of Bollywood.
Kabhi Khushi Kabhie Gham is the most popular Bollywood movie overseas (also the most watched Bollywood movie on Netflix) starring an A-List cast including SRK as lead. It's a family drama entertainer which was a really popular genre in the 90s/early 2000s. It's a tearjerker though and 3.5 hours long, which is long even by Bollywood standards. Tbh, I never noticed it was that long a film but for someone new to Bollywood, you may feel it.
If not Kabhi Khushi Kabhie Gham, I would recommend Dilwale Dulhania Le Jayenge or Kuch Kuch Hota Hai. All three of these films star SRK with Kajol, his most beloved heroine and a name synonymous with him. Dilwale Dulhania Le Jayenge is one of the most enduring film classics and still plays in theaters to this day despite coming out in 1995, making it the longest running movie to play in theaters. It reinvented the romance genre and pretty much every film that came afterwards owes its legacy to DDLJ. It's also a good entry point for westerners because it's the movie that launched SRK as a superstar and features the clash between eastern vs western values. I think it was the first prominent Bollywood movie to be set outside of India and portray the lives of NRIs (non-resident Indians who live overseas).
Kuch Kuch Hota Hai is sort of a spiritual successor to DDLJ (just as Kabhi Khushi Kabhie Gham is a spiritual successor to Kuch Kuch Hota Hai). This is also one of the most popular movies overseas (#3 most watched Bollywood movie on Netflix) because the first half of the film features the characters as college students and is heavily inspired by the Archie/Betty/Veronica comics. Another tearjerker melodrama.
And if you want a movie that isn't set in India at all but set in America, then I would recommend Kal Ho Naa Ho. Another one of the most beloved Bollywood movies overseas (the #4 most watched Bollywood movie on Netflix) and this one might be easier to start off with because of it's NYC setting and featuring NRIs.
If you prefer action over romance, then I would recommend Main Hoon Na, which is the 2nd most watched Bollywood movie on Netflix. SRK plays an Indian army major who goes undercover into a college. So it features the college shenanigans that are also in Kuch Kuch Hota Hai along with family dynamics, plus a pro-peace message between India vs Pakistan. There is still romance but it's not the central premise of this movie unlike the others I mentioned.
Finally, if you're really daring, you could start off with Devdas. This is a Bengali period novel that's considered part of India's classic literature. All the films I suggested before have heavy western influences since they're all set in contemporary times (90s/2000s) with heavy globalization, but that's not the case here as this is set in the early 1900s.
But if you want a pure, unadulterated Bollywood experience, this is the one that probably is the most authentic depiction of India. This was also the west's first exposure to Bollywood because Devdas was heavily promoted overseas, particularly in Cannes and all the film festivals. You might recognize Aishwarya Rai, the lead actress, who also came to Hollywood after the success of this film and was called the most beautiful woman in the world.
So Devdas might actually be the best choice as a gateway film into Bollywood since it's probably one of the most iconic films that was released in the last 25 years. It's music, dances, and performances are a part of pop culture and I've even seen Devdas referenced a lot in the west (Big Bang Theory features a reference to it for example). You mentioned being really interested in Indian culture and history so that would probably make this the best starting point.
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