I will speak of a few favourites only.
My no. 1 all-time super-duper favourite is "तू कहाँ ये बता" (tu kahan ye bata) from the 1963 classic "Tere Ghar Ke Saamne". In all likelihood, the song was shot in a studio set. But it captures the misty, rainy evenings that Shimla residents revel in yearly during the monsoon.
"हसीनों की सवारी है" (haseeno ki sawaari hai) from the 1960 film "Love In Shimla", a Mills-and-Boonesque romance, is a perennial favourite. This song captures Shimla's quaint rooftops, winding roads and dappled shade so wonderfully! A rare treat to see the Shimla of the 60s as the hero, Joy Mukherjee, runs past Shimla Club (didn't notice Chalet Day School which is located on the other side!), up to the US Club, then on to Ridge past Chris Church to reach Scandal Point.
No films based around Shimla would be complete without the hero yodelling the mandatory song in (or even on) the Kalka-Shimla train! "दिल थाम चले हम आज किधर" (dil thaam chale hum aaj kidhar) also from "Love In Shimla" has Joy Muhkerjee crooning in a first-class train compartment. In "मुझे अपना यार बना लो", (mujhe apna yaar banaa lo) from the 1960 film "Boyfriend", you have a jaunty Shammi Kapoor cadging a rooftop ride. Dangerous, but visually spell-binding!
Please click on the links to enjoy a moveable feast of Shimla! You may not understand Hindi, but the delights are all visual anyway...