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For me, Moulin Rouge! was the first movie I saw that piqued my interest in musicals in general, and as such holds a special place in my movie-watching pantheon. It had to appear on this list.

2. West Side Story

When I listed my favorite movies about New York, I explained that I listed West Side Story, one of my favorite movies of all-time (if not “the”), because there was another movie that was more “about” New York than this one. Today, I don’t really have such an explanation for my #1 and #2 picks other than wanting to leave a little suspense for the top choice again. By now, of course, if you picked up on the Russ Tamblyn and Robert Wise hints from earlier in the list, you were expecting the 1961 Best Picture winner (a total of 10 Oscars total, one shy of the all-tie record) to be on the list.

And why not? It has a lot of what one sees in Seven Brides (the ensemble numbers, the plot-advancing songs) and then some. Who else other than Stephen Sondheim could pen such beautiful lyrics to go along with the touching, at times haunting, and always smile-inducing score by Leonard Bernstein. The talent involved in making this film is unrivaled, and the modern-day take on the Shakespeare classic was as timely in the 1960s as it is today. Expect this movie to appear over and over again on the A-List, it is hard to run out of new things to say about it.

1. Cabaret

But I saved the number one spot for another old-time classic, the unsurpassed Bob Fosse musical, Cabaret. Like Sound of Music and West Side Story, Cabaret is notable for some of its Oscar history. It holds the record for most Oscars won (eight) without winning Best Picture. One can hardly blame it for losing that prize to a movie you may have heard of called The Godfather. It did, however, defeat Coppola for the Best Director award (which he would win later for the sequel anyway). And, like the Sound of Music, this movie uses the tension and bleakness surrounding the Nazi ascent of power to move its plot forward. If you sense a theme it is because there is one: remember that these stories were all written in the immediate aftermath of the war.

Cabaret does everything right that all the other movies on this list do: the music is outstanding, the acting by the lead cast is unparalleled (netting acting Oscars for Liza Minnelli and Joel Grey as Sally Bowles and the emcee, respectively), and the technical aspects of this movie (in this case, the set decoration, costumes, and lighting) are perfectly suited for the movie’s tone, and a work of art in and of themselves.

But what makes Cabaret head and shoulders above the rest of them is that it also contains subtle social commentary, and an honest assessment of the meanings and challenges of love and life. Cabaret was groundbreaking in its portrayal of a gay character in the early 1970s, and anxiety-inducing in its cynical assessment of the expediency of the human condition. Unlike most of the other movies on this list, it is unforgiving, and does not look for a happy ending or an easy resolution. By now, you may have noticed that I tend to prefer the more challenging movie than those that gift-wrap a smile for the audience in the end.

In any case, I leave with a smile every time I see this movie. Perhaps not because of happily ever after, but simply because of the cinematic talent that went into its production, and because of how the gut-wrenching aspects of the story challenge one to be introspective about our own views of love, its challenges, and its tragedies.

A brief programming note is in order. This month, I will return with “They Shoot Oscar Prognosticators, Don’t They?”, as awards season begins with the Telluride and Toronto Film Festival. I will endeavor to continue the A-List, but as Oscar coverage increases the former will naturally decrease in turn.

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