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The Sopranos may very well be my favorite show ever. I'd hate to compare it to my other contender, The Wire, because The Sopranos broke down all previously set conventions set a template for the modern HBO-esque drama.
At the risk of sounding pretentious, I find it strange to me that I hold this show in very high regard since I usually dislike watching shows at all; I find it difficult to commit to dozens of hours revolving around what I perceive to be the same, basic repetitive plotlines and characters.
The Sopranos isn't like that all; it's quality television, with each episode being almost like a movie on its own, and with the first two seasons being engaging, funny, and well produced. There is a great soundtrack from all conceivable genres and decades; couple with certain scenes, certain songs are associated with the show forever and the series even led to me listening to new musicians. The story is intriguing and there are actual stakes, and more so in the first two seasons; people are endangered and you get the feeling that anyone can die (and many major characters do).
The writing is its greatest strength, both in its complexity and realism. Unexpected, almost trivial moments and plot points are referenced and brought back throughout the show, while other elements sort of fizzle out. The dialogue in and of itself is witty and immensely amusing, heavily relying on dark humor, malapropisms and mistakes in speech that everyone can relate to, and is placed in contrast with death and drama.
The Sopranos is also a fascinating show to watch since it encapsulates American popular culture and society as it was before the turn of the millennium, during the aftermath of 9/11, and in the midst of the War on Terror.
However, as the series went on into the mid-2000s, the latter seasons grinded to a storytelling halt and devoted countless hours to boring, useless characters whose stories never went anywhere nor ended on a satisfactory note. This was an unfortunate side effect of the series' biggest sins; introducing far too many characters and thinking the audience cares about them. It's made even more egregious when by the end of the series, there is an entirely new, blank, and forgettable cast around a small number of great actors who were there from the beginning.
In spite of this, I don't regret watching The Sopranos. I consider it to be one of the greatest pieces of entertainment ever made and I felt like a different person after watching it, and I highly recommend it - it's on Amazon Prime in its entirety.
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