When Does "The Sopranos" Season One (1999) Take Place?
"The Sopranos" season one is a crime television series showran by David Chase that released January 10th, 1999. So when is "The Sopranos" season 1 set?
It takes place in the year:
We know this because in season 1 episode 1 "The Sopranos" a printed issue of the real-world newspaper "The Star Ledger" is delivered to Tony Soprano's driveway, "The Star Ledger" was named "The Newark Star-Ledger" until May of 1964 AD, and it ceased making a print edition in February of 2025 AD. So it must be between May of 1964 AD and February of 2025 AD.

1998 AD
We know this because in season 1 episode 1 "The Sopranos" a printed issue of the real-world newspaper "The Star Ledger" is delivered to Tony Soprano's driveway, "The Star Ledger" was named "The Newark Star-Ledger" until May of 1964 AD, and it ceased making a print edition in February of 2025 AD. So it must be between May of 1964 AD and February of 2025 AD.
More specifically, the issue in the first episode has a front page dated for "WEDNESDAY, JUNE 17, 1998".
This front page includes the headline: "Clinton Warns Medicare Could Be Bust in Yr 2000" and United States of America President Bill Clinton made protecting the government medical insurance program Medicare a major issue throughout 1998 AD and 1999 AD in the real-world.