the first time I watched through TPB series it was through Netflix, and then I found out about all the companion films and the two 1999 B&W short films AFTERWARDS and always wished I watched it differently the first time around.
So I tried to put the timeline in chronological order of events and not when stuff was filmed (for example, the X-mas special was filmed after season 4 I think, but the events actually take place before season 1 as we get to see Ricky cause all the initial damage to the shitmobile.)
So I came up with this (please someone correct me if anything is out of place):
the Christmas special
the two 1999 B&W short films "Trailer Park Boys" and "The Cart Boy"
Seasons 1-5
Trailer Park Boys: The Movie aka The Big Dirty (which is in essence an "alternate timeline" of Season 5)
Seasons 6-7
Say Goodnight to the Bad Guys
Countdown to Liquor Day
Don't Legalize It
Seasons 8-9 (SOON!)