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One Last Shot (1998)
Precursor to Trailer Park Boys
So this film is precursor to TPB. Robb Wells stars as Robb and John Paul Tremblay as Gary William aka GW. John Dunsworth plays Mr. Lahey who happens to be GW's boss. The film and characters aren't the greatest and there's definitely a lot of fleshing out certain details and characteristics between One Last Shot and the debut of Trailer Park Boys. But this is no doubt where it began.
Available on Netflix Canada at the time of this writing (September 2018).