As a québécois, I strongly suggest to watch Infoman (canadian politics satire, excellent way to stay informed on the federal level politics).

Also, some classics: “Dans une galaxie près de chez vous” (a show in the style of Red Dwarf, but targeting a younger public), “Le coeur a ses raisons” (a parody of soap operas), and even older “La ptite vie” (may not have aged as well, but depicts a typical Montreal family in the 80s)

For the hardcore, listen to François Pérusse “L’album du peuple”.

All these things can be watched and rewatched many times and will never get boring.