Ready To Die
Red and black lumberjack refers to a red and black checkered wool coat and the hat is made of matching material (and has ear flaps)
The champagne room, often "VIP Room", at a strip club is where dancers perform for a single customer for large sums of money. No matter what a stripper says, sex will not happen in this place.
Thank Me Later
Drake's simply saying he wants to live the 'good life' forever. So it is never ending.
It's the New Style
Licensed To Ill
He is stating that he has rolled a combination of marijuana and crack cocaine into a cigarette in anticipation of watching 80s police drama "Columbo" starring Peter Falk.