Gauchos, not “douchos” or Goucher — a famous Harlem basketball team.
Also a Caddyshack allusion, given the preceding reference to golf.
The losing team in Hoosiers is all black; the winning team is all white. Many blacks have expressed some unease with this subtext, including Spike Lee.
That’s “blue steel” — a gun, and probably a Zoolander reference too
Once again, the GZA reference is an attempt to establish his hip-hop bonafides.
Drake uses lines like this to show that he is still connected to that “real” hip-hop, despite the fact that he rattles off pop hits with R&B choruses to pay his (substantial) bills.
Beating a dead horse — no sense dissing a guy with no career.
The “hidden” reference to Pete Rock is appropriate, since Drake is rapping about how he has to keep his street/underground side hidden to sell records and please his label.
Key context for the title: in 1990 NWA released a song called 100 Miles and Running which featured numerous jabs at former associate Ice Cube. Game, who never fails to proclaim his allegiance to Eazy-E and Dr. Dre, sees himself as being in the same position, and appropriates the name of their track for his own.
Goes with the Mike Jones reference.