The Falcons Super Bowl Champion T-Shirt is a joke about how the NFL makes winning shirts for both teams in advance and donates the losing teams shirts to a 3rd world country
During Herr Starr's initiation process with the Grail, the song playing is "Blood on the Risers." "Blood on the Risers" is a paratroopers' song from World War II and is currently associated with airborne units of the the US military and other countries. It is the cautionary tale of a rookie who fails to check his parachute and dies with a splat.
The cubs winning.... which is referencing the Chicago Cubs finally winning the world series after 108 years.