“The Last Of The Real Ones”

LYRICS: “My head is stripped just like a screw that's been tightened too many times”
WHAT IT MEANS: “Stripping a screw” is over-tightening a screw to the extent that you damage the rivets. According to Genius user viawentztop, “a ‘damaged head’ would metaphorically refer to a volatile mind or mental state, which he claims to have been caused by trying to be fixed too many times.” 

“Tell That Mick He Just Made My List Of Things To Do Today”

LYRICS: “Light that smoke, that one for giving up on me/And one just 'cause they’ll kill you sooner than my expectations”
WHAT IT MEANS: A overt reference in the film Rushmore (where this song also gets its name), this line encourages the listener to light up and reminisce on giving up on the speaker. According to Genius user furiousstyles, “Telling her that the cigarettes will kill her ‘sooner than my expectations’ implies sarcastically that she couldn’t love him the way he needed, or live up to what he wanted.” 

“20 Dollar Nose Bleed”

LYRICS: “It's not me, it's you/Actually, it's the taxidermy of you and me”
WHAT IT MEANS: The first section is a flip on the cliched breakup line, “It’s not you, it’s me.” A taxidermy is a stuffed corpse of an animal, so its use here implies the relationship has been dead for a while, and they have merely been a corpse on display. 

“Headfirst Slide Into Cooperstown On A Bad Bet”

LYRICS: “Aw, Tempest in a teacup/Get unique”
WHAT IT MEANS: As stated by Genius user actionboy99: “A ‘storm in a teacup’ is to be upset or excited about a trivial matter.” A tempest is a storm of considerable size and strength. 

“Sophomore Slump Or Comeback Of The Year”

LYRICS: “'Cause I swear I'd burn this city down to show you the light”
WHAT IT MEANS: Genius user viawentztop says, “Lights of cities cause light pollution to the sky, which can block out the stars. By saying he will ‘burn down the city’ means how he would be willing to go great lengths to make her truly happy.” 

“27”

LYRICS: “I've got a lot of friends who are stars/But some are just black holes”
WHAT IT MEANS: Black holes are sections of space which are so dense, no light can get out. This often happens when stars die. Here, the speaker plays upon the “star” as a Hollywood concept—they might have friends who are famous, but when they die, they will suck all their friends into a black hole.