This refers to Redman and Method Man, who collaberated and released a couple of albums in thier time. They did freestyle on stage back in the early 1990’s, but he wonders if they had been enemies like 2pac and Biggie if that would have driven more out of them as artists.

He is a young man with issues: he has already been to prison on charges on multiple occasions, he hasn’t seen his mother in a week, (which may show the sign of either a huge fight between them or a sudden change in his personality which means he is not in touch with his old life as a young kid), and he hasn’t seen his dad in a longer time, (which means he didn’t really have a stable father figure and doesn’t know some of the ways to be a man and act suitable), and he is heading down a path that will lead him to an arly death in which he will never realize his true potential in life. He doesn’t show his fustration with all of this but keeps it bottled up to the point of extreme depression, longing, and deep pain.

A little bit of a reference to rapper Drake’s song “Started From The Bottom”.

The song is the perfect feeling for Wale. A rappers dream of making it big even though he had a terrible starting point in the hood but was still able to realize his goals in music and in life.

Blessings could be referring to money and whoever preaches probably wants their monetary gain to increase so they can supprt themselves and their family. Blessings could also refer to anything they already have but they want it to get better like family relationships or job security.

He’s high above everybody else and more talented than the rest of his competition. This could also mean he is high as in on drugs as he is famous enough to generate money to buy such things.

This line could also be a continuation of the car line and referencing the trips he takes on a plane on tour.

The moment Cudder fans have been waiting for. “Guilt Trip” marks the fifth consecutive Kanye project where Cudi’s done a guest bridge or hook. This trend has kept going on ever since 808s & Heartbreak:

• 808s & Heartbreak: “Welcome To Heartbreak”

• My Beautiful Dark Twisted Fantasy: “Gorgeous” & “All Of The Lights”

• Watch the Throne: “The Joy” & “Illest Motherfucker Alive”

• Cruel Summer: “Creepers” & “The Morning”

• The Life of Pablo: “Father Stretch My Hands Pt. 1” & “Waves”

• ye: “No Mistakes” & “Ghost Town”

In 2014, after the release of his own album, Cudi himself said that this interlude was not recorded with Kanye and was years old:

The vocal that I did on that song was a couple years old. I forgot which session it was, part of me was flattered, like, it’s kind of cool that he thought of me. Then I started thinking about it more. It was like, Why not call me and have me come in there and give it? Why underuse me? Why put four bars of vocals to coax my fans into thinking this is a legitimate Kid Cudi feature on this song and it isn’t? I don’t know how to feel but I would’ve much rather been off that song. I don’t care to be on people’s songs like that. Unless it came from a legitimate session where we’re all vibing and have an idea.

This might be a reach but seeing as to how the songs name is “Guilt Trip” and the lyrics Kanye used for Cudi’s interlude “If you love me so much why’d you let me go” It could be possible that Kanye resents letting Kid Cudi leave, considering the well-dispersed public knowledge that him and Cudi had a good relationship.

This sample is from the song “1979” by The Smashing Pumpkins and it describes the life XV lives: He lives it to the fullest by the spur of the moment and doesn’t care what happens until he dies. This is not the first time XV used The Smashing Pumpkins in a song.