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The first person to say, “party like it’s 1999” was likely the pop artist Prince, in his song “1999” from the album of the same name released in 1982.

This phrase was also perpetuated in the 2000’s due to the belief that the year 2000 aka Y2K would bring widespread network and system malfunctions causing serious repercussions and, as some people believed, effectively sending us back to the stoneage. Hence, people were partying pretty hard in 1999. As you can imagine, in 10 years time, people may very well be saying “party like it’s 2012” instead.

Also Pre-9/11 back in 1999 Computers Internet social Media and Terrorism didn’t exist to the point it does today life was much simpler back then we could ignore stuff and just party on.

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As a white rapper tackling issues of race, he is reluctant to get involved since it could alienate some of his fans as well as come off as tacky.

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While teenage pregnancies have steadily declined since the ‘80s, probably due to female birth control, lifetime rates of STDs among people under 25 have reached epidemic proportions.

If teenagers are getting pregnant less often but continue to get STDs at higher rates, it is condoms that must not be getting used.

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This is a common phrase in pop culture referring to the advances in health and medicine that allow people to live longer and look much younger than their age. 30 is not considered to be as old as it was just a few decades ago.

Jay-Z has a song, 30 Something, that expresses this idea and has made the phrase popular in Hip Hop.

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User macdaddyj pointed out an interesting play on words in the title of this track, “A Wake”.

Throughout the song, Macklemore emphasizes his spiritual “awakening” after a difficult time with drugs and alcohol in his own life. Now that he is “awake” to his own and others' foolishness, he is ending his old ways and finally putting his old life to death. This song represents the mourning of his past life, or in other words, a “wake”

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He regrets not doing more to win her heart and affection. If he would have just treated her right and let things happen on their own, the outcome could have been much different.

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In this phrase Maxwell is apologizing for the way he acted in the relationship. He is acknowledging the fact that he may have tried to force things that were never really there.

Instead of letting love take it’s course, he tried to convince her that they were in love before it truly happened.

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Maxwell realizes that he may not be the one to break down her walls completely and in turn is willing to let her go so that they can both find a better relationship in which they can thrive, or spread their wings.

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The image of holy water mixed with a gallon of sherm, or liquid PCP, paints a vivid picture. It represents the struggle between temptation and moral vice vs. righteousness. It is similar to the concept behind his song “Kush & Corinthians (His Pain)”.

I’m a loser, I’m a winner
I’m good, I’m bad,
I’m a Christian, I’m a sinner
I’m humble, I’m loud,
I’m righteous, I’m a killer
What I’m doing, I’m saying
that I’m human

Again, there’s a lot of this imagery on Kendrick’s Section.80 project:

As Kendrick attempts to point out again and again, even the most righteous can sometimes fall, and the path towards wickedness is never too far removed from the human condition.

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While “sherm” usually refers to a joint or cigarette dipped in PCP (Phencyclidine) – aka angel dust or wet – Kendrick seems to use it in reference to liquid PCP. Rather, “sherm-sticks” is the term most often used to describe the wacky tobacky laced with liquid PCP.

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