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Best is Relative: Our 10 Best Rap Songs, By Occasion

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uptown 10 best rap songs

For the past 25 years since its “formal introduction” to the masses via Billboard‘s Hot Rap Songs chart, rap music has evolved into what could be described as one of pop culture’s load bearing walls.

Music provides background to many of our life’s greatest memories and just like all genres, rap is no different. How many summers do you remember not by the calendar year but by anthem? What you listened to while unsuccessfully break dancing on cardboard boxes, how you got your head right before a high school track meet, or to get through all night study sessions in college.  It was also an anxiety blocker while getting ready for day 1 at your first corporate job, and it was what made you ‘get low’ in the club.

Whether its fans were looking out the windows of the projects in the Big Apple or on the streets of Compton, learning to navigate “the streets” and corporate America, Rap music has penetrated even the most remote pockets of the world.

After Monday’s head scratching revelation that Macklemore & Ryan Lewis “Thrift Shop” is the No. 1 rap song of all time (according to Billboard) we realized that ‘best’ is relative, and is truly in the eye of the beholder.  Feeling inspired, I compiled a list of 10 Rap Songs that are ‘bests’ in their own right because they’re reminders of life’s universally relatable moments…breakups, rainy days, summoning motivation and more.


Best Rap Song To Get Over A Breakup
“Lost Ones” - Lauryn Hill


Best R.I.P Rap Song
“They Reminisce Over You (T.R.O.Y.)” - Pete Rock & CL Smooth


Best Theme Song For Girls’ Night Out
“Ladies Night” – Da Brat, Left Eye, Missy Elliott, Angie Martinez, Lil’ Kim

Best Rap Song To Get Dressed To Before You Go Clubbing
“Change Clothes” - JAY Z


Best Rap Song That Will Cheer You Up On A Rainy Day
“Keep Your Head Up” - 2Pac


Best Rap Song That Belongs On Your ‘In The Mood’ Soundtrack
“Poetic Justice” – Kendrick Lamar


Rap Song That Your Aunties And ‘Nem Say Is Their Jam
“The Humpty Dance” - Digital Underground


Best Rap Song To Get The Party Started
“It Takes Two” – Rob Base and DJ E-Z Rock


Best Rap Song To Apologize With
“One More Chance” – Notorious B.I.G


Best Rap Song For Motivation
“Lose Yourself” – Eminem


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