Top 10 Most Philosophical Rappers

The Top Ten
1 2Pac Tupac Amaru Shakur, also known as 2Pac, was an American rapper and actor born on June 16, 1971 in East Harlem, New York. Tupac sold over 75 million records worldwide and has been referred to in multiple major publications such as Rolling Stone as one of the greatest music artists of all time. 2Pac was assassinated on September 1996 at the age of 25. ...read more.
2 KRS-One Lawrence "Kris" Parker, better known by his stage names KRS-One, and Teacha, is an American rapper and occasional producer from The Bronx, New York City, New York.

From this guy, I only liked the instrumental version of his song ''A Friend''

3 Tyler, The Creator Tyler Gregory Okonma (born March 6, 1991), better known by his stage name Tyler, The Creator, is an American rapper, record producer, and music video director. He is well known for his hostile relations with his now deceased father, whom he addresses in multiple songs and albums telling the audience how much he distastes his father. Tyler has composed seven albums, which are Bastard (2009), Goblin (2011), Wolf (2013), Cherry Bomb (2015), Flower Boy (2017), IGOR (2019), and Call Me If You Get Lost (2021).

This rapper have some good songs, but are too rare for be honest.

4 CL Smooth
5 Aesop Rock Ian Matthias Bavitz, better known by his stage name Aesop Rock, is an American hip hop recording artist and producer residing in Portland, Oregon.
6 Rakim William Michael Griffin Jr. (born January 28, 1968), better known by his stage name Rakim Allah (or simply Rakim), is an American rapper and record producer. One half of golden age hip hop duo Eric B. & Rakim, he is widely regarded as one of the most influential and skilled MCs of all time. ...read more.

I'm not a such fan of Hip-Hop or Rap music, but I go with this Rakim
he got a really interesting Urban sense of humor.

7 Mos Def Yasiin Bey, best known by his stage name Mos Def, is an American hip hop recording artist, actor and activist from Brooklyn, New York City, New York.
8 Jay Electronica
9 Nas Nasir bin Olu Dara Jones, better known by his stage name Nas, is an American rapper and entrepreneur born on September 14, 1973 in New York City. His album, Illmatic, is considered to be one of the best rap albums of all time. He is also considered to be one of the best rappers of all time.
10 Lupe Fiasco Wasalu Muhammad Jaco (born February 16, 1982), better known by his stage name Lupe Fiasco, is an American rapper, record producer, and entrepreneur. He rose to fame in 2006 following the success of his debut album, Lupe Fiasco's Food & Liquor. He also performs as the frontman of rock band Japanese Cartoon ...read more.
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