Saddest Rap Songs

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The Contenders: Page 4

61 Keisha's Song (Her Pain) - Kendrick Lamar Keisha's Song (Her Pain) - Kendrick Lamar
62 Keep Ya Head Up - Tupac Keep Ya Head Up - Tupac

This song really help you through if you a single mother or going through abuse you know I love this song

63 No More - Will Smith No More - Will Smith

SO UNDERRATED JUST LISTEN TO IT. IT IS SO TOUCHING YOU WILL LOVE THE SONG. IT IS KINDA HEARTBREAKING. WILL SMITH IS A GREAT RAPPER DEFINITELY. HE MAKES GOOD SONGS NOT, GANGSTER STUFF. BUT SONGS FOR EVERYBODY THAT'S WHY HE IS WORTH LISTENING TOO. I DIG HIS MUSIC. PEACE OUT TO WILL SMITH BEST FLOW MUCH LOVE (;

64 Crew Love - Drake Crew Love - Drake
65 Goodbye - Slaughterhouse Goodbye - Slaughterhouse

Deep R.I.P. song. Each rapper from the group slaughterhouse had lost someone recently so they made this very emotional song in homage.

66 Like Toy Soldiers - Eminem Like Toy Soldiers - Eminem

This song is great, but is so much better once you know the whole story behind it (Google helps)

It's about how Bugz died because of rap beef, Em feels responsible. Fun fact: Proof portrays Bugz I'm the video, and is later killed

V 2 Comments
67 U - Kendrick Lamar U - Kendrick Lamar

Hello? how is this 96? kendrick beats himself up and destroys himself and all his pain and insecurity is so vivid and clear.

68 One Man Can Change the World - Big Sean One Man Can Change the World - Big Sean

This song is definitely the most powerful, soulful, and meaningful rap songs by one of the modern artists.

69 Tears to Snow - Hopsin Tears to Snow - Hopsin V 1 Comment
70 Lose Yourself - Eminem Lose Yourself - Eminem V 2 Comments
71 Airplanes, Pt. II - B.o.B Airplanes, Pt. II - B.o.B

Fantastic song. Eminems verse was my real eye opener about life. It taught me that if I ever want to accomplish my goals, I have to work for them, they wont just come to U. Seriously worth listening to, and deserves to be higher.

72 Choices (A Wave For Alex) - Charles Hamilton
73 Why - Nate Dogg

I'am sure that if any body listen that song will arrange it as nmb one.

V 1 Comment
74 November - Sadistik November - Sadistik

This is such a good song should be top 20 at least

75 Last Sad Song - Tech N9ne Last Sad Song - Tech N9ne

Very good song about Tech N9ne thinking about his singing and how people like his sad songs and how itll be his last one.

76 The Prayer - Kid Cudi

"And if I die before I wake, I pray to lord my soul to take." Need it say more?

Good enough to match up to Eminems best (This is comming from a die hard em fan)

V 1 Comment
77 Family Business - Kanye West Family Business - Kanye West
78 Rebecca - Grieves Rebecca - Grieves

Really great song. You should give it a listen

79 Letter to My Father - Caskey
80 Biggie Smalls vs Kanye West - Suicidal Thoughts

Its probably the best you can get should be top 10

Why isn't this #1? What?!

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List StatsUpdated 22 Jan 2017

3,000 votes
160 listings
5 years, 344 days old

Top Remixes (12)

1. Beautiful - Eminem
2. Mockingbird - Eminem
3. See My Tears - Machine Gun Kelly
Duggo38
1. My Block - Tupac
2. All I Do - Hishaam
3. Until the End of Time - 2pac
cleff
1. I'll Be Missing You - Puff Daddy
2. Difficult - Eminem
3. Good Die Young - D12
Mumbizz01

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