What's the saddest song in rap history??

[TraceOneInfinite Flat Earther 96']

Great tracks that will make you cry?

"World So Cruel" Flesh

"White Man's World" Pac

"Timelock", "Worldly Ways", "Lil Buddy" - Slim Calhoun

what else?

[Sccit]

nothing comes close

[BJV]

[Ebony Bree Caple]

Last Time Boot Camp Clik

[TraceOneInfinite Flat Earther 96']

Last Time Boot Camp Clik

"Last Time" Bad Azz

[Duck Duck Doggy]

Eminem - Kim

[Jay_J]

Pigeon John - Emily
Dr. Dre - The Message
Jedi Mind Tricks - Before The Great Collapse/Razorblade Salvation
Nate Dogg - Why
2pac - I Ain'T Mad At Cha

[D-TalkX]

Renee - Lost Boyz

[dnjp4life]

Some music can be so powerful that it can almost bring you to tears if it hits you right, even if the subject matter of the music itself is not sad.  When I first heard the gospel intro to Kanye's Jesus is King album it hit me in a real way, similarly Nate Dogg's track Never Too Late always leaves me feeling some sort of way when I listen to it, and Sky's the Limit by Biggie too.

DMX's Slippin is gut-wrenchingly sad, as is Kendrick's Sing About Me, I'm Dying of Thirst, and one of his tracks on To Pimp a Butterfly, I forget the name of it.  Eminem's song Beautiful is quite depressing, he has a lot of sad stuff really, Freddie Gibbs' track Situations is very downbeat, obviously anything to do with death and losing someone close like Slaughterhouse's Goodbye is bound to be a sad listen.

Whenever I find myself listening to 2Pac's Untouchable freestyle I always get kinda sad, it always feels to me like he's on top of the rap world and he knows it, and he's drunkenly celebrating the fact, but at the same time he's aware that he hasn't much time left.  It almost has the feel of it being 2Pac's last recording, even though I know it's not.  I wonder if anyone feels the same way when listening to it?

[TraceOneInfinite Flat Earther 96']

Renee - Lost Boyz

^^this^^ that’s my joint right there... Used to wait for it to come on YoMTVRaps after midnight Feb 96

[Rubinho]

Got to check some of the above ones, most are in my playlist though.
Eve - Love is blind
D12 - Good die young
Master P - Dead Homies (not sure about this track name)

[TraceOneInfinite Flat Earther 96']

Got to check some of the above ones, most are in my playlist though.
Eve - Love is blind
D12 - Good die young
Master P - Dead Homies (not sure about this track name)

D12 - “Good Die Young” was my favorite song on that album.  Actually that was the first album where Eminem showed signs of slowing down.  Still a good album but not to the standard of perfection in everything he did from Slim Shady EP thru 8 Mile

[thegooddoc]

Lord Knows  - 2PAC
How Long will They Mourn Me - Thug Life
Pain - 2Pac ft. Stretch
Never Seen a Man Cry - Scarface
Ever So Clear - Bushwick Bill

[TraceOneInfinite Flat Earther 96']

Lord Knows  - 2PAC
How Long will They Mourn Me - Thug Life
Pain - 2Pac ft. Stretch
Never Seen a Man Cry - Scarface
Ever So Clear - Bushwick Bill

Yeah definitely the 2pac songs u mentioned

[Soopafly DPGC]

Definitely agree with all mentioned. I’d throw in:

RIP Mausberg by DJ Quik. Literally sounded like he was in tears rapping his verse.