Never Call U Bitch Again.
I wouldn't say it's the number one most emotional song by him, but it's got a lot of feeling in there. I can really relate to it.

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I can't believe no one has said "My Block". That song was pure lyrical genius and it felt like he poured his heart into explaining the streets as real as they can get.

I would say his top 5 emotional songs are (in no particular order):

1. Unconditional Love.
2. Lord Knows (Demo Version). 2pac actually cries a bit at the end of one of his verses in this initial take.
3. Lil' Homies (Original Version). Just listen to the outro.I think it's about the most pissed off that 2pac can get.
4. Hit 'em Up. I would say that anger, as an emotion, is on full display in this song. Anger, rage, hatred, passion, excitement, aggression, are all in full swing.
5. When Thugz Cry (Original Version). I don't know of a deeper or more emotional song than this.I almost get emotional myself everytime I listen to this. And to think they BUTCHERED IT when they remixed it and put it out. This original version may very well arguably be the best solo effort he ever put forth.

Dear Mama
Run Bro! She Comin' To Kill Ya!

• Chance from "Real Chance Of Love"

Nice choice.
"It's gonna happen. All the people who change the world die in violence" 2Pac

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'life goes' on and 'unconditional love'
cinderella storyhere he goes cinderella boy.
Bill Murray- Caddyshack

life goes on!
Y'all nggs make sure it's popin' when we get up there
Don't front.
rip Tupac

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I like ghetto gospel, but Life Goes On always get to me, always brings me to tears.
"It's gonna happen. All the people who change the world die in violence" 2Pac

What about Ghetto Gospel? That's gotta be up there.

I agree that the 7 Day Theory album was his best. But, in my opinion, Life Goes On is his most emotional song. Everytime I hear it, I tear up.
The second runner-up song is Can U Get Away.
"It's gonna happen. All the people who change the world die in violence" 2Pac

Man Im surprised nobody has listed anything from his GREATEST album
Makaveli. This is where his poetry and his genius really shine. To date I have not heard better lyrics in a rap album.
But I digress, would vote White Mans World as his most emotional song:
"Dear sister
Got me twisted up in prison
I miss yah
Crying
Looking at my nieces and nephews picture
They say don't let this cruel world get yah
Kinda suspicious,
Swearing one day you might leave me
for someone thats richer
Twist the cap off the bottle
I Take a sip And see tomorrow
Gotta make if I have to Beg and Borrow
Reading love letters
late night, locked down, and quiet
If brothers don't receive their mail
Best believe we riot
Eating Jack mat
Staring at walls of Silence
Inside this cage
Where they captured all my rage and violence"
Simple, well versed, and poignant

Pain.
You know, I don't find this stuff amusing anymore

1. Dear Mamma
2. Life Goes On
3. Keep Ya Head Up
4. So Many Tears
5. Brenda's Got a baby

So Many Tears
Now that I'm strugglin in this business, by any means
Label me greedy gettin green, but seldom seen
And beep the world cause I'm cursed,
I'm havin visions of leavin here in a hearse,
God can you feel me? Take me away from all the pressure, and all the pain
Show me some happiness again, I'm goin blind
I spend my time in this cell, ain't livin well
I know my destiny is Hell, where did I fail?
My life is in denial, and when I die,
baptized in eternal fire I'll shed so many tears
My every move is a calcualted step
to bring me closer to embrace an early death
Now there's nothing left
Or Until The End Of Time
Perhaps I was addicted to the dark side
somewhere inside my childhood I missed my heart die
When my mama ask me will I change
I tell her yeah, but it's clear I'll always be the same
I am Jack's IMDB post.

Against All Odds. I really felt every word there. He named the people who tried to kill him and he let 'em know he ain't forgot. You could really feel his pain.

easy: Hit Em Up

dear mama.

Yesss!!! That song is pure fire indeed!!
"It's gonna happen. All the people who change the world die in violence." 2pac

Dear Mama

Hit' Em Up was a pretty emotional song, but if you want to hear the song with the most emotion, he sang Dear Mama once live where he messed up the lyrics. It's hard to tell but I read somewhere he actually was kind of tearing up. It's hard to tell, but here is the YouTube video on it.
http://www.youtube.com/watch?v=oWQ9xP1TwZ4

Hell Razor, pure fire from the soul esp the remix from sofly.