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Tupac Shakur’s 10 greatest songs of all time

Today marks what would have been Tupac Shakur’s 49th birthday.

Tupac Amaru Shakur, born Lesane Parish Crooks, wasn’t just a rapper, actor, model or entrepreneur, he was a game-changing icon of music, poetry and street life. He was the first gangster rapper to come equipped with a message, a heart, and the emotional foresight to see it wouldn’t last forever.

Wrapped in mystique following his tragic death in 1996, Tupac may well have become the face of a generation, espousing societal theories as quickly as he spits gun bars, but above everything else, 2Pac was an incredible artist.

With a landmark in our laps, we thought we’d challenge ourselves to whittle down the rapper’s incredible and varied back catalogue into his ten most essential songs. Featuring tracks from before and after his death, it’s clear to see that 2Pac will be remembered forever.

Unlike any other rapper, Tupac was able to be at once vulnerable and armoured, at once throwing a punch while showing his scars, and the below songs all reflect this duality, the fallibility and humanity of an artist gone far too soon.

Tupac’s 10 best songs:

10. ‘Papa’z Song’ – Strictly for my N.I.-.-.A.Z

Had to play catch by myself / what a sorry sight / A pitiful plight / so I pray for a starry night / Please send me a pops before puberty / The things I wouldn’t do to see a piece of family unity.”

Within the opening seconds, Tupac speaks for a nation of fatherless children. ‘How can I be a man if there’s no role model,’ he continues as he spits over a sample of ‘Soul Shadowsby The Crusaders ft Bill Withers. Joined by Pac’s stepbrother: Mopreme, both express their disappointment with the lack of a constant father figure and the struggles of a single mother in black America.

Mopreme sneers through the second verse: ‘Moms had to entertain many men / Didn’t wanna do it but it’s time to pay the rent again / I’m gettin a bit older and I’m startin to be a bother / Moms can’t stand me cause I’m lookin like my father.’ The song strikes home the effect an absentee father has on the family unit. 

9. ‘So Many Tears’ – Me Against the World

Now I’m lost and I’m weary / So many tears / I’m suicidal so don’t stand near me / My every move is a calculated step / to bring me closer / To embrace an early death / now there’s nothing left.

Towards the end of his 25 years, Pac was wary of those close to him. He claimed his one-time friends Biggie and Puffy had set him up. The Bad Boy Entertainment rappers continuously denied this but managed to prod a stick into the hornets’ nest when, whilst 2Pac was incarcerated for his part in an alleged sexual assault and still bearing five fresh gunshot wounds from the robbery in a New York recording studio in which Bad Boy and Uptown Records artists were expectantly waiting for Pac upstairs, The Notorious B.I.G released a track titled ‘Who Shot Ya?’

Talk about bad timing! Once Pac was released, (He signed a contract with Death Row Records for bail money,) he went at Bad Boy with all he had, sometimes subliminally, other times directly.

‘So Many Tears’ is taken from Me Against the World. In the album, released in ’95, Pac takes on a more thoughtful and darker tone than his previous releases. Struggling with paranoia and the aftermath of being shot during the Quad Recording Studio robbery. This personal and reflective album debuted at number one while he was still incarcerated, beating Bruce Springsteen’s Greatest Hits.

8. ‘Dear Mama’ –  Me Against the World 

And even as a crack fiend, mama / You always was a black queen, mama / I finally understand / For a woman it ain’t easy trying to raise a man / You always was committed / A poor single mother on welfare / Tell me how ya did it / There’s no way I can pay you back / But the plan is to show you that I understand / You are appreciated.

The first and most successful single from Me Against the World shows Tupac paying tribute to his mother, Black Panther Activist and ex-addict: Afeni Shakur. Using a sample of ‘In All My Wildest Dreams’ by Joe Sample, Pac croons over the beat with a harsh and open sadness contrasted by an emotional softness that few rappers had attempted before.

It remains an excellent introductory track to 2Pac. 

7. ‘Trapped’ –  2Pacalypse Now

They got me trapped / Can barely walk the city streets / Without a cop harassin’ me / Searching me / Then askin’ my identity / Hands up / throw me up against the wall / Didn’t do a thing at all / I’m telling you one day these suckers gotta fall.

Featuring a barely recognisable sample of James Brown’s The Spank, Trapped’s first verse tells the story of a black man’s experience at the hands of police brutality. It was the first single off his debut album, back when the 2Pac logo was stylized as a handgun and featured Digital Underground’s Shock G on background vocals.

Shortly after the video was released, Tupac was beaten unconscious by Oakland Police Officers after being stopped for jaywalking. He bore the physical scars on his face until his death.

6. ‘Changes’ – Greatest Hits 

“I’m tired of being poor and, even worse, I’m black / My stomach hurts so I’m looking for a purse to snatch / Cops give a damn about a negro / Pull the trigger, kill a n-gga, he’s a hero / “Give the crack to the kids: who the hell cares? / One less hungry mouth on the welfare!”

Released posthumously and featuring vocals taken from ‘I Wonder if Heaven Got a Ghetto’. Changes is one of the more referenced Tupac songs. The scathing lyrics take well-placed shots at the police and government, reminding us of the murder of Black Panther founder: Huey P. Newton, and a narration of what it is like to be an underprivileged black youth in Ghetto America.

2Pac is angry and frustrated at the lack of support and changes in the community. The final bars eerily predict his violent demise: “And as long as I stay black / I gotta stay strapped / And I never get to lay back / ‘Cause I always got to worry ’bout the payback / Some buck that I roughed up way back / Coming back after all these years /”Rat-a-tat-tat-tat-tat!” / That’s the way it is.”

5. ‘California Love’ – All Eyez on Me

Out on bail, fresh out of jail, California dreamin’ / Soon as I step on the scene, I’m hearin’ hoochies screamin’ / Fiendin’ for money and alcohol, the life of a Westside player / Where cowards die and the strong ball. 

After signing a three-page handwritten contract behind bars in order to secure his bail money. The newly released Shakur was about to prove his worth to new label CEO: Death Row Record’s Suge Knight. Pairing with Dr. Dre who also produced both this and hip-hop banger: ‘Can’t C Me’. 2pac’s return to the mainstream was epic. ‘California Love’ (and its several incarnations,) remains as fresh today as it was in 1995. Shake it, Cali!

4. ‘Hit ‘Em Up’ – Greatest Hits. 

Now when I came out, I told you it was just about Biggie / Then everybody had to open their mouth with a mother-cking opinion / Well this is how we gonna do this / F-ck Mobb Deep, f-ck Biggie / F-ck Bad Boy as a staff, record label and as a motherf-cking crew / And if you want to be down with Bad Boy, then f-ck you too.”

Wow, where to start. Perhaps the most brutal 2Pac song there is. Attacking several East Coast rappers whilst aiming the brunt of his fury at Bad Boy Record’s Notorious B.I.G and Puff Daddy, who Shakur believed were behind the robbery and shooting in Quad Studios (Puffy and BIG were present upstairs at the studio during the incident.)

In the opening seconds, he claims to have slept with Biggie’s estranged wife: Faith Evans, then proceeds to rip the label and its associates apart. Pac was joined by the Outlawz, who each chipped in with the verbal bashing of foes. The accompanying music video featured caricatures of Puff, B.I.G and Lil Kim, and was as brutal as the venomous lyrics.

In a further smack in the mouth for Bad Boy, the Johnny J produced track used samples of Junior M.A.F.I.A’s ‘Get Money’, here changed to ‘Take Money,’ and allegedly featured Faith Evans on some of the vocals. No stranger to controversy himself, Public Enemy’s Chuck D later went on to say Tupac had gone too far with the song.

3. ‘Letter 2 My Unborn’ – Until the End of Time.

Dear Lord, can you hear me / Tell me what to say / To my unborn seed in case I pass away / Will my child get to feel love / Or are we all just cursed to be street thugs? / Cause bein’ black hurts.

It’s far too easy to label Shakur as a Gangsta Rapper, although for a short period of his life he did play that role to great effect, but he was also a poet, an actor and an activist. He showed a sensitive, caring side that very few rappers dared to bare. Using a sample of Michael Jackson’s ‘Liberian Girl’, ‘Letter to My Unborn’ is an autobiographically poignant and heartfelt ode to Pac’s unborn child.

He reflects on his troubled life and addresses death directly whilst warning his potential offspring of the dangers that await. Released posthumously, the 2001 track remains one of the better post-death songs.

2. ‘How Long Will They Mourn Me?’ – Thug Life: Volume 1. 

All my homies drinkin’ liquor / Tears in everybody’s eyes / N-ggas cried / To mourn a homie’s homicide / But I can’t cry, instead I’m just a shoulder / Damn, why they take another soldier?

Co-produced by Warren G and featuring vocals by the legendary Nate Dogg. How Long Will They Mourn Me was the highlight of Thug Life’s only studio album. Recorded shortly after the death of 2Pac’s friend: Kato, he invited the rest of Thug Life to join him in paying tribute.

The song was re-released in its original incarnation in September 2019, the albums 25th anniversary and featured alternative lyrics. Unfortunately, the revamped track, although similar in composition to the album version, does not have the same lyrical impact on the listener.  

1. ‘Keep Ya Head Up’ – Strictly for my N.I.-.-.A.Z

“I think it’s time to kill for our women / Time to heal our women, be real to our women / And if we don’t, we’ll have a race of babies / That will hate the ladies that make the babies / And since a man can’t make one / He has no right to tell a woman when and where to create one / So will the real men get up? / I know you’re fed up, ladies, but keep ya head up

If ever there was an anthem for women’s rights, this is it. Written long before Death Row Records, before the sexual assault case, the subsequent imprisonment and before all the drama and beef that more than likely contributed to his death.

Here, Tupac samples classics The Five Stairsteps’ ‘Ooh Child’ and Zapp’s ‘Be Alright’ to great effect. One of the first rappers to pay tribute to his mother and the women around him. ‘Keep Ya Head Up’ remains a poignant and essential 2pac song.

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