Tupac Shakur’s 10 greatest songs of all time
Born Lesane Parish Crooks, Tupac Amaru Shakur was more than just a rapper, actor, model, or entrepreneur; he was a transformative figure in music, poetry, and street culture. Tupac was the pioneering gangster rapper who brought depth and message to his work, coupled with the emotional insight that his impact would be fleeting.
Shrouded in mystique after his untimely death in 1996, Tupac Shakur became an emblem of his generation, blending societal insights with hard-hitting lyrics. Above all, 2Pac was a remarkable artist.
To honor his legacy, we’ve compiled a list of his ten most essential tracks from his extensive and diverse discography. This selection includes songs from both before and after his passing, underscoring that Tupac’s influence endures.
Tupac’s unique ability to be both vulnerable and resilient, to simultaneously deliver powerful punches and reveal his own wounds, is evident in these tracks. They capture the duality, imperfections, and humanity of an artist whose impact remains profound.
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.”
In the opening moments, Tupac gives voice to a generation of fatherless children, questioning how one can grow into manhood without a role model. Over a sample of ‘Soul Shadows’ by The Crusaders featuring Bill Withers, Tupac and his stepbrother Mopreme channel their frustrations about the absence of a steady father figure and the challenges faced by single mothers in the Black community.
Mopreme’s verse highlights the impact of this absence, rapping, “Moms had to entertain many men / Didn’t want to do it but had to pay the rent again / I’m getting older, starting to be a nuisance / Moms can’t stand me ’cause I resemble my father.” This track powerfully addresses the profound effects of a missing father on the family dynamic.
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.“
In the final years of his life, Tupac became increasingly distrustful of those around him, suspecting that his former friends Biggie and Puffy were involved in setting him up. Despite repeated denials from Bad Boy Entertainment, tensions flared when, while Tupac was in prison facing charges related to a sexual assault and recovering from five recent gunshot wounds from a robbery at a New York recording studio, The Notorious B.I.G. released a track titled ‘Who Shot Ya?’
The timing was certainly unfortunate. After Tupac was released on bail, funded by his contract with Death Row Records, he targeted Bad Boy in his music, sometimes subtly and other times explicitly.
‘So Many Tears’ from the album Me Against the World showcases a more introspective and somber side of Tupac. Released in 1995, this album reflects his struggle with paranoia and the aftermath of the Quad Recording Studio shooting. Despite his incarceration at the time, the album debuted at number one, surpassing 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 standout single from Me Against the World features Tupac honoring his mother, Afeni Shakur, a former Black Panther and recovering addict. Sampling Joe Sample’s ‘In All My Wildest Dreams,’ Tupac delivers a poignant performance, blending raw, sorrowful emotion with a tenderness rarely seen in rap.
This track offers a profound introduction to Tupac’s artistry.
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.“
With a subtly altered sample from James Brown’s “The Spank,” “Trapped” opens with a powerful narrative about the struggles of black men facing police brutality. This track, the debut single from Tupac’s first album, features Digital Underground’s Shock G on backing vocals and showcases a stylized 2Pac logo resembling a handgun.
Following the video’s release, Tupac experienced a brutal encounter with Oakland police officers, who assaulted him after a jaywalking stop. The injuries from this incident left lasting marks 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 after Tupac’s death, “Changes” includes vocals from “I Wonder If Heaven Got a Ghetto” and remains one of his most cited songs. The track delivers sharp critiques of law enforcement and government, reflecting on the murder of Black Panther co-founder Huey P. Newton and describing the harsh realities faced by underprivileged black youth in America.
2Pac channels his anger and disillusionment over the lack of progress and support in his community. The song’s final lines ominously foreshadow his tragic end: “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 securing his bail with a handwritten three-page contract while incarcerated, Tupac Shakur set out to prove his value to Death Row Records’ new CEO, Suge Knight. Collaborating with Dr. Dre, who also produced this track and the hit “Can’t C Me,” Tupac made a remarkable comeback to the mainstream. “California Love,” in its various versions, still feels as vibrant today as it did in 1995. Shake it up, 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.”
Where to begin? This might be the most intense track from Tupac, unleashing a fierce attack on several East Coast rappers, with the primary focus on Bad Boy Records’ The Notorious B.I.G and Puff Daddy. Tupac accused them of being involved in the Quad Studios robbery and shooting, an incident that took place while Puff and Biggie were in the studio.
The song opens with Tupac boasting about an alleged affair with Biggie’s estranged wife, Faith Evans, and then proceeds to dismantle the label and its affiliates. The Outlawz joined Tupac in delivering a barrage of verbal attacks against his rivals. The music video, featuring caricatures of Puff, Biggie, and Lil’ Kim, mirrored the song’s raw aggression.
Adding to the confrontation, the Johnny J-produced track samples Junior M.A.F.I.A.’s “Get Money,” renaming it “Take Money,” and reportedly includes vocals from Faith Evans. The song sparked significant controversy, with Public Enemy’s Chuck D. later commenting that Tupac had crossed a line with this track.
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 simplistic to label Tupac Shakur merely as a Gangsta Rapper, even though he excelled in that role for a time. Beyond that, he was also a poet, actor, and activist, revealing a vulnerable and compassionate side that few rappers have showcased.
In “Letter to My Unborn,” which samples Michael Jackson’s “Liberian Girl,” Tupac delivers a deeply personal and touching message to his unborn child. The track reflects on his tumultuous life, confronts the reality of death, and warns his future offspring about the challenges they may face. Released posthumously in 2001, this song stands out as one of the more impactful releases following his death.
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 the iconic Nate Dogg, “How Long Will They Mourn Me” stands out as a key track on Thug Life’s sole studio album. Created shortly after the passing of Tupac’s friend Kato, the song serves as a tribute with contributions from the rest of Thug Life.
In September 2019, to mark the album’s 25th anniversary, a re-released version of the track appeared with alternative lyrics. While it mirrors the original in its musical arrangement, the revamped version lacks the same emotional impact and lyrical resonance as the original.
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 there was ever a definitive anthem for women’s rights, this is it. Created well before his time with Death Row Records, before the sexual assault case, and before the ensuing conflicts that likely contributed to his untimely death, Tupac’s track stands as a powerful statement.
In this song, Tupac skillfully samples classics such as The Five Stairsteps’ “Ooh Child” and Zapp’s “Be Alright.” It was among the first of his works to honor his mother and the women in his life. “Keep Ya Head Up” remains a deeply impactful and essential piece of Tupac’s legacy.
Credit Photo: “Retrato Tupac Shakur” by jlmaral is licensed under CC BY-NC-ND 2.0.
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