Eight essential Tupac tracks, from California Love to Ambitionz Az A Ridah

In a life that didn’t stretch past 25 years, Tupac Shakur changed the face of hip hop, helping to transform it from a emerging subculture to the global force we know it as today.

He was a fierce, battling MC, a master lyricist and a voice for social change - often all within the space of one song.

As we celebrate what would have been his 49th birthday, on June 16, we’ve rounded up the tracks you need to understand the man and the legacy.

How Long Will They Mourn Me

Released: September 26, 1994
Producers: Warren G, Professor Jay

Tupac was always acutely aware of mortality, both his own and of others around him. Released as part of his Thug Life group and later featuring on his Greatest Hits album, Tupac only has one verse on the song, but it wholly captures the confliction of mourning. In one line he’s swearing murderous revenge on the people who killed his friend and in the next he’s wondering whether he’ll ever get to heaven. Looking back now, the hook - “how long will they mourn me?” - is hauntingly prescient. He has been immortalised by his work now, but this verse was a snapshot of a man whose very future was in question.

California Love

Released: December 3, 1995
Producer: Dr Dre

It’s probably Tupac’s best known song and certainly one of his most radio-friendly, but California Love is still one of his greatest tracks. It’s an ode to Tupac’s home state and the life of carefree opulence it allows him to lead, with a Dr Dre beat that encapsulates the swagger and style of the West Coast scene. The internal strife that would colour so much of Tupac’s writing couldn’t be further out of mind than it was here. One of the defining tracks of the era.

Ambitionz Az A Ridah

Released: February 13, 1996
Producer: Daz Dillinger

Bold, brash and doused with nervous energy, Ambitionz Az A Ridah was the first song Tupac recorded after returning from his time in prison in 1995. It’s a statement of intent, a warning to others that he is back (“reincarnated”, as he puts it) and that he is untouchable. The spooky, sparse piano beat allows the unerring rhythm in his flow to come to the fore, almost spluttering but never unfocused. The song isn’t without its flashes of paranoia - “Pay off the block, evade the cops ‘cause I know they comin’ for me” - but even so this is Pac proving the he was back and there to stay.

All Eyez On Me

Released: February 13, 1996
Producer: Johnny “J”

The title track off his groundbreaking double album, All Eyez On Me is a dauntless acknowledgement of his place in the public gaze. It exemplifies his knowledge that he is rightfully at the top of the game, and his anger that anyone - whether that be his rap contemporaries, the police or the mainstream media - would even think of questioning it. And to top it all off, it’s all set against a smirking, laid-back G-funk beat.

Hit 'em Up

Released: June 4, 1996
Producer: Johnny “J”

There is a barely a line in Hit Em Up, one of the greatest diss tracks ever recorded, that isn’t laced with venom. With the acerbic rap beef between the East and West Coasts approaching its deadly pinnacle, Tupac dropped this track, firing shots at a number of East Coast MCs - chiefly at Notorious B.I.G. The very first line sets the tone (“First off, f*** your b**** and the clique you claim") and it barely lets up from there. A little over three months later, Tupac had been murdered.

To Live And Die in LA

Released: January 31, 1997
Producer: QD III

One of the last tracks he would record in his lifetime, To Live And Die in LA finds Tupac in a peaceful, warmly melancholic mood. It isn’t without its anger - it opens with a recording of a worried woman expressing her concerns over the simmering feud - but the beat that launches immediately after is the luscious G-funk relaxation. It’s another of the songs that sounds like retrospective and, knowing what we do now, eerily like a premonition.

Brenda’s Got a Baby

Released: October 20, 1991
Producers: Big D, The Underground Railroad

Tupac’s debut single set a precedent for the rest of his career. It’s an unflinching social commentary, a clear-eyed reflection of the world he saw around him, focusing on a teen pregnancy and the strife this would lead to. It also introduced Tupac as the conceptual rapper, with him presenting the song as if he was addressing a crowd.

Hail Mary

Released: March 7, 1997
Producer: Hurt-M-Badd

Deeply religious and reflective, Hail Mary is one of Tupac’s most disquieting posthumous singles. It shows how the conflict he struggled with throughout his life, between the violence that enveloped him and his need to find a way out of it all, would consume him until his final days. Listening now, to the beat with its dimly lit space and chiming funeral bells, it almost seems as if Tupac is speaking to us from directly from the grave.