On 13th September 1996, Tupac Shakur died and he left behind a massive catalogue of songs that we have continued to enjoy to date.

In honour of his legacy, we are running through 15 of his best songs according to the Insyder team. The list was not easy to come by and it by no means discounts all the other songs not included. The other thing to note is that this list is not in any particular order, except alphabetical.

We will leave the exact ranking to you as your homework for today.

So let’s get down to it.

Brenda’s Got A Baby

This was a single from Tupac’s debut studio album 2Pacalypse Now released in 1991.

It features R&B singer Dave Hollister singing vocals in the background with Roniece Levias. It is about a 12-year-old girl named Brenda who lives in a ghetto and has a baby she can’t exactly support.

It peaked at number 7 on the Billboard Hot Rap Songs and number 23 on the Billboard Hot R&B/Hip-Hop Songs.

California Love ft. Dr. Dre

This was a single featuring Dr. Dre and Roger Troutman from the album All Eyez on Me. It was dropped as his comeback single after his release from prison in 1995 and it was his first single as the newest artist of Death Row Records.

It is one of Tupac’s most popular singles as well as his most successful.

It topped the Billboard Hot 100 for two weeks and was later the reason why Tupac was posthumously nominated for a Grammy Award under Best Rap Solo Performance and Best Rap Performance by a Duo or Group (with Dr. Dre and Roger Troutman) categories in 1997.


This was single featuring Talent from the album Greatest Hits which was a posthumous album released in November 1998. The song touches on the war on drugs, racism, police brutality, poverty and gang violence.

It was nominated for Best Rap Solo Performance at the Grammy Awards of 2000 and is still the only posthumous song to be nominated in this category. The song was also nominated at the MTV Video Music Awards for Best Editing in a Video & Best Rap Video in 1999.

Dear Mama

This was a single from the 1995 album, Me Against the World. 

The song is a tribute to Tupac’s late mother Afeni Shakur. It touched on the poverty he underwent as a child as well as his mother’s addiction to crack cocaine. In the song, Tupac argues that his love and deep respect for his mother supersedes the bad experiences of his childhood.

The song peaked at number 1 on the Billboard Hot Rap Singles chart for five weeks and peaked at number nine on the Billboard Hot 100.

Hail Mary

This was a single from Tupac’s final album The Don Killuminati: The 7 Day Theory, under his new stage name, Makaveli. It was released posthumously and is one of the rapper’s most popular hits. The song features Tupac’s thoughts about the violence and negativity surrounding him, his prayers, and some biblical references.

The song peaked at number 8 on the Billboard Hot Singles chart.

Hit ‘Em Up

This was a diss track by Tupac featuring the Outlawz.

It features ferocious insults to several East Coast rappers, chief among them, Shakur’s former-friend-turned-rival, Notorious B.I.G., also known as Biggie Smalls. Though considered to be one the best diss tracks ever recorded, it is filled with controversy since Tupac’s murder in a drive-by-shooting happened just three months after its release.

The release of this song is widely regarded as the beginning of the East Coast-West Coast war and a symbol of what became the most poisonous battle in the history of hip hop.

Holla If Ya Hear Me

This was a first single released from Tupac’s second solo album, Strictly 4 My N.I.G.G.A.Z.

It samples “Do It Any Way You Wanna” by People’s Choice and Public Enemy’s “Rebel Without a Pause”. It was a reflection of Tupac’s frustrations with black poverty, police injustice, and his perceived persecution from political figure Dan Quayle.

The song was featured in the 1994 film Above The Rim, which starred Tupac.

If I Die 2nite

This was a single from the 1995 album, Me Against the World.

It samples Betty Wright’s “Tonight Is the Night” and Alicia Myers’s “If You Play Your Cards Right”.

Keep Ya Head Up

This was a single from Tupac’s 1993 album Strictly 4 My N.I.G.G.A.Z. It later appeared in his posthumous 1998 Greatest Hits album.

The song features Dave Hollister and is dedicated to black women and particularly, Latasha Harlins, in reference to the 1992 L.A. riots. The beat is sampled from Zapp’s “Be Alright” and the chorus is from The Five Stairsteps’ “O-o-h Child”.

The song peaked at number 12 on the Billboard Hot 100, number 7 on the Hot R&B/Hip Hop Single and number 2 on the Hot Rap Songs.

It was featured in the Tupac Biopic All Eyez On Me.

Life Goes On

This was a single from Tupac’s 1996 album, All Eyez On Me.

The song is about the streets snatching people’s lives, and how even though you lose someone, you can’t time off to mourn because that’s not what the victim would want you to do – they would want you to move on with your life because they’re not coming back.

Me Against The World

This was a single from the similarly titled 1995 album, Me Against the World. It features Dramacydal.

Only God Can Judge Me

This was single from Tupac’s 1996 album, All Eyez On Me. It was sampled of “Tonight” by Kleeer.

To Live And Die In LA

This was the second single from the last album that Tupac worked on during his lifetime, The Don Killuminati: The 7 Day Theory. The song is a beautiful and timeless ode to the rapper’s city, LA.

Until The End Of Time

This was a single from the posthumous album by the same name.

The song features R.L.Huggar from the R&B group Next and was a huge contributor to the album going 4x platinum.

It features a sample of Mr. Mister’s popular 1985 #1 song “Broken Wings” and was even initially titled “Broken Wings” before legal issues came up.

2 Of Amerikaz Most Wanted ft. Snoop Dogg

This was a single from Tupac’s 1996 album, All Eyez On Me and features Snoop Dogg. It was released as promotional single and was the album’s second after “California Love”.

The song peaked at number 46 on the US Billboard Hot R&B/Hip-Hop Airplay chart. It was played on 2Pac’s biopic, All Eyez On Me (2017), with 2Pac and Snoop in the studio recording the song.

The video was directed by Tupac’s production partner, Gobi M. Rahimi and was filmed four months before the September 1996 shooting.