Rapper Tupac Shakur d!ed 27 years ago, after succumbing to injuries from a shooting that took place on a Las Vegas street nearly a week before. He was only 25 years old. He would have been 52 today.

Shakur’s controversial and influential career lasted just five years, but the world of rap music and the music industry at large still feels his impact two decades after his untimely d3ath.

From his first appearance with the rap group Digital Underground to starring roles in Hollywood movies and his final, blockbuster studio album, “All Eyez on Me,” Tupac shook up the culture and gained a massive following.

Here are the biggest moments of Tupac Shakur’s career leading up to his d3ath: 

After studying poetry, theater, and music in high school, Shakur got his first break when he became a road!e and backup dancer for the rap group Digital Underground in 1990. His first music credit came on a soundtrack single for the 1991 Chevy Chase-led film “Nothing But Trouble,” which he also appeared in.

In November 1991, Shakur released his debut solo album, “2Pacalypse Now,” on Interscope Records. The album was certified gold for sales of 500,000 or more copies — minuscule compared to the success of his later records — but his social commentary on songs like “Brenda’s Got a Baby” established him as an important voice in rap.

Interscope

Shakur had his first starring role in the 1992 New York City crime thriller “Juice,” acting alongside Omar Epps, Samuel L. Jackson, and Queen Latifah.

Paramount Pictures

In 1993, Shakur released his second album, “Strictly 4 My N—-Z,” and it was his major breakthrough as an artist. The LP went platinum and produced two major hits, “I Get Around” and “Keep Ya Head Up.”

Source: RIAA

Later that year, Shakur starred opposite Janet Jackson in the hit romantic drama “Poetic Justice.”

Columbia Pictures

After surviving being shot five times in 1994, Shakur was sentenced to serve four and a half years in prison for a s3xual assault charge in 1995. His third album, 1995’s “Me Against the World,” became the first No. 1 album released by an artist during a prison stint and went on to sell over 3 million copies.

Interscope

In October 1995, d3ath Row Records boss Suge Knight posted Shakur’s $1.4 million bail, and he was released from prison. Afterward, Shakur immediately began recording new music for an album under d3ath Row.

Shakur (L) and d3ath Row’s Suge Knight (R). AP Images

“All Eyez on Me,” Shakur’s 1996 double album for d3ath Row, would be the biggest release of his career — selling over 10 million copies to date — and the last before his d3ath. Leading up to its release, Shakur and East Coast rapper Notorious B.I.G. became embroiled in a rap conflict over opposing diss tracks.

On September 7, 1996, Shakur was sh0t four times while stopped at a red light in Suge Knight’s car in Las Vegas, Nevada. He d!ed six days later at the University Medical Center in Las Vegas, and his murd3r case remains unresolved.

Knight’s black BMW, which Shakur was sh0t in several days before this photo. Lennox McLendon/AP

From posthumous albums and a hologram appearance at Coachella in 2012, to his 2017 biopic, “All Eyez on Me,” Shakur’s legacy lives on, two decades after his untimely d3ath.

Demetrius Shipp Jr. as Shakur in “All Eyez on Me.” Open Road Films