The year 2016 was very unkind to many, as social media and the year’s news headlines will tell you. However, 2016 will also go down in infamy for being the year in which the world lost some of the most iconic and influential people in pop culture history. In no particular order, we’ve listed the five most culturally significant deaths this past year.

5. Muhammad Ali

“I hated every minute of training, but I said, Don’t quit. Suffer now and live the rest of your life as a champion.”

Muhammad Ali (also known as Cassius Clay) was one of the most important professional athletes to ever compete, but he was also a diligent worker and and passionate advocate for racial equality and religious peace.

To the United States and much of the world, Ali was a definitive symbol of ambition, diligence and personal expression — three qualities that continue to be significant to this day.

Muhammad Ali died of septic shock on June 3, 2016 at the age of 74.

4. Prince

“Despite everything, no one can dictate who you are to other people.”

As one of the most innovative musicians of the 20th century, Prince was a symbol of love, peace, and musical expression.

Prince is perhaps best known for his many pop-rock hits of the 1980s, such as “When Doves Cry” (1984), “Raspberry Beret” (1985), “Little Red Corvette” (1983), and, of course, “Purple Rain” (1985), but his musical career actually spanned three decades — the 1980s, 1990s, and the 2000s.

Prince left his mark on the United States and many other parts of the world through his voracious passion for music, his unique personality and his messages of love and peace.

Prince died on April 21, 2016 of an accidental overdose of pain medication. He was 57 years old.

3. Carrie Fisher

“Sometimes you can only find Heaven by slowly backing away from Hell.”

Carrie Fisher‘s performance of Princess Leia in the famous space-opera series Star Wars made her an instant pop culture icon and a symbol of beauty and intelligence. However, her troubled personal life and her journey to overcome her demons made her a symbol of persistence and empathy.

Fisher was diagnosed with bipolar disorder and admitted that she “self-medicated” with alcohol, prescription medications and cocaine.

After the orignal Star Wars trilogy, Fisher continued a successful acting career for more than 30 years. Her final performances in the latest additions to the Star Wars franchise are sure to add to her legacy.

Carrie Fisher died from complications following cardiac arrest on December 27, 2016. She was 60 years old.

2. David Bowie

“The truth is of course is that there is no journey. We are arriving and departing all at the same time.”

David Bowie, known for his musical gifts and electrifying personality, symbolized spiritual and personal expression and top-notch entertainment.

Bowie’s musical career spanned five decades and was characterized by hits like “Space Oddity” (1969), “Changes” (1971), “Rebel, Rebel” (1974), and “Ashes to Ashes” (1980).

Bowie was incredibly influential to people experiencing personal struggles with their identity. As his alter ego Ziggy Stardust, Bowie brought public discussion of sexual orientation into the mainstream, raising awareness of sexual identity and the struggles faced by LGBTQ individuals.

Bowie died of liver cancer on January 10, 2016 at the age of 69.

1. Fidel Castro

“Revolution is not a bed of roses. Revolution is a battle between the future and the past.”

Although not an entertainer like the rest of the people on this list, Fidel Castro‘s death is still one of the most culturally significant of 2016.

Castro served as the 17th “president” of Cuba from 1976 to 2008. Under his administration, Cuba became a socialist state; industry and business were made nationally public, and many state socialist reforms were implemented in the country.

Earlier in his life, Castro was a member of the Cuban rebellion to overthrow the right-wing military junta of Fulgencio Batista. The rebellion was eventually successful and led to Castro taking power over Cuba.

Castro was culturally significant in that he was a symbol of socialism, a label that was — and still is — unfriendly to many American citizens. However, Castro was also a symbol of social equality and national pride, an ideology that grows more and more popular as the 21st century rolls on.

Fidel Castro died on November 25, 2016 at the age of 90, but no cause of death was disclosed.