Both icon and iconoclast, Sinead O’Connor has been making music, rejecting stereotypes and defying expectations for more than a quarter century. Her clean-shaven head, ferocity of intelligence and intent, dignified persona, and penetrating aesthetic acuity established a new template for women in popular culture. She obliterated objectification and demanded to be taken seriously as an artist.

In 1987, she released The Lion and The Cobra, and charted her first alternative hits “Mandinka,” “Troy,” and “I Want Your (Hands On Me).” Her 1990 sophomore follow-up, I Do Not Want What I Haven’t Got, peaked at #1 on the Billboard Top 200 while her Prince-penned single, “Nothing Compares 2 U,” reached #1 on the Hot 100 and earned her a Grammy for Best Alternative Music Performance. She would later withdraw her name from Grammy consideration despite multiple nominations in an act of protest.

Recorded as a tribute to her mother, who’d died half a decade earlier, O’Connor’s take on “Nothing Compares 2 U” was bleak but heartfelt, leaving listeners on both sides of the pond awestruck. “Nothing Compares 2 U” continues to hold a place in the hearts of many, still regularly turning up on lists as one of the greatest cover songs – or just greatest songs, period – of all time.

Her groundbreaking video for “Nothing Compares 2 U,” featuring Sinead’s unforgettable performance in single-shot close-up, took home the Best Video trophy at the 1990 MTV Video Music Awards, marking the first time a woman had won the Best Video category.