Sinead O’Connor’s 10 Best Songs: Staff Picks

The music world lost one of the most singular voices — both in the vocal and artistic senses — of the past half-century this week with the death of Irish singer-songwriter Sinead O’Connor, at the age of 56. Equally adept at incendiary anti-government missives and heartbreaking torch songs, O’Connor never chased the pop mainstream, but was such a force of artistry that she ended up breaking through to it anyway.

In the U.S., O’Connor was best known for her tearjerking (and Billboard Hot 100-topping) rendition of the Prince-penned megaballad “Nothing Compares 2 U” — along with its impressionistic music video, a huge MTV smash that made her the first female winner for the Video Music Award for video of the year in 1990. As big a hit as “Compares” was, a series of uncommercial career decisions and controversial moments of protest (most notably her ripping up a picture of Pope John Paul II on a 1992 episode of Saturday Night Live) ensured that her time in the pop mainstream was relatively brief.

Nonetheless, O’Connor leaves behind an uncompromising catalog of brilliant moments, from Alternative Airplay hits like “Jump in the River” and “Success Has Made a Failure of Our Home” to deep cuts from her classic first two albums The Lion and the Cobra (1987) and I Do Not Want What I Haven’t Got (1990), to guest appearances on singles by The Edge and Massive Attack. O’Connor never stopped evolving musically, and never took the easy route with her talent, continuing to challenge herself and her fans decades into her career.

Below, Billboard staffers write about 10 of their favorite Sinead O’Connor songs, in chronological order: The protest anthems, the sensual come-ons, the inscrutable statements, and yes, “Nothing Compares 2 U.”