Sinead O'Connor ranked among the most distinctive and controversial pop music stars of the 1990s, the first and in many ways the most influential of the numerous female performers whose music dominated airwaves throughout the decade. Brash and outspoken, with her shaven head, angry visage and shapeless wardrobe a direct challenge to the popular culture's long-prevailing notions of femininity and sexuality, O'Connor irrevocably altered the image of women in rock; railing against long-standing stereotypes simply by asserting herself not as a sex object but as a serious artist, she kick-started a revolt which led the way for performers ranging from Liz Phair to Courtney Love to Alanis Morissette.

O'Connor was born in Dublin, Ireland on December 8, 1966. Her childhood was often traumatic: her parents divorced when she was eight, and she later claimed that her mother, who was killed in a 1985 automobile accident, frequently abused her. After being expelled from Catholic school, O'Connor was arrested for shoplifting and shuttled off to a reformatory; at the age of 15, while singing a cover of Barbra Streisand's "Evergreen" at a wedding, she was spotted by Paul Byrne, the drummer for the Irish band In Tua Nua (best known as proteges of U2). After co-writing the first In Tua Nua single, "Take My Hand," O'Connor left boarding school in order to focus on a career in music, and began performing in area coffeehouses; she later studied voice and piano at the Dublin College of Music, and supported herself delivering singing telegrams.

Upon signing a contract with Ensign Records in 1985, O'Connor relocated to London; the following year she made her recorded debut on the soundtrack of the film The Captive, appearing with U2 guitarist the Edge. After scrapping the initial tapes for her debut LP on the grounds that the production was too Celtic, she took the producer's seat herself and began re-recording the album, dubbed The Lion and the Cobra in reference to Psalm 91; the result was one of the most acclaimed debut records of 1987, with a pair of alternative radio hits in the singles "Mandinka" and "Troy." Almost from the outset of her career, however, O'Connor was a controversial media figure; in interviews following the LP's release, she defended the actions of the IRA, resulting in widespread criticism from many corners, and even burned bridges by attacking longtime supporters U2, whose music she declared "bombastic."

However, O'Connor remained a cult figure prior to the release of 1990's chart-topping I Do Not Want What I Haven't Got, a harrowing masterpiece sparked by the recent dissolution of her marriage to drummer John Reynolds. Boosted by the single and video "Nothing Compares 2 U," originally penned by Prince, the album established her as a major star, but again controversy followed as tabloids took aim at her romance with Black singer Hugh Harris while continuing to attack her outspoken politics. On American shores, O'Connor also became the target of derision for refusing to perform in New Jersey if "The Star Spangled Banner" was played prior to her appearance, a move which brought public criticism from no less than Frank Sinatra, who threatened to "kick her ass; " she also made headlines for pulling out of an appearance on the NBC program Saturday Night Live in response to the misogynist persona of guest host Andrew Dice Clay, and even withdrew her name from competition in the annual Grammy Awards despite four nominations. O'Connor also continued to confound expectations with her third album, 1992's Am I Not Your Girl? a collection of pop standards and torch songs which failed to live up to either the commercial or critical success of I Do Not Want What I Haven't Got. However, any discussion of the record's creative merits quickly became moot in the wake of her most controversial and damaging action yet: after finally appearing on Saturday Night Live, O'Connor ended her performance by ripping up a photo of Pope John Paul II, resulting in a wave of condmemnation unlike any she'd previously encountered. Two weeks after the SNL performance, she appeared at a Bob Dylan tribute concert at New York's Madison Square Garden, and was promptly booed off the stage.