While Shane MacGowan and Sinead O’Connor came onto the Irish music scene at around the same time, they didn’t have matching career trajectories. After leaving behind reform school and an abusive home life, O’Connor played in local pubs with a small group before being signed to produce her own albums. Her breakthrough came with “I Do Not Want What I Haven’t Got” in 1990. Meanwhile, MacGowan, who moved back and forth between Ireland and England growing up, was first noted for his poetry. His initial attempt to break into music fizzled in the late ’70s, but he found fame and fortune as part of the Pogues in the 1980s.
By 1994, MacGowan was out of the band he had co-founded, a consequence of drug and alcohol abuse that often overshadowed his work. But and O’Connor came together through a song MacGowan had originally written as part of the Pogues — a track for the film “Sid and Nancy” called “Haunted.” His cover with O’Connor, released as a single in 1995, was a hit for the pair, spawning a music video (above) and a sometimes-awkward promotional appearance on “Kenny Live” back in Ireland (via YouTube).
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But O’Connor came to have the same concerns about MacGowan’s substance abuse as his old bandmates had. According to the Irish Times, after she found MacGowan passed out from heroin at his London home in November 1999, she reported him to the police. He was arrested for possession.