Sinead O’Connor, a singer with religiosity in her voice, plays to true believers at City Winery Monday

By MARK GUARINO | Chicago Sun-Times

She is shy, she said, which is why she wore sunglasses. They stayed on for most of the night. When she took them off, we finally got to see her: The diminutive singer with the massive, emotive voice.

In playing City Winery Monday, the first of a three-night stand, Sinead O’Connor both looked in her element but sounded far outside it. Her five-member band, including her producer and ex-husband John Reynolds on drums, fit snugly on the small stage, and they filled the room generously. However, O’Connor’s voice presented complexities more suited to the rafters of the United Center. She wailed, she whispered, she blended into a three-part harmony. She sang alone with no accompaniment, she led her band at top volume.

For someone known to the masses as the defiant singer who ripped up the picture of the Pope on national television, O’Connor is a far more elusive as a singer. On “I Am Stretched On Your Grave,” (dedicated to Lou Reed), she stood alone on stage and exhibited the vocal phrasing of a master — moving the microphone close and then far away to deliver both fanfare and breathless whispers. Not one wine glass in this wine themed supper club clinked. Even the wait staff froze.

The 90-minute show leaned heavily on songs from “How About I Be Me (And You Be You)?” (One Little Indian), a recent album, that sounded perfectly aligned with her earliest music. The themes of spiritual longing, personal catharsis, malice towards either a lover or the Catholic Church, were all there, as were songs that could double as chapel hymns. “Thank You For Hearing Me” crested mightily despite its simple message of grace; she and two female members of her band joined her to sing a capella around a single microphone for “In This Heart,” a song that was very Irish, making its grief a beautiful thing.

Thanks to the popularity of reality television karaoke contests, and the advancement of pitch-altering technology, live singing is becoming a disappearing act. Last month in an interview, O’Connor told me that shows like “The X Factor” have “really done a lot of damage” to the emerging generation of singers, making them think that vocal bloviating and imitative flattery are more valued than internalizing what a song is all about and conveying it deeply from within.

“Really, these people are all about getting famous. They’re not going, ‘I really want to be a (expletive) singer.’ It’s all very strange,” she said.

Indeed, it would be hard to imagine a performer as unique as she getting the nod from “X Factor” producer Simon Cowell, of whom she recently told an Irish television host was a “murderer of music.”

O’Connor infused “The Last Day of Our Acquaintance” and “Emperor’s New Clothes” with fortitude, later turning to “Fire On Babylon,” a reggae tune, and Bob Dylan’s “Property of Jesus,” an appropriate fit. There was no mention of a certain Disney Channel star-turned-sex vixen, however O’Connor broke out a smile during “V.I.P.” when the crowd started chuckling when a lyric name-checked an old nemesis, the Pope.

Eventually, those sunglasses came off and O’Connor slipped into her comfort zone, encouraging people to dance, and thrashing herself on “Psalm 33,” the sole punk moment of the night.

“I have a universe inside me/Where I can go and spirit guides me,” she sang on “The Healing Room.” Those at City Winery Monday can attest those stars were aligned.