Out of hundreds of concerts I covered in 1999, here are my favorites:
1. Caetano Veloso at Ravinia, July 13: Remarkably, this legendary singer-songwriter — whose innovations in the Tropicalia movement were regarded as so subversive that the Brazilian government expelled him for two years in the early ’70s — had never played Chicago before. That changed last summer, and Veloso did not disappoint. He both embraced the stereotype of the suave bossa-nova singer and subverted it, blending native drum rhythms with Gil Evans-style horn charts and lilting folk ballads with aggressive techno experiments.
2. Tom Waits at Chicago Theatre, Aug. 26: Another rare appearance — the first in more than a decade — by the last great saloon singer. With his floppy hat and undertaker’s clothes, Waits stomped like a mule and rasped like “Satchmo” Armstrong with his guard down. He says he’s got only two types of tunes — grim reapers and grand weepers — but with his flair for the theatrical (flashlight, glitter, sawdust), he made the variations seem endless.
3. Bruce Springsteen at United Center, Aug 27: Springsteen didn’t use his reunion with the E Street Band as an excuse to indulge in nostalgia. Instead, he ignored many of his top-10 hits to explore some of the deepest crevices of his massive songbook, which made this that rare superstar arena tour that didn’t play like a greatest-hits take-the-money-and-run routine. And who could forget the moment near the end of the show when the band assembled around a microphone to deliver “If I Should Fall Behind,” a hymn-like statement about the endurance of friendship?
4. Plastic People of the Universe at the Empty Bottle, March 5: As true political-rock rebels, this Czech band walks the walk. Some band members ended up in jail for defying the Communist dictatorship in the ’70s, and their shattering music — the Velvet Underground meets Ornette Coleman — bears witness to their protest.
5. Cafe Tacuba at House of Blues, Nov. 17: One of the best rock bands of the ’90s tramples barriers of language, tradition and genre with a brazen blend of street-level busking, studio experimentation and rock-star charisma (courtesy of singer Anonimo, who resembles a wiry, postpunk Rasputin). Mixing traditional acoustic instruments with drum machines, clattering percussion with jazzy upright bass lines, Tacuba creates a river of music that connects huapango to Brian Eno and Tejano to techno.
6. Lauryn Hill at Chicago Theatre, Feb. 20: If there were any doubts about Hill’s ability to go it alone without her Fugees bandmates, they were answered on this night. Explicitly reconnecting hip-hop to its roots in reggae and gospel, Hill sang, rapped and testified about one woman’s quest for self-empowerment — and raised the standard for all hip-hop tours to follow.
7. Brian Wilson at the Rosemont Theatre, March 10: The troubled genius was almost like a spectator at his own coming-out party. Yet it was profoundly moving to watch as Wilson stood and listened, a lonely silhouette enveloped in the safety net of a superb band that played his beautiful but rarely performed instrumental pieces from “Pet Sounds.” Nearly as reclusive as his idol, Phil Spector, Wilson began the night shakily, but eventually began to enjoy his moment thanks to the adoration of the audience and the healing power of his music.
8. Iggy Pop at Metro, Oct. 28: He still embodies the rock ‘n’ roll Id run amok better than any performer — even at 52 the concept of aging gracefully seems never to have occurred to him. He slumped to his knees, barechested with an acoustic guitar, hair falling down his back like a noble savage, to sing perverse folk songs about a lifestyle that is part comic book, part pulp-fiction nightmare. Then he rose and roared the 30-year-old trailer-park anthems that Kid Rock and Fred Durst can only mimic, leaving toppled speaker cabinets, smashed microphones and welts the size of Wrigleyville in his wake.
9. John Prine at Chicago Folk Center, Nov. 19: He still delivers like the Maywood mailman he once was — the impish smile, the croak of a voice, the devastating details tucked inside the gently self-mocking narratives. Only this time, there is an air of celebration: Prine had beat cancer, and though his voice is even scratchier than usual, he has help from a few friends — his band, the pristine-voiced Iris DeMent and an audience that embraces him like a favorite uncle.
10. Hole at the New World Music Theatre, May 22: She may have gone Hollywood, but on stage Courtney Love still plays the wayward, ultra-vulnerable rock-star role better than any of her contemporaries. Whether paying tribute to the late Jim Ellison or wading into the audience in search of trouble, taunting the frat boys in the audience or catering to them by flipping off her top, La Love was a tangle of contradictions, as perversely watchable as a 10-car expressway pile-up.
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Hear Greg Kot on “Sound Opinions” at 10 p.m. every Tuesday on WXRT (93.1 FM)
