Whiskeytown had ceased to be a band in the truest sense by the time they recorded their third (and final) full-length album, Pneumonia; the group began to collapse during the touring following Strangers' Almanac, with members coming and going at a remarkable pace, and for the Pneumonia sessions, the only musicians on hand who had appeared on Faithless Street three years earlier were lead vocalist and songwriter Ryan Adams and violinist and backing vocalist Caitlin Cary. Multi-instrumentalist Mike Daly and percussionist/producer Ethan Johns dominated the sessions' sprawling cast of players, with James Iha and Tommy Stinson popping up on some tracks. Ultimately, Pneumonia sounds more like a Ryan Adams solo project than anything else, and it walks a decidedly different path than the Whiskeytown albums that preceded it -- there are no charging rockers in the manner of "Drank Like a River" or "Yesterday's News," and the country twang of "Too Drunk to Dream" or "Someone Remembers the Rose" has receded into the background (though Cary's violin and occasional mandolin or steel guitar lines from Daly do add a high-lonesome undertow to several songs, especially the plaintive "Sit and Listen to the Rain" and "My Hometown"). This is easily Whiskeytown's most ambitious and eclectic work, and the sparkling pop of "Don't Be Sad" and "Mirror Mirror," the lovely faux-tropicalia of "Paper Moon," the haunting tape-loop reverie of "What the Devil Wanted," and low-key power balladry of "Crazy About You" all prove that, despite his reckless public persona, Ryan Adams had gained a wealth of maturity and intelligence (at least as a songwriter and recording artist) since the last time he'd entered a recording studio. Pneumonia was recorded in 1999, but the closing of Outpost Records in the wake of that year's Polygram/ Universal merger put the album on the shelf for two years; in the meantime, Pneumonia developed an underground reputation as a lost classic, and while that description is going a bit far to make a point, it is an undeniably striking and beautifully crafted set of songs, and it's interesting to imagine where this music would have taken Whiskeytown if the album had met its original release date -- assuming that Whiskeytown was still a band by the time the record was finished.
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AllMusic Review by Mark Deming