How Was Tomorrow is essentially the American-release version of the Cash Brothers' debut Raceway, which had hit record shelves in their native Canada two years earlier. The song lineup is slightly altered. It deletes four songs from Raceway and replaces them with three new tracks, among them the hushed, highly atmospheric gem "I Am Waiting." The album is, indeed, better than a great majority of the so-called alt-country and No Depression efforts that glutted the music industry in the 1990s, this side of Jayhawks and Wilco. In fact, the songs have all the best aspects of the music of Neil Young and Gram Parsons, the most oft-cited but rarely matched country-folk luminaries, while slyly referencing the folkiest side of Bruce Springsteen ("Nebraska") as well. And the duo easily equals the harmonies of Mark Olson and Gary Louris, occasionally even approaching the sweet tandem singing of the Everly Brothers ("Take a Little Time"). The hooks are consistently so gorgeous that you immediately want to wrap yourself in them, despite the sparseness of the music and mood. It is a bucolic, beautifully melancholy, and humble album, even when it turns up the amplifiers, and it deserves to win the brothers a lot of American converts.
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AllMusic Review by Stanton Swihart