With new, up-and-coming artists questioning the importance of major labels to career development, it's worth studying the advantages and disadvantages faced by Ani DiFranco and Jeffrey Gaines, singer-songwriters whose careers are headed in vastly different directions. In 1992, the little-known Gaines released a self-titled collection of warm, melancholy message songs that doubled as little self-help manuals, powered by the singer's smoky, distinctive baritone and unmistakable sincerity. The album disappeared without much notice, but it developed a small, rabid fan base, with a B-side (a live cover of Peter Gabriel's "In Your Eyes") even scoring a bit of radio airplay. From there, however, everything went wrong. Somewhat Slightly Dazed, driven by a poppier sound, fizzled after a few great tracks, and the album flopped badly. Dropped from his label, Gaines resurfaced on a major indie, which did nothing with 1998's so-so Galore. Now on his third label, he finds himself looking to win back fans by returning to a form that both sold squat and made him known primarily for covering the music of Gabriel, with whom "In Your Eyes" will forever be associated no matter how big Gaines gets. The desperation of his situation hangs heavy over the new Always Be, which features two re-recorded versions of "In Your Eyes," tacks on a reworked version of 1992's "Hero In Me," and traffics heavily in the dusky inspirational ballads that pervaded his debut. The results intermittently work the old magic—Gaines remains a charismatic singer who has long deserved a wider audience—but it begs the question: What if "In Your Eyes" (the single, natch) does well? He'll be right back on the commercial path that led him to this desperate point, and that's a shame. Conversely, it's no secret that Ani DiFranco wrote the rulebook for building a successful career without compromise or corporate meddling. Self-releasing more than a dozen albums without the benefit (or detriment) of a label machine, she's become a superstar live draw and, ironically, label mogul who's as widely admired for her business savvy as for her instantly recognizable, influential folk music. DiFranco's willingness to stretch out creatively, expanding her once-barren arrangements into jazzy and/or pop-friendly directions, has been reviled in a few strident circles. But that just places her in yet another enviable place, making her apparent concessions to commercialism seem like anything but concessions: She's alienating fans, which constitutes some sort of risk, right? At this point, DiFranco can't lose. In that spirit, she's just released an ambitious two-disc studio collection, Revelling/Reckoning, which defies criticism by exploding in a dozen creative directions at once. DiFranco's defining characteristic has always been that she can't be reined in, and self-indulgence is often the price of undiluted independence, but it's hard to deny the pleasures sprinkled throughout the album's two-hour running time. Lavishly packaged and bearing an odd visual resemblance to Nine Inch Nails' Broken EP, Revelling/Reckoning represents DiFranco at her best and worst. The album finds ample room for gripping folk music ("Garden Of Simple," the mesmerizing "School Night"), an interminable lite-jazz instrumental ("Beautiful Night"), and slack funk ("Ain't That The Way"), the only rule of thumb being that the album is at its best when it aspires to make a personal connection. About two-thirds of the way through the superior second disc, DiFranco teases, "How sick of me must you be by now?," an apparent reference to the album's length and outsized ambition. The fact that she can make fun of herself for making the records she wants to make illustrates just how sweet artistic freedom can be. Here's hoping Gaines one day gets to revel in the same freedom.