Pretty Little Stranger is Joan Osborne's Vanguard Records debut; it is also her country and Americana record. She's cut soul and R&B, sung with Stevie Wonder, the Funk Brothers, the Grateful Dead, and Phil Lesh & Friends, fronted the Holmes Brothers (and produced their finest record to date), had one of the hugest hits of the '90s (that has been a millstone around her neck ever since), and dug into just about every area of American music. Given its steady high-profile popularity in early-2000s consciousness, country music seems like a logical next step. Pretty Little Stranger was produced by veteran and Grammy winner Steve Buckingham and the track selection is terrific. Osborne wrote six of the album's songs, and she covers Kris Kristofferson's "Please Don't Tell Me How the Story Ends," Jerry Garcia & Robert Hunter's "Brokedown Palace," Patty Griffin's "What You Are," Beth Nielsen Chapman's & Harlan Howard's "Time Won't Tell," the Red Lane & Larry Henley number "'Til I Get It Right," and Rodney Crowell's "When the Blue Hour Comes" (co-written with Roy Orbison and Will Jennings; Crowell guests on the track as a harmony vocalist). Other guests include Sonny Landreth, Alison Krauss, and Vince Gill. Those are the particulars.
The laid-back approach Osborne takes on this set is radical -- even a shock to the system. With that big, ringing, soulful, bluesy voice, she's chosen understatement in the face of the great trend in modern country toward female singers who express themselves in a big way -- check Jennifer Nettles of Sugarland, Karen Fairchild of Little Big Town, Gretchen Wilson, and Danielle Peck, to name a few. Osborne's instrument is a natural for the music -- in theory at least. The record is not tailor-made for the CMT or GAC channels, perhaps, or even country radio for that matter, but it sounds like there is another theory at work here. Osborne is showcasing her own songs on this record. Just as the late Lowell George's Thanks I'll Eat It Here was a singer's record, Osborne's Pretty Little Stranger is a songwriter's record. It's true that she may be too subtle in her approach on songs like the Griffin, Crowell, and Chapman/Howard cuts. She does a fine job of re-reading the Garcia-Hunter number because "Brokedown Palace" should have been a "real" country song in the first place. Her version of Kristofferson's classic "Please Don't Tell Me How the Story Ends" has little of Brenda Lee's drama or Rita Coolidge's deadpan grace, but what it does possess is the matter-of-fact hangdog directness that the songwriter intended.
While it remains to be seen what Nashville will do with Osborne's record, it hardly matters. The production techniques used by Buckingham are made for posterity; in ten years, Pretty Little Stranger will sound as contemporary as it does in 2021. Osborne's less aggressive approach suits the material very well, even if there is less distinction between some of the songs than there has been on her previous recordings. There is one number that does dig into the singer/songwriter's garden of roots and branches, and that's the slippery "Who Divided." Its electric piano, backbeat strolling guitar, and big snare underscore Osborne's funky, soul strutting voice. Even if the refrain is closer to contemporary Nashville, the tune itself is gritty; bluesed-out and utterly real. She swings and swaggers in all the right places. When the Hammond B-3 kicks in, it's easy to hear Osborne's R&B roots shining through in the sultry darkness and the brokenness in the grain of her voice. This is the voice of want, pain and thwarted desire. She follows it up with the glorious "Holy Waters," a pure country song that brings her into the terrain of true greatness as a gifted songwriter. Ultimately, Pretty Little Stranger is very good indeed; it is still not the record this gifted vocalist and songwriter could make, but it's solid, bittersweet, and crafty. It's a winner that keeps its best secret for last: that most of the best songs on this little platter are Osborne's.