Returning to original material after the 2017 covers album Down Hearted Blues, Eilen Jewell is unusually engaged with the modern world on Gypsy. This doesn't mean the singer/songwriter is abandoning her Americana for country-pop. With its smoldering, swampy groove and sawing fiddles, the opening "Crawl" makes it clear that Jewell continues to mine and fuse all aspects of American roots music; she's as comfortable with country as she is soul. What gives Gypsy its contemporary kick is how Jewell stares directly at the political turmoil that's roiling America in the waning years of the 2010s. On "79 Cents (The Meow Song)," she takes aim at both the gender pay gap and Donald J. Trump, tying the two together on its closing refrain, while "Beat the Drum" -- another key cut that seems to arise out of the swamp -- is a rallying call to resist. As strong as these two songs are, what makes them so effective is how they're surrounded by songs of empathy, sensuality, and humor, songs that help convey a full range of human feeling; pleasure sits alongside protest, which is perhaps as sensible a way to live in 2019 as anything else. As impressive as these textured emotions are, Gypsy succeeds as a record because of Jewell's facility with roots music. When she sings a hardfloor honky tonk tune like "These Blues," she's as convincing as when she's working a steamy slow dance like "Witness," and her voice is as affecting when it's plaintive ("Fear") as when she's telling a sly joke ("You Cared Enough to Lie"), and that skill is what ties the disparate Gypsy together, making it sound fully realized and easy, which is a pretty alluring combination.
AllMusic Review by Stephen Thomas Erlewine