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Finding even better days

Gypsy Tailwind show power and Grace
By SAM PFEIFLE  |  June 17, 2009

gypsy main
A CRISP PACKAGE: Gypsy Tailwind offer a taste of what is to come. 
Photo by Matthew Robbins

Gypsy Tailwind have been a slow build. Though Halo Sessions was one of the best local albums of 2008, it seems no one really heard it until 2009, thanks largely to the radio success of "So Lonely," a single whose melancholy bounce was heartbreakingly honest: "I'll tell you a secret: I drank myself to sleep last night." Their shows, too, have been measured out to increase anticipation and capitalize on opportunity. No one who wound their way down Market Street to the Big Easy after Ray LaMontagne's Merrill Auditorium show was disappointed with Gypsy's similar combination of roots and soul.

And they're just getting started, really. Halo Sessions' spare and measured arrangements were in some ways simply sketches by two vocalists, Dan Connor and Anna Lombard, who were trying to figure out just what kind of art they could make together. Over the past year they've collected a band to fill things out: Max Cantlin (This Way) on guitar, Tyler Stanley (Sly-Chi) on keys, Colin Winsor (Jaye Drew and a Moving Train, Jason Spooner) on bass, Chris Dow (Band Beyond Description) on drums.

Then they re-entered the studio with Jonathan Wyman and produced Grace, released last week and celebrated with a show this Saturday at the Port City Music Hall. It is bigger and bolder and more true to their stage presence, akin to a modern-day Fleetwood Mac, if they'd been formed in Nashville instead of London, raised on Dylan and Emmylou Harris instead of John Spencer and Howlin' Wolf.

If you've spent 100 listens with Halo, Grace will require something of a recalibration, however. From the get-go, "Way to Here" opens with soaring minor-key strings (a four-piece section of Anna Maria Amoroso, Heather Kahill, Julie Anderson, and Tim Garrett), and though Connor's voice is as velvet smooth as ever, when the full band enters it does so with a confidence of belonging. In fact, while Connor and Lombard trade verses, creating a narrative dynamic like you're eavesdropping on an intimate conversation ("I'm going to grab the things I own and move away"; "With all my love I wish you were still here"), there are times where they aren't the most important thing happening, and the finish is a 30-second playout of active cello and trilling strings that wholly ignores them.

Remember Ray LaMontagne's maturation with producer Ethan Johns? The difference between Old Crow Medicine Show with Don Was? This progression is similar.

And they're getting it out of the way in a hurry. The new album's second track, "The Letter," opens with a horn section (Rustic's Ryan Zoidis and Dave Noyes, naturally, along with Mark Tipton, Joe Parra, and John Maclaine), for a song that's all lonesome-heart Lombard: "So here's your letter/I'm gonna sing it cuz it's my way." She's definitely more aggressive throughout the album, at times projecting major volume. She goes toe to toe with Cantlin's throaty electric guitar in "Silver and Gold" without a petal wilted (and listen there for Bob Hamilton's banjo — a great melancholy foil).

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  Topics: CD Reviews , Entertainment, Music, Grant Street Orchestra,  More more >
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