Photography: Price Harrison

Boo Ray & Lilly Winwood debut their collaborative track “Hard to Tell,” exclusively with C&I.

As part of his vinyl single collaboration series called “Boocoo Amigos,” Nashville country-rock singer-songwriter Boo Ray teamed up with Lilly Winwood, Americana singer and daughter of Rock & Roll Hall of Famer Steve Winwood.

After the success of their first collaboration — a rendition of the classic Kenny Rogers-Dolly Parton duet “Islands in the Stream” — Ray and Winwood joined forces again for their original A-side single called “Hard to Tell.”

“Lilly’s clever like a safe-cracker, cooler than a polar bear’s toenails, and has a wonderful uproarious laugh,” Ray says. “She’s a world-class vocalist and smart soulful songwriter. We were hangin’ and talking ’70s music — Linda Ronstadt, Gerry Rafferty, Eddie Rabbitt, and the Bee Gees — and went down the rabbit hole of the Grease soundtrack, came out the other side, and landed on ‘Islands in the Stream.’ We knew we just had to record ‘Islands’ and write an A-side to accompany it.”

“Hard to Tell,” is a fun, whimsical track that utilizes its steel guitar, organ, and bluesy guitar licks to emphasize Winwood’s unique voice and Ray’s signature eccentric style.

“‘Hard to Tell’ is one I’d been writin’ on for a female artist like Kacey Musgraves, Miranda Lambert, Cam, or Grace Potter. I’m empathetic of what the dating-scene dilemma is like these days for women, let alone smart women, and this song seemed to speak to that. I started it as an electric, drunken, honky-tonk waltz. Lilly immediately had the lyric fix it needed. We flipped the beat on it and put some Jordache jeans, ankle boots, and an old Muscle Shoals T-shirt on the song. I think it took about 20 minutes to write, and then we went honky-tonkin’,” Ray says.

Ray and Winwood wrote and recorded “Hard to Tell” to pair with the B-side “Islands in the Stream” on a 7-inch 45-RPM pressing by Kindercore Vinyl.

To listen to “Islands in the Stream,” click here.

Check out the exclusive premiere of “Hard to Tell” below.


For more information on Boo Ray and his upcoming shows, visit his website.

For more information on Lilly Winwood and her upcoming shows, visit her website.  

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