Country Jukebox Jury LP: Hailey Whitters – The Dream (Deluxe Edition)

Six artists informed the writing and promotion of Hailey’s debut album, which is repackaged with five extra tracks featuring those six acts. Happy People was written with Lori McKenna and, before its appearance on the album, was given to Little Big Town, which was a nice little earner for Hailey and helped to fund the project, which came out in March 2020 just as you-know-what decimated artists’ careers.

Brent Cobb and Jordan Davis had Hailey as a support act, and thus join her on Glad To Be Here and The Ride respectively. Trisha Yearwood remains an inspiration while Hillary Lindsay, as one of the best writers in town, is a guiding light too. More on them shortly.

Born in Iowa, Hailey wrote Ten Year Town, a fine summation of becoming a Nashville songwriter (although I love one argument that Nashville is so called because music is ten years behind). That song, written with the incomparable Brandy Clark, opens the album on a sombre note.

A host of publications loved the album – The Washington Post, Rolling Stone, Stereogum – so it’s not news to call this a great album. Look at the credits: as well as Brandy, there’s Lori McKenna. The pair team up again on two other tracks aside from Happy People: the album’s centrepiece Janice at the Hotel Bar, about a grandma offering advice to a younger lady to ‘make a good life’; and album closer Living The Dream, a gorgeous tune about ‘the heartaches, the big breaks, the wrong turns, the mistakes’ which all form part of life. It bookends the album nicely and it’s good to end on a high note.

Hillary Lindsey was in the room for reminiscin’ song The Days (‘make em count’) and The Faker, a stark acoustic ballad expertly strummed and featuring the rhyme of ‘sceptre/jester’ (Hillary’s the best in town and has been nominated for the Songwriter award at the ACMs. She may well beat Josh Osborne, Ashley Gorley, Hardy and Shane McAnally.)

Chris Stapleton (nominated for Male and Entertainer at the ACMs) is found on The Dream because his song The Devil Always Made Me Think Twice was a cut on it before it appeared on Starting Over. Hailey’s version is in a lower key (B minor) and is produced with a louder arrangement than Chris’ version. As well as Maren Morris, whose tone she shares, Hailey’s voice reminds me of Natalie Maines duetting with Kacey Musgraves, with vulnerability and power, as on the vocalised middle section of the bluesy afternoon drinkin’ triple-time song Red Wine and Blue, which I hope someone covers. It’s a singer’s song.

In fact, all of these songs are ripe for covering. I love the perky pair of Dream, Girl and All The Cool Girls, both of which have FM radio-friendly choruses that Harry Styles and Miley Cyrus are putting out now. Conversely, Loose Strings (given to her by, among others, Brent Cobb) is a break-up song where the vocal is right up front in the mix and Hailey’s voice teeters on sobriety, full of character.

The melody of Heartland (‘you gotta let your heart land’) reminds me of Kelsea Ballerini which makes sense as Forest Whitehead, Kelsea’s main collaborator for her first records, was in the room to write a song about being ‘on the rocks…pulling double shifts…waking up alone’.

As for the five new tunes, I love How Far Can It Go. It was written by Hailey, Hilary Lindsey and Nicolle Galyon (who runs the Songs & Daughters publishing house). Handily for a throwback song, they get a 90s icon, Trisha Yearwood, to sing about a time in the 90s when story songs were all over the radio. And fiddle, too: we get two bars of fiddle at the top of the song and a pair of teenage lovers who ‘are about to find out how far they can go’. It’s immediately evocative and leaps out of the stereo thanks to the production of Jake Gear and Hailey herself.

How To Break A Heart is a proper songwriter’s song, a list of ways to disappoint someone’s expectations. As you’d expect it’s full of humour: ‘don’t call back’ after a wonderful night; ‘put a diamond on her hand then call up your best man’. As with the Highwomen, the middle eight is sung in unison with three voices singing the same part: ‘What goes around comes back again, karma’s a bitch!’ With a banjo and some pedal steel in the back, as well as a vocalised outro to bellow along to, this is a country song and helps position Hailey as a breakout star who can slot into Miranda’s place in music should the Texan prioritise her marriage and her dogs over her music.

I would advise Little Big Town to take Hailey as a support act on their next visit to the UK. One day, like Kacey Musgraves, Hailey Whitters will have her name in the biggest font on the ticket. Remember the name, listen to The Dream.

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