Album Review – Hailey Whitters – “Living The Dream (Deluxe)”

Normally you don’t want your name going into the history books with an asterisk beside it. That usually denotes something unsavory or unscrupulous. But for Hailey Whitters and some of the other women who hit Nashville right at the wrong time—namely when Bro-Country was having its way with the country genre—they deserve some notation for the rigors they endured trying to get heard during one of commercial country’s most awful eras.

The Dream by Hailey Whitters was originally released in February of 2020, and was bookended by sentiments about the disillusionment of high hopes for country music stardom being impaled on the jagged ends of Nashville’s inhospitable palisades. Widely respected by peers and regarded highly by critics, 12 years in town and Hailey still had to fight tooth and nail just to be heard and have rent in hand every month, even after having written songs for the likes of Alan Jackson and Little Big Town.

But instead of just bellyaching, Hailey turned these frustrations and fleeting hopes into the inspiration for the excellent song “Ten Year Town.” Not an entirely new idea, but telling and touching in a way that finally had Hailey on the radar of many, it was the first taste from The Dream, which ultimately worked as a showcase for Hailey’s dexterity as a performer and songwriter, from “Janice At The Hotel Bar” that had a very Lori McKenna-style wisdom-infused narrative to it, to the gritty “The Devil Always Made Me Think Twice,” which gave you Ray Wylie Hubbard vibes, and was later cut by co-writer Chris Stapleton for his Starting Over record.

The Dream received much praise and deservedly so. Stripping down two of the best songs on the album in “Ten Year Town” and “The Faker” really exposed what a stellar songwriter Hailey Whitters was, and the final song “Living The Dream” was the perfect encapsulation for what Whitters wanted to say.

“The dream is a paycheck at the end of the week
Waitin’ tables, makin’ small talk out back on your break
The dream is a one bedroom walk-up apartment
Cheap Christmas lights out on the fire escape“

But if we were being honest, there was still a little something missing from The Dream, non-deluxe. More Americana in the production and approach—and with the songs “Dream, Girl” and “All The Cool Girls” veering into the pop realm—as good as The Dream was, it still pulled up just short of making the full case of why Hailey Whitters was somebody country music should fully embrace.

Deluxe editions of albums are often repositories for whatever might have been left on the cutting house floor after the original track list was finalized, with maybe one or two new songs recorded afterward that you don’t think are good enough to hold back for the next record. But with Hailey’s Living The Dream (Deluxe Edition), it’s so much more. The new songs fulfill the lingering desires we had for The Dream, including specifically more country-sounding material that we knew Whitters was capable of. It takes a really good album and makes it a great one.

All five of the new songs feel like home runs. They’re all songs that in a just world, would get their fair chance on country radio, while they also highlight just how revered Hailey Whitters is with the rest of her fellow performers and songwriters since each one is a collaboration.

Little Big Town is not known for their traditional country, but Hailey ropes them into the fiddle-driven “Fillin’ My Cup” that makes for an excellent little country song. Hailey Whitters collaborating with Brent Cobb? Even with Brent singing a little higher than what is probably in his comfort zone, this song about seeing the good in life is a perfect counter-balance to the more dour material of the non-deluxe edition of the original album.

“How To Break a Heart” is another great one with Lori McKenna and Hillary Lindsey, making Hailey Whitters and honorary Love Junky. And “How Far Could It Go” with Trisha Yearwood could be like the second chapter to “She’s In Love With The Boy.”

The Dream made the case for Hailey Whitters as one of mainstream country music’s greatest songwriters who’d been unceremoniously overlooked and served a raw deal due to the situations and circumstances she faced when she showed up to Nashville. Living The Dream shows she’s also one of our finest country entertainers, if she would just be given the opportunity. Living The Dream (Deluxe Edition) makes the full-bodied case for Hailey Whitters, no asterisk required.

8.5/10

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Purchase Living The Dream (Deluxe Edition)