Lee Ann Womack

The Best Lee Ann Womack Songs

August 19, 2021 12:30 pm GMT
Last Edited June 23, 2023 4:43 pm GMT

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Lee Ann Womack has always gone with her gut.

She blew into Nashville as a Texas traditionalist who knew how to meet the business halfway, going as commercial as necessary to land on the radio while staying true to the history and craft of the music she lived and breathed.

She could play by contemporary standards, but always with a nod to the past.

Holler’s chronological list to her career includes big singles and favourite album tracks from a bespoke catalogue that has barely taken a misstep in close to 25 years:

UMG Recordings Inc. | 1997

Never Again, Again

Womack's wonderful entrée single from her platinum-selling debut declared her intention to respect country's historic sound while showcasing a lyrical dexterity more in keeping with contemporary compositions.

It introduced supple vocal skills strongly reminiscent of Dolly Parton, whose records Womack had been schooled in, along with influential touches from the artists her DJ father had played growing up: Ray Price, George Jones and others.

'Never Again, Again' dared to play in waltz tempo, was too old-school for some and was only a medium-sized hit. But to admirers, it evoked Loretta, Tammy and the greats, and was feted by Billboard as “wonderful, tear-in-the-throat, honest-to-God country music”.

UMG Recordings Inc. | 1997

The Fool

Womack's first big country hit was the first of four No. 2 singles, as she established the frequent recording persona of the reflective, wounded and entirely relatable loser in love.

She confessed that she needed persuading by label executives to cut it, telling Billboard, "I'm sorry I didn't hear it the first time but boy, I'm glad I had the sense to listen to people who knew what they were talking about”.

UMG Recordings Inc. | 1998

I'll Think Of A Reason Later

From her second album, this Tony Martin / Tim Nichols song was the fourth of those No. 2 hits (after 'You've Got To Talk To Me' and 'A Little Past Little Rock').

It was perfect pop-edged country of its day, combining catchy hooks, Womack's engaging delivery and hilarious, wish-I'd-thought-of-that lyrics, which country has always done so well.

UMG Recordings Inc. | 1998

I Keep Forgetting

The twanging guitar and fiddle features of this album track have listeners hooked in precisely five seconds, and when Vince Gill joins Womack for the chorus harmonies, resistance is futile.

As always, she lives for the lovelorn lyric, on a number written by Jamie O'Hara — the former member of hitmakers the O'Kanes — who died early in 2021.

MCA Nashville | 2000

I Hope You Dance

To call this indelible ballad a “career record” is almost to denigrate dozens of other delights in Womack's body of work, and she came to be a little wary of its almost evangelistic aura.

But it's undeniably inspiring all the same: a multi-format smash that spread her name around the world, sold a million US copies physically and another million digitally, and scooped up every award going, including Best Country Song at the Grammys.

MCA Nashville | 2000

Ashes By Now

From the same best-selling album, Womack included a fine version of the tune first written and recorded by Rodney Crowell, and then soon afterwards by his friend Emmylou Harris.

In Womack's hands, it helped bring together the old and new schools of country, like estranged family members making up at a wedding.

MCA Nashville | 2004

Mendocino Country Line

Scandalously overlooked on the UK charts, this was written by Matt Serletic and Bernie Taupin, who brought their very best imagery to a vivid depiction of the great outdoors.

It became the banner track on Willie Nelson's 2002 album The Great Divide and his first country hit in over a decade. Thanks to the brilliant casting of Womack as his fellow vocalist, the single also won a Grammy for Best Country Collaboration.

MCA Nashville | 2002

When You Gonna Run To Me

In the wake of her pop crossover, Womack's fourth album was something of a hybrid of styles, and her first not to offer up a major hit. As such, it doesn't sit fondly in her memory, but it's nevertheless full of elegantly crafted performances of songs by Gretchen Peters, Julie Miller, Bruce Robison and others.

It included this lovely surprise of breezy pop confection; one which you can almost imagine Kacey Musgraves shining her disco mirrorball to for a new version.

MCA Nashville | 2002

He'll Be Back

Co-written by the prolific and, by then, veteran country composer-artist Hank Cochran, this was another one of those gorgeous heartbreak tunes at which Womack has always reigned supreme.

Yes, her man left this morning, but “If he's anything like his memory, he'll be back”. What a line.

MCA Nashville | 2002

Closing This Memory Down

This hidden gem, written by the vastly experienced A-team of Dave Loggins and John Bettis, is a truly admirable and sophisticated address on adult relationships.

It's goosebumps from start to finish, with Womack in magisterial but understated form as she wearily shuts down an affair that's gone out of business.

“There's nobody home”, she tells her former lover in resignation. “I think you're lookin' for someone or something that's either missin' or gone”.

MCA Nashville | 2005

There's More Where That Came From

Womack restored her focus on her sixth studio album, for which her admirable chief intent was simply to have fun and to be herself. The result was a marvellous collection of real-life narratives on love, loss, cheating, drinking and everything she, and her loyal listeners, love about real country music.

The reward was the CMA Album of the Year title. This opener, in which the singer not only faces up to but celebrates her sins, was co-written by Chris DuBois and a pre-stardom Chris Stapleton.

MCA Nashville | 2005

I May Hate Myself In The Morning

The theme of approaching sin honestly continued on this thoroughly superior cheating ballad, a skillful depiction of an illicit entanglement that's both realistic and richly romantic.

It's helped no end by sumptuous fiddle and pedal steel, as well as a particularly sexy video. Written by Odie Blackmon, it became Womack's most recent country top-ten single.

MCA Nashville | 2005

Twenty Years And Two Husbands Ago

With a title that sounds like it comes from a Joan Rivers sketch, this track simply demands a listen. Womack, who has accrued more co-writes as she's gone along her country music career, added one more with this track, which she penned with Dale Dodson and the much-covered Dean Dillon, a combination we'll hear again shortly.

MCA Nashville | 2007

Last Call

Now paired with heavyweight producer Tony Brown, Call Me Crazy had country tradition as its bassline, while Womack stepped into contemporary territory.

Listen to 'The Bees,' written by Natalie Hemby and Daniel Tashian - alongside background vocals from Keith Urban - as an example of its experimentation. This rueful single, meanwhile, was the record's one top 20 entry.

MCA Nashville | 2007

Either Way

Unafraid to be sombre when the lyric called for it, Womack cut this original. Chris Stapleton co-wrote the track, which his latter-day faithful will recognise from his own version on From A Room: Volume 1.

The sentiment, and the performance, describe the desperation of a supposedly perfect couple whose life together is actually broken beyond repair.

MCA Nashville | 2007

Everything But Quits

Womack’s albums are uniquely fuelled by songs that tell life as it really is. Another on Call Me Crazy is the touching 'Have You Seen That Girl', in which the singer searches high and low for the person she used to be.

She wrote it, again, with Dale Dodson and frequent George Strait confidant Dean Dillon, leading to this splendid palate-cleanser between Womack and the King of Country.

Sugar Hill Records | 2014

All His Saints

Womack's albums have always contained plenty of gospel, all the way back to her first album's 'Get Up In Jesus' Name'.

By way of acknowledging another vital ingredient in her musical make-up, here's a Mindy Smith tune from 2014 (released on Sugar Hill after her departure from MCA) that saw her turning ever more rootsy. She sings the heaven and hell out of it.

Sugar Hill Records | 2014

Out On The Weekend

It's hard to think of anyone with a hit-laden, multi-platinum country background who can make things quite as dark as Womack, most often on songs of self-reproach about the narrator's wicked ways.

Sounds Like Nashville called this Adam Wright composition “a scalding psychic meltdown of a lost soul”, and the resonant, string-laden arrangement is suitably murky.

ATO Records | 2017


To end with, two songs from the exemplary Americana album that saw Womack leaving Nashville to explore the cleaner creative air of Houston.

The Lonely, The Lonesome & The Gone cast her in a new, yet old, light and won her a ton of new admirers. She had a career-high seven co-writes on it, including this elegant collaboration with Adam Wright and Waylon Payne.

ATO Records | 2017


The writing combination with Wright and Payne rode into town again here and, as throughout, her vocal judgement and impact are unimpeachable.

It's a long road from 'Never Again, Again', and yet Lee Ann Womack's stayed true to herself from that day to this.

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Written by Paul Sexton
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