4 Lee Ann Womack Songs That Still Always Make Me Cry

Lee Ann Womack has released plenty of different kinds of songs over the years, from the inspirational “I Hope You Dance” to the comedic “I’ll Think Of A Reason Later”. But included in Womack’s lengthy repertoire of songs are some truly sad ones.

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These four Lee Ann Womack songs will always make me cry.

“Twenty Years And Two Husbands Ago”

Out in 2005, “Twenty Years And Two Husbands Ago” sheds a light on the pain of aging. It also highlights the overwhelming the sting of regret. On Womack’s There’s More Where That Came From record, Womack wrote the song with Dean Dillon and Dale Dodson.

“Twenty Years And Two Husbands Ago” says, “Lookin’ in the bathroom mirror puttin’ my makeup on / Maybelline can’t hide the lines of time that’s gone / I weighed 105 soakin’ wet, I’d knock ’em dead in that sun dress / Had it all just too young to know / That was twenty years and, two husbands ago I remember when he took my hand and said ‘I do’ / And the kitchen I was standing in, when he said ‘I’m through’ / And I swore I’d never fall back in, put my heart through that again / Never let somebody get that close / But that was twenty years and, two husbands ago.”

“The Fool”

The Fool” is Lee Ann Womack’s second single, and her first No. 1 hit. On her self-titled freshman record, Marla Cannon-Goodman, Gene Ellsworth, and Charlie Stefl are the three writers.

“The Fool” is about a woman who stays with a man, even though she knows he’s in love with someone else. Sung from the perspective of the woman still with him, the song says, “If you’ve got a minute, I’ll buy you a drink / I’ve got something to say / It might sound crazy, but last night in his sleep / I heard him call out your name / This ain’t the first time he’s done it before / And it’s hard to face the truth / I’m the fool in love with the fool / Who’s still in love with you.”

“A Little Past Little Rock”

“A Little Past Little Rock” is written by Brett Jones, Tony Lane, and Jess Brown. The song, out in 1998, is the debut single from Womack’s sophomore Some Things I Know record.

A heartbreaking song about moving from Dallas to help get over someone after the relationship ends, “A Little Past Little Rock” says, “I’ve got to keep my heart out of this / And both hands on the wheel / I’m learning more with every mile / Just how leaving feels / It’s a lonely stretch of blacktop / Out into the blue / Don’t know where I’ll go / Or what I’ll do / I’m a little past Little Rock / But a long way from over you.”

“Last Call”

Erin Enderlin and Shane McAnally are the two writers on Womack’s “Last Call”. The song, out in 2008, is on Call Me Crazy. “Last Call” is about the heartache that comes with being in love with an alcoholic, who only calls when he’s been drinking.

“Last Call” says, “I bet you’re in a bar / Listening to a country song / Glass of Johnny Walker Red / With no one to take you home / They’re probably closing down / Saying, ‘No more alcohol’ / I bet you’re in a bar / ‘Cause I’m always your last call.”

A hit for Womack, McAnally reveals he and Enderlin actually thought “Last Call” was going to be an entirely different song. They didn’t realize what the title would be until they were writing it.

“I actually was convinced that ‘I bet you’re in a bar’ was the title of the song,” he tells The Boot. “The hook, ‘Last Call,’ later unveiled itself, and the rest is country music history.”

Photo by Jesse Grant/WireImage

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