Already a mother of four by the time she was 20, Loretta Lynn (born Loretta Webb) drew from her Butcher Hollow, Kentucky roots and life as a young wife and mother to write and record songs that spoke to the American woman. Over her 50 year career, Lynn racked up 24 No. 1 singles and became one of the most influential artists in country music.
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Lynn wasn't one to shy away from singing about issues facing everyday people. She sang about the Vietnam War ("Dear Uncle Sam"), sexism ("Rated X") and contraception ("The Pill"). Her best songs often drew from her own life story and her talent and fearlessness have continued to inspire the artists who've followed in her shoes.
Lynn was a trailblazer in more ways than one. She was the first woman to win the CMA for Entertainer of the Year and through her fearless songs she inspired countless artists, from Reba McEntire to Miranda Lambert.
In the past 20 years, she released some of her best work -- 2016's Full Circle, 2018's Wouldn't It Be Great and 2021's Still Woman Enough.
On Oct. 4, 2022, Lynn passed away at the age of 90 at her home in Hurricane Mills, Tennessee. Today, we remember the iconic country singer with 20 essential Loretta Lynn songs -- all of which are a reminder of the Grammy-winning Country Music Hall of Fame member's enduring legacy.
20. "I Wanna Be Free"
Lynn longs for liberation from heartache on "I Wanna Be Free," an anthemic ode to moving on.
"When my baby left me everything died/ But a little bluebird was singin' just outside' Singin' tweedle-dee-dee, fly away with me," Lynn sings. "Well you know I think I'm a gonna live/ Gotta lotta love left in me to give/ So I want to be free"
19. "Wine, Women and Song"
No stranger to songs about philandering men, Lynn recorded "Wine, Women and Song," written by Betty Sue Perry, in 1964.
The tune featured the clever turns of phrase that defined Lynn.
"While I'm a-makin' beds you're out makin' time," Lynn sings. "You rob my piggy bank and spend my last thin dime on wine, women and song."
But, as usual, Lynn gets the last laugh, promising that "one of these nights, you're gonna come/ you'll find it's comin' home to you/ You'll see what you've done/ and what's good for one is also good for two."
18. "When the Tingle Becomes a Chill"
This steel-laden country heartbreaker, penned by Lola Jean Dillon, finds Lynn reflecting on a love that's gone cold. ("I never wanted to stop loving you," Lynn sings. "I swear by the breath in my body that's true." It's a reminder that the country icon was as skilled as a song interpreter as she was a songwriter.
17. "Somebody, Somewhere (Don't Know What He's Missin' Tonight"
Lynn's voice aches with yearning on this track written by Lola Jean Dillon, "Somebody Somewhere (Don't Know What He's Missin' Tonight)," recorded in 1976.
16. "Wings Upon Your Horns"
Lynn laments spending a night with a misleading man in this song written and recorded by the country queen in 1969. The song slyly hints at a loss of innocence as Lynn narrates a story about going "from an innocent country girl to a woman of the world."
"You hung my wings up on your horns, turned my halo into thorns and turned me into a woman I can't stand," Lynn sings on the searing tune.
15. "Trouble in Paradise"
Written by Kenny O'Dell, "Trouble in Paradise" was Lynn's eighth No. 1 single. The grooved-up 1974 single found Lynn exploring familiar themes of infidelity.
14. "You're Lookin' At Country"
Lynn was proud of her Butcher Holler roots and she made it clear in her cheeky 1971 hit "You're Lookin' at Country." Lynn has said that she got the inspiration to write the song while touring throughout the states.
13. "Mr. and Mrs. Used to Be"
Before she burned up the charts with Conway Twitty, Loretta Lynn recorded a series of duets with her friend Ernest Tubb. "Mr. and Mrs. Used to Be," from the album of the same name, hit No. 11 on the country charts in 1964.
12. "Hey Loretta"
Lynn's 1973 hit "Hey Loretta," penned by Shel Silverstein, features some of the singer's most daring lines. Fed up with being treated like a maid by her husband, the song's narrator threatens to leave him for a brand new life filled with new men and more glamour. "You can feed the chickens/you can milk the cow," Lynn sings with a wink. "This woman's liberation is gonna start right now."
11. "Rated X"
Written and recorded by Lynn in 1972, "Rated X" detailed the double standards placed upon women. Though it was considered controversial at the time, that didn't stop it from going to No. 1 on the country charts.
10. "Louisiana Woman, Mississippi Man"
Lynn and Conway Twitty were frequent duet partners throughout the 1970s and '80s, scoring hits with "After the Fire is Gone" and "As Soon as I Hang Up the Phone." The rollicking "Louisiana Woman, Mississippi Man," the dynamic duo's third single, went to No. 1 in 1973. The duo teamed up for a slew of duet albums, including 1972's Lead Me On and 1975's Feelins'.
9. "Blue Kentucky Girl"
Written by Johnny Mullins, "Blue Kentucky Girl" was released by Lynn in 1965 and became one of her earliest top 10 hits.
8. "Portland, Oregon"
Teaming up with producer Jack White of the White Stripes, Lynn released her album, Van Lear Rose, in 2004. The record is a collection of Lynn's memories of growing up in Van Lear, Kentucky. From heartbreak ("Miss Being Mrs.") to spellbinding spoken word ("Little Red Shoes"), the album is Lynn at her best. But perhaps the album's brightest moment is the revved-up duet between Lynn and White, "Portland, Oregon."
7. "One's On the Way"
Another track penned by Shel Silverstein, "One's on the Way" is a tongue-in-cheek look into the life of a overworked mid-western mother who spends her days comparing her life to the lives of various glamorous women, from Jackie Kennedy to Elizabeth Taylor.
6. "Don't Come Home A-Drinkin' (With Lovin' On Your Mind)"
One of many songs inspired by Lynn's marriage to Doolittle Lynn, "Don't Come Home A-Drinkin' (With Lovin' On Your Mind)" was Lynn's first No. 1 hit.
5. "I'm a Honky Tonk Girl"
One of the first songs Lynn ever wrote, "I'm a Honky Tonk Girl" was released in 1960. Lynn and her husband traveled across the United States to self-promote the single at various radio stations. By the time the couple arrived in Nashville, the song was a hit.
4. "The Pill"
One of the few country songs to openly discuss birth control, "The Pill" is one of Lynn's most controversial songs. The song was a top 5 hit in 1975 and is considered one of Lynn's signature songs.
3. "Fist City"
One of her sassiest songs ever recorded, "Fist City" found Lynn ready to do battle with a woman showing a little too much interest in her husband. The song hit No. 1 in 1968.
2. "You Ain't Woman Enough (To Take My Man)"
Another feisty track that proved to any doubters that Lynn was not to be messed with, "You Ain't Woman Enough (To Take My Man)" went to No. 2 in 2966. Lynn's close friend and mentor Patsy Cline encouraged her to release the song.
1. "Coal Miner's Daughter"
Her most autobiographic song, "Coal Miner's Daughter," which would go on to double as the title of Lynn's autobiography and a film starring Sissy Spacek as Lynn, captures what we all love about Loretta Lynn: her talent, songwriting prowess, honesty and appreciation for her roots. In just three minutes, the song sums up Lynn's incredible life and the career that made her a country icon.
This story previously ran on April 14, 2020. It was updated on Oct. 4, 2022.
READ MORE: Loretta Lynn's Siblings: Then and Now
