100 Greatest Women, #99: Ashley Monroe

100 Greatest Women: 10th Anniversary Edition


Ashley Monroe

2008 Ranking: (New Entry)

Though country music is in her lineage— members of The Carter Family and Carl Smith are among her paternal relatives— Ashley Monroe has taken a circuitous route to country stardom. At just 11 years old, she performed a rendition of Patsy Montana’s “I Want to Be a Cowboy’s Sweetheart” at a talent contest in Pigeon Forge, Tennessee, which led to a recurring gig at one of the country music revues in the popular tourist destination. While that got Monroe’s foot in the door, it was her father’s death just two years later that proved a formative experience in her development into one of the aughts’ most widely regarded talents.

Following the death of her father, Monroe began writing songs as a means of coping with her family’s tragedy. In her late teens, she relocated to Nashville, where she built a reputation for her live performances around Lower Broadway and for her distinctive songwriting. While labels were initially resistant to signing her—this was between the Dixie Chicks’ exile from the genre and the emergence of teen phenom Taylor Swift, and women were beginning to fade from country radio— she eventually landed a deal with Sony in 2006. Her debut single, “Satisfied,” just missed the top 40, while a duet with Ronnie Dunn, “I Don’t Want To,” managed a #37 peak.

Unwilling to take a chance on an artist who hadn’t cracked the top 20 at radio, Sony buried her debut album, Satisfied, briefly releasing it only on digital platforms before pulling it altogether. Only when Monroe earned greater name recognition by the end of the decade did the album see another digital release in 2009, though even then, the label didn’t include “I Don’t Want To.”

In the interim, Monroe continued to build her reputation within the industry. She co-wrote noteworthy singles and album tracks for A-list acts like Jason Aldean (“The Truth”), Carrie Underwood (“Flat On the Floor”), and Miranda Lambert (“Heart Like Mine”). She also began collaborating with a wide range of artists, earning notice for her lithe harmony vocals on “Old Enough,” a single by Jack White’s side-gig, The Raconteurs, that was re-recorded as a bluegrass romp with genre legend Ricky Skaggs.

But it was her friendship with Lambert that perhaps led to Monroe’s breakthrough, as she and Lambert joined forces with Angaleena Presley to form the Pistol Annies in 2011. The trio received rave reviews for their album, Hell On Heels, which has sold nearly 500,000 copies to date, and they contributed performances to the soundtrack album for The Hunger Games and to Blake Shelton’s “Boys Round Here.”

With interest in Monroe reignited, Warner Brothers signed her to a new recording contract, and she released her sophomore album, Like a Rose, in 2013. Though radio was still resistant to her music, the album was hailed by critics as among the best of the year, and it did debut in the Top 10 Country Albums chart upon its release. The ribald third single, “Weed Instead of Roses,” peaked at #39 on Billboard’s Hot Country Songs chart thanks to the song’s popularity on streaming platforms.

Monroe’s voice was finally heard on country radio in 2015, when she was featured on Blake Shelton’s #1 hit, “Lonely Tonight,” which also gave her an opportunity to perform at the Academy of Country Music Awards and earned her nominations from the ACMs, CMAs, and Grammys. Sadly, radio’s interest proved short-lived, as “On To Something Good,” the lead single from her third album, 2015’s extraordinary The Blade, peaked at #53. Still, the album figured prominently in critics’ year-end lists, and The Blade earned Monroe her first nomination for Best Country Album at the Grammy Awards.

With a third album by the Pistol Annies and her fourth solo album, Sparrow, both slated for release in 2018, it’s still possible that Monroe could make further commercial inroads. While her commercial impact hasn’t kept pace with her talent, the quality of her output to date has established Monroe as one of contemporary country’s most vital artists.

Essential Singles

  • “Satisfied,” 2006
  • “I Don’t Want To,” 2006
  • “Hell On Heels” (with Pistol Annies), 2011
  • “Like a Rose,” 2013
  • “Weed Instead of Roses,” 2013
  • “The Blade,” 2015
  • “Hands On You,” 2018

Essential Albums

  • Hell On Heels (with Pistol Annies), 2011
  • Like a Rose, 2013
  • The Blade, 2015

100 Greatest Women: 10th Anniversary Edition

Next: #98. Gretchen Wilson

Previous: #100. Roba Stanley


  1. Ashley Monroe is a jem. It always frustrates me the mainstram ignored her as bad as they did. She represents what modern country music should sound like and I feel like she should be one of the females that are big right now, not the mediocre Kelsea Ballerini or the overrated Maren Morris.

    I am excited for what the future has for Ashley Monroe and I’m always happy when she releases new music.

  2. Ashley Monroe is one of the best talents currently in country music. Ashley has always been consistently putting great albums both solo and with the Pistol Annies. I hope Ashley finally breaks through as a big star because her talent is too good to pass up.

  3. I echo pretty much everything Raymond said. Ashley is by far one of the best female artists signed to a major label right now, imo. Her album, The Blade, is a great example of how more modern country should sound. As others have also mentioned before, she reminds me of a modern day Lee Ann Womack, both vocally and stylistically. Really looking forward to her new album, as it sounds very promising!

  4. Great write-up, Kevin. It’s exciting to see Monroe make her debut on this list.

    I first heard of her when she was featured in Country Weekly’s “Who’s New” column, and then shortly thereafter, “Satisfied” was featured as iTunes’ free Single of the Week. I downloaded it, and soon fell in love with it, and later with “I Don’t Want To” as well.

    I’m actually kind of proud of the fact that I knew of and liked Ashley Monroe since long before my blogging days, even though I was only in my early teens when she made her debut. I remember being puzzled and disappointed that I never heard her on the radio.

  5. Ashley is such a star. If this has back in the 90’s the song The Blade the song would have been career defining. Her last album is on my favorite of this decade. Mayflowers, From Time to Time and Bombshell are my other favorites.

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