Country Singer-Songwriters Whey Jennings & Karen Waldrup Collaborate On Potential Sleeper Duet Hit, Delivering Heartbreak & Harmony In Powerful New Music Video For “Damned If I Stay”

“…perfectly encapsulates the dilemma of being stuck in a toxic relationship.” 

– Saving Country Music

“…largely autobiographical new record.”– American Songwriter

“I’ve listened to all your albums, all your past music. This is the best album.”– Rock & Review with Eric Dahl

“…one of his most personal and powerful releases…”– Nashville.com

NASHVILLE, Tenn. (June 18, 2026) – Nashville recording artist and country singer-songwriter Whey Jennings collaborates with rising country recording artist and former The Voice standout Karen Waldrup for the emotionally charged duet “Damned If I Stay.” The track is featured on Jennings’ latest album, Baptized By Fire [stream/download], available everywhere digitally by Dirt Rock Empire. 

Jennings & Waldrup jointly premiered their new performance video today on theirYouTube channels[@WheyJennings] & [@KarenWaldrup]. The video is also scheduled to begin airing on American Country Network [watch here] on June 22 at 8:17am & 11:17pm EST.

“Damned If I Stay” blends contemporary country production with the timeless chemistry of a classic country duet, and explores the emotional tug-of-war of a relationship falling apart when neither staying nor leaving feels right. The collaboration marks the first musical pairing between Jennings and Waldrup, whose vocal contrast and emotional delivery bring added depth and realism to the song’s theme.

“‘Damned If I Stay’ is about being caught between staying and leaving when both choices hurt,” Jennings said. “It’s that tension a lot of people don’t talk about. This song called for a duet, and Karen’s voice added the contrast that helped bring the full emotion of the story to life.

“…perfectly encapsulates the dilemma of being stuck in a toxic relationship.” – Saving Country Music“…largely autobiographical new record.”– American Songwriter“I’ve listened to all your albums, all your past music. This is the best album.”– Rock & Review with Eric Dahl “…one of his most personal and powerful releases…”– Nashville.com NASHVILLE, Tenn. (June 18, 2026) – Nashville recording artist and country singer-songwriter Whey Jennings collaborates with rising country recording artist and former The Voice standout Karen Waldrup for the emotionally charged duet “Damned If I Stay.” The track is featured on Jennings’ latest album, Baptized By Fire [stream/download], available everywhere digitally by Dirt Rock Empire.  Jennings & Waldrup jointly premiered their new performance video today on theirYouTube channels[@WheyJennings] & [@KarenWaldrup]. The video is also scheduled to begin airing on American Country Network [watch here] on June 22 at 8:17am & 11:17pm EST. “Damned If I Stay” blends contemporary country production with the timeless chemistry of a classic country duet, and explores the emotional tug-of-war of a relationship falling apart when neither staying nor leaving feels right. The collaboration marks the first musical pairing between Jennings and Waldrup, whose vocal contrast and emotional delivery bring added depth and realism to the song’s theme. “‘Damned If I Stay’ is about being caught between staying and leaving when both choices hurt,” Jennings said. “It’s that tension a lot of people don’t talk about. This song called for a duet, and Karen’s voice added the contrast that helped bring the full emotion of the story to life.[“Damned If I Stay” Performance Video | SHARE/EMBED: YouTube]Produced by Gary Carter at Danny Parks’ Long Hollow Studio, the track features an acclaimed lineup of Nashville musicians, including Grand Ole Opry band member Danny Parks on guitar, ACM Keyboard Player of the Year winner Mike Rojas (Ricky Skaggs, Hank Williams Jr.) on piano and organ, Joel Key (Cody Johnson, Thomas Rhett, Toby Keith) on acoustic guitar, Gary Carter on steel guitar, Deanie Richardson (Del McCoury Band, Hank Williams Jr., Marty Stuart) on fiddle, and Garth Justice (Reba McEntire, Jo Dee Messina) on percussion. “Writing this song with Whey Jennings was such a career highlight for me,” Waldrup said. “He is such an emotional singer and that’s what this song needed. I have such a special friendship with Whey and it’s incredible to see that friendship spotlighted on such a personal song for both of us from our own life experiences.” Baptized By Fire Track Listing & Songwriters:1. “Wrong For The Time” (Jim “Moose” Brown, Whey Jennings, David Wade)2. ”What Lovin’ You Does” (Dustin Spears)3. “Can’t Outrun A Train” (Jack Dempsey)4. “Damned If I Stay” (Whey Jennings, David Wade, Karen Waldrup)5. “A Whole Lotta Nothin’” (Whey Jennings, Wes Shipp)6. “Force Of Nature” (Whey Jennings, Wes Shipp)7. “Whichever Way The Wind Blows” (Whey Jennings, Tyler Booth, David Wade)8. “Wild Horses & Bad Habits” (Whey Jennings, Tyler Booth, David Wade, Kayla Ray)9. “I’ll See You Soon” (Whey Jennings, Wes Shipp)10. “Copperheads And Butterflies” (Whey Jennings, Tyler Booth, David Wade)11. “Take His Hand” (Whey Jennings, Dustin Spears)12. “Baptized By Fire” (Jim “Moose” Brown, Whey Jennings, David Wade) 2026 Baptized By Fire Tour Dates:JUN 20 – Hinton, Okla. [Info/Tickets]JUN 24 – Warrendale, Pa. [Info/Tickets]JUN 26 – Cadillac, Mich. [Info/Tickets]JUN 27 – Lima, Ohio [Info/Tickets]JUN 28 – Lebanon, Ohio [Info/Tickets]JUL 05 – Wadsworth, N.Y. [info/tickets]JUL 11 – Salisbury, Pa. [Info/Tickets]JUL 16 – Trout Creek, Mt. [Info/Tickets]JUL 17 – Riggins, Id. [Info/Tickets TBA] JUL 18 – Lewiston, Id. [Info/Tickets TBA]JUL 30 – Kittanning, Pa. [Info/Tickets]AUG 01 – Westtown, N.Y. [Info/Tickets]AUG 07 – Alden, N.Y. [Info/Tickets]AUG 08 – Alexandria, Pa. [Info/Tickets]AUG 09 – Miamisburg, Ohio [Info/Tickets]AUG 14 – Watseka, Ill. [Info/Tickets]AUG 15 – Cory, IN [Info/Tickets]AUG 16 – Belleville, Ill. [Info/Tickets]AUG 23 – Meadville, Pa. [info/tickets] AUG 28 – Clayville, N.Y. [info/tickets TBA] AUG 29 – North Ridgeville, Ohio [Info/Tickets]SEP 03 – Foxburg, Pa. [Info/Tickets]SEP 06 – Bellefontaine, Ohio [Info/Tickets]SEP 11 – Sunburg, Minn. [Info/Tickets]SEP 12 – Fond Du Lac, Wisc. [info/tickets TBA]SEP 18 – New Market, Tenn. [Info/Tickets]SEP 19 – Morehead, Ky. [Info/Tickets]OCT 16-18 – Ormond Beach, Fla. [Info/Tickets]OCT 31 – Powells Point, N.C. [Info/Tickets]NOV 06-08 – Galveston, Texas [Info/Tickets]Additional dates TBA on BandsInTown or WheyJennings.com/#tour**Appearance only About Whey Jennings: Country singer-songwriter Whey Jennings was born into one of country music’s most iconic family names, first emerging in 2012 as another naturally gifted singer from the Jennings tribe. With large boots to fill, the young Nashville recording artist and singer-songwriter for Dirt Rock Empire, with a booming baritone voice as big as Texas, finds himself with a few expectations to live up to. Seeking to establish his own musical legacy as one of the few remaining torch-bearing country traditionalists out there, Whey can instantly take his fans back to a time and sound his Grandfather Waylon and Grandmother Jessi gave birth to in the 70’s, even with his own songs. Jennings has three studio recorded EP releases under his belt, 2020’s Gypsy Soul, 2022’s If It Wasn’t for The Sinnin’, and 2023’s Just Before The Dawn. In the summer of 2024, Whey released his critically acclaimed, highly anticipated first full length album, Jekyll & Hyde, which premiered at #10 on Apple iTunes Top 40 Country Albums Chart, and #7 on iTopChart’s Top Country Music Album Chart. Jekyll & Hyde has been hailed by Fox News, Billboard, People Magazine, Forbes, Cowboys & Indians, Men’s Journal, Rodeo Life Magazine and recognized as one of the most anticipated albums of 2024 by SavingCountryMusic.com. His sophomore album, Baptized By Fire, is due out March 27, 2026. Many of Whey’s songs reveal real-life stories of how he has come to terms with and recovered from his checkered past of too much partying, led by a drug-fueled lifestyle. Songs about struggles, addiction, finding sobriety, and redemption through faith in God, family and his friends. Whey is forging his craft of straightforward songwriting and storytelling, while remaining a little rough around the edges. His unpolished grit and honest demeanor defines his sound, mixed with musical roots that run as deep as his famous Jennings family name would imply. # # #