Jessie James Decker Shakes Off Heartbreak In Confident New Single, ‘Should Have Known Better’

Jessie James Decker’s long-awaited new country single has arrived.  The singer/songwriter/personality recently released “Should Have Known Better,” a feisty breakup…


Lauren Jo Black

| Posted on

August 23, 2021


2:45 pm

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Photo Courtesy Jessie James Decker

Jessie James Decker’s long-awaited new country single has arrived. 

The singer/songwriter/personality recently released “Should Have Known Better,” a feisty breakup anthem that find Decker feeling more self-assured than ever before as she bids farewell to an ex. 

“Should have known better than to break my heart/ Oh, ain’t it funny/ No, I never looked better and it’s all your fault/ Oh, sorry, honey/ But it’s over, yeah, I moved on, hallelujah, hallelujah/ Should have known better than to break my heart,” sings sings on the pop/country infused chorus. 

YouTube video

“I’ve had my heart broken before – we all have, at some point in our lives,” Decker shared in a statement. “It doesn’t matter if it’s from a relationship ending or from people trying to tear you down. This song is all about not letting that pain break you and coming out of it on the other side strong and confident. Anyone who broke your heart will regret it most when you SHINE! Now roll those windows down and sing it at the top of your lungs!”

Decker brought the song to life with a brand new music video. Directed by Kevin + King and shot in Joshua Tree, Decker belts out the powerful lyrics as she sheds the memories of a love gone wrong. 


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A post shared by Jessie James Decker (@jessiejamesdecker)

The Kittenish founder celebrated the release of the single with a quick getaway to the beach over the weekend. 

“Eric wanted to celebrate my new song coming out, so he said let’s go down to the gulf and enjoy some sunshine, family, food and beach time,” she wrote on Instagram. 

This is the first taste of new music from the Big Yellow Dog / Atlantic Records / Warner Music Nashville recording artist. Additional releases and tour dates are expected to be announced soon. 

Click above to watch Jessie James Decker’s “Should Have Known Better” music video. 

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Lauren Jo Black

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Lauren Jo Black

Lauren Jo Black, a University of Central Florida graduate, has immersed herself in the world of country music for over 15 years. In 2008, she co-founded CountryMusicIsLove, eventually selling it to a major record label in 2015. Following the rebranding of the website to Sounds Like Nashville, Black served as Editor-in-Chief for two and a half years. Currently, she assumes the role of Editor-in-Chief at Country Now and oversees Country Now’s content and digital footprint. Her extensive experience also encompasses her previous role as a Country Music Expert Writer for and her work being featured on She’s been spotlighted among Country Aircheck’s Women of Influence and received the 2012 Rising Star Award from the University of Central Florida. Black also spent time in front of the camera as host of Country Now Live, which brought live music directly to fans in 2021 when the majority of concerts were halted due to the pandemic. During this time, she hosted 24 weeks of live concerts via Country Now Live on Twitch with special guests such as Lady A, Dierks Bentley, Jordan Davis, Brett Young, and Jon Pardi. Over the course of her career, she has had the privilege of conducting interviews with some of the industry’s most prominent stars, including Reba McEntire, Blake Shelton, Luke Combs, Carrie Underwood, Luke Bryan, Miranda Lambert, Lainey Wilson, and many others. Lauren Jo Black is a longtime member of the Country Music Association and the Academy of Country Music.