10 Best George Strait Songs of All Time - Singersroom.com

About the Song

When it comes to country music that blends charm, subtle humor, and effortless storytelling, George Strait is in a league of his own. With a career spanning over four decades and more than 60 number-one hits, he has earned the title of “King of Country” through his ability to turn everyday emotions into timeless songs. In 1998, he released “We Really Shouldn’t Be Doing This,” a lighthearted and clever track from his album One Step at a Time, proving once again that he could capture complex human feelings with disarming simplicity.

At just over two minutes long, the song is a short and witty reflection on temptation and undeniable attraction. Rather than diving into heavy drama, George Strait approaches the theme with a playful wink, portraying two people who know they probably shouldn’t give in to their chemistry, but can’t help acknowledging the spark between them. His smooth, conversational delivery makes the listener feel as though they’re part of the story — sharing in the mischievous grin and the unspoken tension.

Musically, “We Really Shouldn’t Be Doing This” is classic George Strait: traditional country instrumentation with acoustic guitar, steel guitar flourishes, and a toe-tapping rhythm that keeps the song breezy and fun. There’s no overproduction or unnecessary flash; instead, the arrangement perfectly mirrors the song’s casual, flirtatious tone. It’s a masterclass in how less can truly be more in country storytelling.

What makes the track memorable is its relatability and charm. Everyone has experienced a moment of playful conflict between what the heart wants and what common sense dictates. George Strait takes that universal experience and distills it into a song that’s both clever and warm, never crossing into melodrama. It’s a testament to his skill as a storyteller — he can take a seemingly simple premise and turn it into a memorable country classic.

Over the years, “We Really Shouldn’t Be Doing This” has become a fan favorite for its mix of wit, authenticity, and that signature Strait smoothness. It reminds us why George Strait’s music continues to resonate across generations: he makes life’s small, familiar moments feel like songs we’ve known forever.

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