Released in 1999 as part of Toby Keith’s album How Do You Like Me Now?!, You Shouldn’t Kiss Me Like This is a country song that would solidify Keith’s place among country music’s biggest stars. Written by Keith himself, the song explores the complex emotions of a man drawn to a woman already in a relationship.

You Shouldn’t Kiss Me Like This wasn’t just written by Keith, but produced by James Stroud alongside Keith himself. Stroud, known for his work with artists like Wynonna Judd and Ronnie Milsap, would help shape the sonic landscape of the song.

The song’s narrative centers around a man wrestling with his feelings for a woman who isn’t available. The lyrics paint a picture of stolen glances, late-night encounters, and the internal conflict of wanting something that can’t be. You Shouldn’t Kiss Me Like This struck a chord with audiences, likely due to its relatable portrayal of emotional entanglement.

You Shouldn’t Kiss Me Like This became a massive commercial success. The song reached number one on the Billboard Hot Country Singles chart and climbed to number two on the prestigious Billboard Hot 100 chart. This crossover success, landing high on a chart that typically showcases pop music, brought Toby Keith to a wider audience and solidified his status as a country music powerhouse.

Critical reception for You Shouldn’t Kiss Me Like This was also positive. Reviewers praised the song’s emotional depth and catchy melody. Some highlighted Keith’s distinctive vocals, which added a layer of authenticity to the song’s narrative. The song’s critical and commercial success helped propel Keith’s career to new heights, solidifying his position as a major force in country music.

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