Introduction
“Thinking About Leaving” is a song co-written and performed by American country artist Dwight Yoakam, in collaboration with songwriter Rodney Crowell. The track was featured on Yoakam’s 1999 compilation album, Last Chance for a Thousand Years: Dwight Yoakam’s Greatest Hits from the 90’s, which showcased his most notable hits from the decade alongside three new recordings, including this song.
Released as a single in 1999, “Thinking About Leaving” achieved moderate success on the charts, peaking at number 54 on the U.S. Country chart and number 59 on the Canadian Country chart.
The song’s lyrics delve into the complexities of a relationship on the brink of dissolution, capturing the internal conflict of contemplating departure while grappling with lingering emotions. This theme resonates with listeners, reflecting the universal struggle between holding on and letting go.
Critics and fans have praised “Thinking About Leaving” for its heartfelt lyrics and Yoakam’s emotive delivery. The song is often highlighted as a standout track on the compilation album, exemplifying Yoakam’s ability to convey deep emotional narratives through his music.
The official music video for “Thinking About Leaving” further enhances the song’s narrative, portraying the emotional turmoil of a relationship in decline. Yoakam’s performance in the video complements the song’s themes, offering a visual representation of the internal struggle depicted in the lyrics.
Over the years, “Thinking About Leaving” has maintained its relevance, continuing to resonate with audiences who appreciate its honest portrayal of relational complexities. The song stands as a testament to Dwight Yoakam’s enduring impact on the country music genre and his talent for crafting songs that speak to the human experience.