"Left and Leaving" is a song by the Canadian band The Weakerthans, featured on their 2000 album of the same name. The track explores themes of loss, longing, and the emotional weight of leaving a place or person behind. Its poignant lyrics resonate with listeners, capturing the bittersweet nature of farewells. The song is characterized by its melodic structure and introspective tone, showcasing John K. Samson's distinctive vocal style and songwriting. "Left and Leaving" has become a significant piece in the band's discography, often celebrated for its relatable narrative and heartfelt delivery.