In the live performance of "I'm Gonna Miss Her" on *The Late Show with David Letterman*, Brad Paisley was in a notable phase of his career. This performance aired in 2002, shortly after the release of his critically acclaimed album *Part II*, which came out in 2001. This album solidified Paisley’s standing in the country music genre, featuring hits that blended traditional and contemporary elements. "I'm Gonna Miss Her," one of its standout tracks, showcases his distinctive guitar work and clever songwriting, reflecting his signature style that appeals widely to fans. During this period, Paisley was also gaining recognition for his charismatic stage presence, which is evident in this live performance. This era marked a turning point for Paisley, as he began to elevate his profile in the country music scene, setting the stage for his subsequent success and numerous awards in the years that followed.