In the live performance of "Homeward Bound" featured in the SNL50 anniversary special, Paul Simon was celebrating a remarkable stage in his career, having established himself as a legendary figure in music. This event took place in 2025, marking the 50th anniversary of "Saturday Night Live." At this time, Simon's most recent studio album prior to the performance was "Stranger to Stranger," released in 2016, showcasing his continued innovation and relevance in the music scene. The choice of "Homeward Bound," a classic from his early solo career, highlights his enduring legacy and connection to the audience. Collaborating with Sabrina Carpenter during this performance also underscores Simon's openness to intertwining his classic works with contemporary artists, bridging generational gaps. Overall, this performance serves as a testament to Simon’s lasting influence in popular music.