In the live recording of "Maybe Not," Cat Power was at a pivotal moment in her career, having just released the album "You Are Free" in 2003. This album marked a significant turning point, showcasing her transition toward a more polished sound while still retaining the raw emotional core of her music. The performance captured in the video likely reflects the artistic evolution she was experiencing during this period, characterized by a blend of introspective lyrics and soulful melodies. Notably, Cat Power is known for her captivating live performances, often marked by her unique ability to connect deeply with her audience. The year following the album's release, she faced significant personal challenges, which further influenced her music and performances, making the live iteration of "Maybe Not" a poignant testament to her resilience and creativity during a transformative time in her life and career.