Songfacts®:

• Shadowboxing is boxing against an imaginary opponent. It's a way for boxers to train without getting hit.
  
  In this song, Fiona's lover-turned-"friend" has made her into a shadowboxer, ready for a fight but swinging at air because she's not sure what she's up against and when he's going to make his next move.
• Fiona Apple told Nuvo about this song: "It was because of this guy I had gone out with and had been really, really close with. I really loved him. I felt that he was my best friend. But he was a teenaged guy, and they don't think a lot of times. He mistreated me and then he came back. I couldn't even be friends with him for awhile. I cared about him, but it was just a situation where he kept trying to be friends with me, but I knew that he just wanted to be friends with me so he could have the option of making a move on me whenever he wanted to. Because I was so infatuated with him, and even in love with him, I was always available for that. It made me feel weak every time I would fall for that. And I would look forward to him making a move on me, but I knew that it was wrong. I knew that he was playing with me. And after awhile, I didn't even care anymore because I wanted him so much." >>

  Suggestion credit:
  Kristy - La Porte City, IA
• "Shadowboxer" was Apple's first single. Released ahead of her debut album, Tidal, it's a good representation of her sound, with a piano-and-strings arrangement framing her jazz-inflected vocal. Listeners were shocked to learn that Apple was just 18 years old - her lyrics and musical sensibilities indicated she had many more miles on her.
  
  Her label, Work (a division of Sony), knew she was a rare talent and pushed the song, but it was a tough sell: "Shadowboxer" runs 5:24 and doesn't have the big hooks that appeal to fans of pop music. Also, the video (directed by Jim Gable), was bare-bones black-and-white, more suited to VH1 than MTV. The song got some airplay on Adult Contemporary radio, but Apple's true appeal was to a younger audience that could absorb her pain. Most listeners found Apple through her song "Criminal," which came with a controversial video that earned her lots of airplay on MTV.
• Apple performed this on Saturday Night Live when she was the musical guest on the November 16, 1996 episode.