"Shadow" is the second single by American recording artist Ashlee Simpson, taken from her debut album, Autobiography (2004). The single peaked at #57 in the United States, becoming Simpson's second Billboard Hot 100 entry; it also peaked at #31 in Australia.

"Shadow" was written by Ashlee Simpson, Kara DioGuardi and producer John Shanks. It is three minutes and fifty-seven seconds long, and is the third track on Autobiography.

The song is about feelings Simpson had (when she was about 15 or 16 years old), according to one interview of living in the shadow of the dreams and accomplishments of her famous older sister, Jessica, and finding her own identity. Although "Shadow" is noted for having somewhat dark lyrics, it concludes with a positive message, as Simpson sings that "everything's cool now" and "the past is in the past." Simpson has said that it is "about loving yourself and coming to terms with who you are"; also, in an interview on Live with Regis and Kelly on September 22, 2004, Simpson explained the song's meaning:

"Shadow" was called the "best and most personal song" on the album in a People magazine review. There has, however, also been criticism of the song's lyrics for seeming excessively dramatic in light of Simpson's apparently loving family and fortunate circumstances.

Asked in one interview about the unhappiness she expresses in "Shadow" about her childhood, and whether it's "just for the song," Simpson replied:

Simpson also related, on another occasion, that "[w]hen my sister heard the song she cried and said, 'That's the most beautiful song I've ever heard!'"

The music video for "Shadow", directed by Liz Friedlander, also deals with the theme of the song. In the video, Simpson plays two different versions of herself, blonde and brunette, who live in separate "worlds" which exist side by side. The world of the blonde Ashlee appears happy and perfect, while the brunette Ashlee seems to have more negative feelings—at one point she shoves a bowl of cereal prepared by the blonde Ashlee off a kitchen table—but eventually it is revealed that the blonde Ashlee is not as happy as she seems. At the end of the video, shadows are seen leaving the brunette Ashlee. These scenes are intercut with Simpson singing in a living room setting with her band.

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