"When You Awake" is a song written by Robbie Robertson and Richard Manuel that was first released on The Band's 1969 self-titled album The Band. A live performance was included on the Bob Dylan and The Band live album Before the Flood.

"When You Awake" is a ballad. The lyrics concern a young boy who received advice from "Ollie," who may be a friend or relative. Ollie tells the boy how difficult life can be; that the boy is a fool, that "it's a mean old world," to "Be careful where you step and watch what you eat." The boy turns to his grandfather for comfort, His grandfather's words comfort the boy by assuring him of his love, but do not contradict the harsh words from Ollie. Music critic Barney Hoskyns suggests that Ollie and the grandfather may be the same person. Robertson has stated that the song "is the story about someone who passes something on to you, and you pass it on to someone else. But it's something you take to heart and carry with you your whole life." According to music critic Nick DeRiso, the lyrics are more about feel and emotion than literal detail. DeRiso interprets the final verse as the boy singing after he has grown up and reflecting back on the advice he received long ago. The last lines of the song tweak famous lines from the traditional gospel song "On the Rock Where Moses Stood":

Rick Danko sings the lead vocal. Manuel plays drums on this song. Robertson plays a Merle Travis-sounding riff on guitar, and Garth Hudson and Manuel play organ and drums with a ragtime sound. Robertson has said that the guitar part was made up of combinations of notes that were not real chords. As a result, the melody didn't sound good when translated to piano, which is why Manuel, normally the group's pianist, moved to drums.Associated Press writer Mary Campbell heard an influence from Bob Dylan's music in "the way the tune moves forward."

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