"I Should Be Sleeping" is a song written by Shaye Smith and Lisa Drew, and recorded by Canadian country music group Emerson Drive. It was released in October 2001 as their first single from their debut self-titled album, Emerson Drive. The song reached the Top 5 on the U.S. Billboard Hot Country Songs chart, reaching a peak of number 4. It also peaked at number 35 on the U.S. Billboard Hot 100, making it their first crossover hit.

The narrator states that he should be sleeping instead of dreaming about his significant other.

The music video was directed by Thom Oliphant and premiered in late 2001.

"I Should Be Sleeping" debuted at number 57 on the U.S. Billboard Hot Country Singles & Tracks for the chart week of November 10, 2001.

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