"Daysleeper" was the first single to be released by R.E.M. from the band's eleventh studio album Up, and the first single to be released by the band since the departure of drummer Bill Berry.

Sleep and dreams have often played an important part in R.E.M. lyrics, for example "Get Up" and "I Don't Sleep, I Dream".

Sung from the point of view of a nightworker corresponding with far eastern colleagues, the song focuses on the disorientation of time and "circadian rhythm" in such a lifestyle, leading to despair and loss of identity. The "Bull," and the "Bear" mentioned as "marking their territory" refer not to stock market trends, but to the United States (the bull) and China (the bear), imagined as two giant urinating animals dividing up the world between themselves.

During R.E.M.'s performance for VH1 Storytellers, Stipe explained the background to the song: "I was in New York, putting together a book of haikus that I worked on with several dear friends of mine over the course of a year. And I was walking down the steps of this building, it was probably four o’clock in the afternoon and I saw — they didn’t have an elevator, what’s that called? Tenement building. Is that right? [shouts from the audience] A walk-up. Sorry! [laughs] Native New Yorkers. I’m stomping down the stairs, it’s 4 o’clock in the afternoon and I come to a door — it’s apartment 3d or something — and there's a sign on it that says "Daysleeper," and I walked a lot more carefully, quietly down the steps, thinking about that poor person who's trying to sleep, and me and my big old boots interrupting her sleep. So I wrote this song about a daysleeper that's working an 11-7 shift and how furious the balance is between the life that you live and the work that you have to do in order to support the life that you live."

The video, shot at Broadway Studios in the Astoria district of New York City in September 1998, Q, October 1998 was filmed in stop-frame photography to get what Stipe called a "really druggy, really great look." Q, October 1998 It features Stipe as the office worker who goes to work at night. All three band members then wear pajamas and bed socks, while failing to get to sleep during the day. The video was directed by the Icelandic Snorri brothers. "I think it's about the sort of alien nature of a night shift," explained Mike Mills. "The weird lighting, the fluorescent lights that you find and the isolation of working the graveyard shift - how it screws up your sleep patterns and that sort of thing, and I think that's the main image we're trying to get across." Q, October 1998