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"1999" is one of Prince's best-known songs, and a defining moment in his rise to superstar status. The apocalyptic yet upbeat party anthem saw chart success in 1983, peaking at #12 in the US and #25 in the UK (reaching #2 in the UK when re-released in 1985). The album version of the song starts with a slowed-down voice, reassuring the listener "Don't worry, I won't hurt you. I only want you to have some fun." Prince shares lead vocals on the track with members of his band The Revolution, namely Dez Dickerson, Lisa Coleman and Jill Jones. Originally conceived to be a three-part harmony, it was later decided to separate out the voices that started each verse. The verse melody was reused by Prince (writing under the name "Christopher") in the song "Manic Monday," originally written for Apollonia 6's eponymous 1984 album, but withdrawn at the last minute and eventually given to The Bangles. The synth chords inspired Phil Collins' song "Sussudio" as well as Marillion's "Incommunicado".

The B-side, the piano ballad "How Come U Don't Call Me Anymore?", became a fan favorite. It was covered first by Stephanie Mills, then by Alicia Keys and performed by Canadian Idol winner Eva Avila.

In 1985, "1999" was released as a 12" single in the U.S. with "Little Red Corvette" as the B-side, and "How Come U Don't Call Me Anymore?"/"D.M.S.R." in the UK.

The song was re-recorded at the end of 1998 with the New Power Generation, reusing portions of the original recording, and was released the following year as 1999: The New Master. This new version was generally panned by critics; however, it did re-chart at #40 on the US chart, becoming Prince's last top forty hit to date. It was again re-released in December, 1999, and re-charted at #56.

On New Year's Eve 1999, Prince (his stage name at that time still being an unpronounceable symbol) held a concert entitled Rave Un2 the Year 2000 at his Paisley Park Studios Soundstage, and he later vowed never to play it again. However, in August 2007, as part of his Earth Tour, he reintroduced the song to his set after an absence of eight years.

Rolling Stone ranked the song #212 on their list of the 500 Greatest Songs of All Time.

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