In 1983, the song peaked at number 2 in Australia. It originally peaked at number 44 on the Billboard Hot 100 in December 1982 but with its re-release, it peaked at number 12 in the US in July 1983, and at number 25 in the UK in January 1983 (reaching number 2 in the UK when re-released in January 1985, as part of a double A-side with "Little Red Corvette").
Following Prince's death, the song re-charted on the Billboard Hot 100 at number 41, later moving up to number 27, making it the fourth separate time the song had entered the Hot 100 and the third different decade in which the song re-charted (as after its two 1980s entries, it made the chart again on January 16, 1999 at number 40). As of April 30, 2016, it has sold 727,363 copies in the United States.
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.
Some music critics have suggested Phil Collins' 1985 song "Sussudio" sounds very similar to "1999". Collins confirmed this claim, and remembers listening to "1999" frequently while he was on tour with Genesis.
In January 1985, "1999" was released as a 12" single in the US 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 single peaked at number 2 in its second week of release.
"1999" was re-released in the UK and the US in late 1998 to accompany the song's namesake year. It was released on 12" vinyl with the same track listing as the original 12" single: the album version, along with "How Come U Don't Call Me Anymore?" and "D.M.S.R." A CD single was also issued with the same track listing, except the edit of "1999" was substituted for the album version. It was also re-released again towards the end of its namesake year. The original version re-charted within the Top 40 on the US Billboard Hot 100 in December 1998, becoming Prince's last top 40 hit before his death in 2016.
The video, directed by Bruce Gowers, was shot during the last week of rehearsals for the 1999 Tour. It depicts Prince and his band during a live performance. Just in time to take his part after Lisa Coleman, Jill Jones and Dez Dickerson, Prince appears on the stage from above, gliding down on a fireman's pole, wearing a glittery purple long coat.
Something went wrong with shooting Dez's lead vocal line and the footage was actually re-shot by a local camera crew the afternoon prior to the first show of the 1999 Tour in Chattanooga on November 11, 1982.