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"Lollipop" is the first single from Lil Wayne's sixth studio album, Tha Carter III. The track features the late R&B artist Static Major and is produced by Deezle and Jim Jonsin. The song was released digitally on March 13, 2008. The song features Auto-Tune vocals. The song is Lil Wayne's & Static Major's most successful to date, spending 5 non-consecutive weeks atop the Billboard Hot 100 chart. Static Major died two weeks before the release of the song. There are various versions of the song. The single was certified 5x Platinum by the RIAA and was ranked the #7 Hip-Hop song of 2008 by MTV. The song reached #1 on the 2008 issue of Notarized by BET. This song was #5 on Rolling Stone's list of the 100 Best Songs of 2008. It is the single most downloaded song of the 2000s.

The song was originally for Danity Kane, but their A&R did not pick it up. Jonsin gave the beat to Static Major, who passed it on to Lil Wayne.

Originally it was rumored to be called: Lollipop Rocks..

The music video was directed by Gil Green and filmed in Las Vegas at Gavin Maloof's residence in the Southern Highlands Golf Club. The video premiered via BET's Access Granted on March 12, 2008. It also reached no. 1 on TRL in April on MTV

The video is the most-viewed video on Music Choice's video on demand service.

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