The single reached a new peak of number 2 on the Billboard Hot 100 on April 17, 2008, making it his highest-charting single as both a lead artist or as a featured performer. The following week, it reached a new peak of number 7 on the Hot 100.

His previous highest-charting position as a lead artist was with ' Go D.J.', which peaked at number 14 in 2004. 'Lollipop' jumped 76 spots from number 85 to number 9 on the Maissue of the Billboard Hot 100, becoming Lil' Wayne's highest-charting single as a lead artist, along with being his first top ten hit on the chart as a lead artist. Static Major died unexpectedly during a medical procedure on February 25, 2008, sixteen days before the song was released. The song won a Grammy Award in February 2009 for Best Rap Song. The final frame of the video is a picture of Static praying with the words 'In memory of Stephen 'Static Major' Garrett'. Jim Jonsin, Tyga, Birdman and Mack 10 make cameos in the video.

The video is the most-viewed video on Music Choice's video on demand service. The limousine that Wayne and Static get into at the start of the video is based on an International XT pickup truck. It also reached number one on TRL in April on MTV. The video premiered via BET's Access Granted on March 12, 2008. The music video was directed by Gil Green and filmed in Las Vegas at Gavin Maloof's residence on December 31, 2007. Lil Wayne in the music video for 'Lollipop.' With 9.1 million copies sold as of January 2009, 'Lollipop' was named 2008's best-selling digital single worldwide by IFPI. The song was ranked at number five on Rolling Stone 's list of the 100 Best Songs of 2008. The song reached number one on the 2008 issue of Notarized by BET. The single was certified 5x Platinum by the RIAA for selling five million units in the United States and was ranked the number one hip hop song of 2008 by MTV. Static Major died just over two weeks before the release of the song, making the song the eighth to hit number one after the death of a credited artist. 'Lollipop' is Lil Wayne and Static Major's most successful single to date, spending five non-consecutive weeks atop the Billboard Hot 100 chart. The song was released digitally on March 13, 2008. It heavily utilizes the Auto-Tune vocal effect. The track posthumously features vocals from American singer Static Major and was produced by Deezle and Jim Jonsin. ' Lollipop' is a song by American rapper Lil Wayne, issued as the lead single from his sixth studio album, Tha Carter III. Single by Lil Wayne featuring Static Major

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