"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. and is the single most downloaded ringtone 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.

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 Grantedon 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.

The song won a Grammy Award in February 2009 for "Best Rap Song."

"Lollipop" jumped 76 spots from number 85 to 9 on the March 28, 2008 issue of the BillboardHot 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. His previous highest chart position as a lead artist was with "Go DJ", which peaked at #14 in 2004. The following week it reached a new peak of #7 on the Hot 100. The single reached a new peak of #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. (Lil Wayne was a featured artist for Destiny's Child's #3 (Hot 100) hit, "Soldier".) For the week of May 3, 2008, "Lollipop" reached the #1 spot on the Hot 100, his first #1 on the chart. The same week, it was #1 on TRL. It has become Wayne's first number one on the Hot R&B/Hip-Hop Songs chart and the Hot Rap Tracks chart. On the Hot R&B/Hip-Hop Songs chart, it is the first rap song to reach #1 since Ludacris' "Money Maker" in 2006. After one week, it slipped away from #1 on the Hot 100, but after a three-week rest the song returned, making it the song with the longest break in between peaking the Hot 100 since Usher's "U Got It Bad."

The week after the release, Wayne earned the biggest add week that a hip-hop artist received at Rhythm Crossover and the biggest for any artist at Urban Radio, including Beyoncé and. Mariah Carey. The song became the #1 most added and greatest gainer at both radio formats with a total of 138 adds. "Lollipop" has become a crossover hit on mainstream radio, as it became his first top 40 hit as a lead artist, entering at #36, and has so far peaked at #5. It is his first top ten on the Pop 100, where it has reached #2. Z100 added "Lollipop" as of April 17, 2008, making it his first add on the station as a solo artist. It returned to #1 on the Billboard Hot 100 for the second time on the 22 of May 2008.

The song has become a top ten success in Canada, so far peaking at #10 as of May 29, 2008, and his most successful song in the UK, where it has reached #26 on downloads alone. It reached #5 on the New Zealand charts and rose to #3 the next week.

The official remix features Static Major & Kanye West. Other remixes feature Young Jeezy, Gorilla Zoe, Ace Hood, Kurupt, V.I.C., Nicki Minaj, Framing Hanley, Tekitek, & Khia, who made a popular female version of the song .

The alternative/modern rock band Framing Hanley covered the song as a bonus track on their album The Moment. It uses a slight bit of talkbox, but replaces almost all the other sound with electric guitar, and features a hard rock version of the lyrics sung by the band.

Tha Block Is Hot · Lights Out · 500 Degreez · Tha Carter · Tha Carter II · Tha Carter III · Rebirth · Tha Carter IV

Like Father, Like Son · We Are Young Money · I Can't Feel My Face

The Prefix · Suffix · Dedication · Dedication 2 · Da Drought 3 · The Leak · Dedication 3 · No Ceilings

I Am Music Tour · America's Most Wanted Tour

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