# Lollipop (Lil Wayne song)
**"Lollipop"** is a 2008 song by the American rapper [Lil Wayne](https://www.edgepedia.org/lil-wayne) featuring the singer and producer [Static Major](https://www.edgepedia.org/static-major), released as a single from the album *Tha Carter III*. Produced by Jim Jonsin and Deezle, it became Lil Wayne's first number-one hit, won the Grammy Award for Best Rap Song in 2009, and was later certified Diamond by the [Recording Industry Association of America](https://www.edgepedia.org/recording-industry-association-of-america), the first Diamond certification of his career[1](https://digital.abcaudio.com/news/lil-waynes-lollipop-officially-certified-diamond) • [2](https://www.musicvf.com/song.php?id=82604&title=Lollipop+by+Lil+Wayne) • [3](https://ratemydick.ai/music/songs/lil-wayne-lollipop).
| Key fact | Detail |
|---|---|
| Artist / featured guest | Lil Wayne, posthumously featuring Static Major[4](https://lilwayne.fandom.com/wiki/Lollipop) |
| Release | 2008; one of 16 tracks on *Tha Carter III*[1](https://digital.abcaudio.com/news/lil-waynes-lollipop-officially-certified-diamond) |
| Production | Jim Jonsin and Deezle[4](https://lilwayne.fandom.com/wiki/Lollipop) |
| Writers credited | Furious, Sean Garrett, James Scheffer, Lil Wayne, and Rex Zamor[5](https://www.allmusic.com/album/lollipop-mw0001676778) |
| Certification | RIAA Diamond, 10 million sales and streaming equivalents; Lil Wayne's first Diamond song[1](https://digital.abcaudio.com/news/lil-waynes-lollipop-officially-certified-diamond) |
| Award | Grammy Award for Best Rap Song, 2009[2](https://www.musicvf.com/song.php?id=82604&title=Lollipop+by+Lil+Wayne) |
| Streaming | About 843 million plays on Spotify as tracked by the chart aggregator kworb[6](https://www.kworb.net/spotify/artist/55Aa2cqylxrFIXC767Z865_songs.html) |
## Creation of the song
The beat began as a rejected track. Jim Jonsin, a producer who moved between rap and R&B work, made it while working on [Danity Kane](https://www.edgepedia.org/danity-kane)'s project at Circle House Studio; the group passed on it, and he brought it to Static Major, who loved it and began writing to it immediately[7](https://www.xxlmag.com/lil-waynes-tha-carter-iii-recounted-through-oral-history/) • [8](https://youknowigotsoul.com/interview-producer-jim-jonsin-going-for-that-number-one-spot-with-rebel-rock-movement). A later account attributes the track instead to a session connected with Dem Franchize Boyz, in which Static came to town and was played a song intended for that group[9](https://hiphopwired.com/3001941/lil-wayne-lollipop-dem-franchize-boyz/); the two accounts describe different routes to the same recording.
**Static Major's role was decisive.** In Jonsin's recollection, Static wrote the top-line melody, and [Pleasure P](https://www.edgepedia.org/pleasure-p), then of [Pretty Ricky](https://www.edgepedia.org/pretty-ricky), helped out with a couple of things; Jonsin sampled pieces of Static's vocals, including the "Call me" line, on his drum machine[7](https://www.xxlmag.com/lil-waynes-tha-carter-iii-recounted-through-oral-history/). Deezle, who co-produced the record, described building the song with Static in a separate session: "It was his concept, and we went through that whole song together because he knew how he wanted it to feel at certain points. So, I made adjustments, and he did what he does best. He made up all the vocals on the spot, man. The whole song. It was recorded in about 30 minutes."[7](https://www.xxlmag.com/lil-waynes-tha-carter-iii-recounted-through-oral-history/)
From there, either Static or Pleasure P brought the track to Lil Wayne, who cut the chorus and verses over a song whose B section and bridge were already written; Jonsin was not present for Wayne's recording[7](https://www.xxlmag.com/lil-waynes-tha-carter-iii-recounted-through-oral-history/). The Lil Wayne Wiki account adds that Static, at Pleasure P's suggestion, reached out to Wayne in hopes of a collaboration[4](https://lilwayne.fandom.com/wiki/Lollipop). Billboard reported in February 2008 that the official single, produced by Deezle and featuring Static, would be serviced to radio shortly, with Jim Jonsin, the [Alchemist](https://www.edgepedia.org/alchemist), and Cool and Dre also contributing production to the album[10](https://www.worldradiohistory.com/Archive-All-Music/Billboard/00s/2008/BB-2008-02-09.pdf).
## Static Major's death and the feature
Static Major, a writer and producer known for his work with Jay-Z and Aaliyah, died before "Lollipop" was released; the single arrived with his vocal work intact, making it a posthumous feature[11](https://www.orlandoweekly.com/music/the-water-cooler-man-2257072/) • [4](https://lilwayne.fandom.com/wiki/Lollipop). An AllHipHop remembrance recalls the shock of his death and the record with Lil Wayne dropping afterward[12](https://allhiphop.com/mobile/remembering-static-major/).
Jonsin later described Static as one of the most amazing writers he had ever worked with and a mentor who taught him the importance of strong melodic writing; he called Static the first person he worked with on R&B records and "one of the greatest of all time"[8](https://youknowigotsoul.com/interview-producer-jim-jonsin-going-for-that-number-one-spot-with-rebel-rock-movement).
## Credit disputes
In 2023, Pleasure P, the former Pretty Ricky singer, said that he had co-written "Lollipop" with Static Major, originally for his own album, and had never received credit, demanding recognition and a share of the $28 million he said the song had earned[13](https://hiphopdx.com/news/pleasure-p-co-wrote-lil-wayne-lollipop-never-got-credit/?next_ids%5B0%5D=867944) • [14](https://www.complex.com/music/a/alex-ocho/pleasure-p-28-million-lil-wayne-lollipop). Jonsin's own 2008 account to HipHopDX mentioned Pleasure P as present while Static was working on the track, though he did not describe him as a writer[13](https://hiphopdx.com/news/pleasure-p-co-wrote-lil-wayne-lollipop-never-got-credit/?next_ids%5B0%5D=867944). The song's published credits list Furious, Sean Garrett, James Scheffer, Lil Wayne, and Rex Zamor as composers, with Jonsin as producer and Darius "Deezle" Harrison on drums[5](https://www.allmusic.com/album/lollipop-mw0001676778).
## Commercial and critical standing
The single became the biggest record of Lil Wayne's career to that point. It was his first number-one hit and the biggest song from *Tha Carter III*, the album that sold over a million copies in its first week[3](https://ratemydick.ai/music/songs/lil-wayne-lollipop) • [7](https://www.xxlmag.com/lil-waynes-tha-carter-iii-recounted-through-oral-history/). In 2022, the RIAA certified it Diamond for 10 million sales and streaming equivalents, his first certification at that level[1](https://digital.abcaudio.com/news/lil-waynes-lollipop-officially-certified-diamond). It also won the Grammy Award for Best Rap Song at the 2009 ceremony; "Lollipop" and "A Milli" both won Grammy awards that year[2](https://www.musicvf.com/song.php?id=82604&title=Lollipop+by+Lil+Wayne) • [15](https://openscholar.uga.edu/record/10001/files/dupriest_benjamin_m_201305_ma.pdf). The Associated Press later counted "Lollipop" among the massive hits of a rapper with five Grammy wins who helped ignite the careers of [Drake](https://www.edgepedia.org/drake-musician), Nicki Minaj, and Tyga[16](https://apnews.com/article/a1eea3f07f921d3ff475977651214a5d).
**Sound and subject.** The song is a slow, Auto-Tuned request that a woman treat him like a "lollipop," built on an electronic beat[3](https://ratemydick.ai/music/songs/lil-wayne-lollipop). Its lyrics are built on an extended double entendre describing a sexual encounter; Tricia Rose's *The Hip Hop Wars* notes that nearly all of the lyrics detail sex acts between Lil Wayne and a woman he hooks up with at a club[17](https://womeninmusic.voices.wooster.edu/wp-content/uploads/sites/123/2017/12/Rose-Hip-Hop-Wars-113-31-149-65.pdf). AllMusic classifies the single as Southern Rap and [Dirty South](https://www.edgepedia.org/dirty-south), with a main version running 4:10 and a second version at 5:02[5](https://www.allmusic.com/album/lollipop-mw0001676778).
## References
1. [Lil Wayne's "Lollipop" is officially certified Diamond, ABC Audio Digital Syndication](https://digital.abcaudio.com/news/lil-waynes-lollipop-officially-certified-diamond)
2. [Lollipop (song by Lil Wayne), Music VF](https://www.musicvf.com/song.php?id=82604&title=Lollipop+by+Lil+Wayne)
3. [Lollipop Meaning: What Lil Wayne's Song Is Really About, RateMyDick.ai](https://ratemydick.ai/music/songs/lil-wayne-lollipop)
4. [Lollipop, Lil Wayne Wiki (Fandom)](https://lilwayne.fandom.com/wiki/Lollipop)
5. [Lil Wayne: Lollipop Tracks & Reviews, AllMusic](https://www.allmusic.com/album/lollipop-mw0001676778)
6. [Lil Wayne - Spotify Top Songs, kworb](https://www.kworb.net/spotify/artist/55Aa2cqylxrFIXC767Z865_songs.html)
7. [Lil Wayne's 'Tha Carter III' Recounted Through Oral History For 5th Anniversary, XXL](https://www.xxlmag.com/lil-waynes-tha-carter-iii-recounted-through-oral-history/)
8. [Producer Jim Jonsin - Going For That Number One Spot With Rebel Rock Movement (Exclusive Interview), YouKnowIGotSoul](https://youknowigotsoul.com/interview-producer-jim-jonsin-going-for-that-number-one-spot-with-rebel-rock-movement)
9. [Lil Wayne's 'Lollipop' Was Originally Made For Dem Franchize Boyz, HipHopWired](https://hiphopwired.com/3001941/lil-wayne-lollipop-dem-franchize-boyz/)
10. [ON THE UPSWING, Billboard, February 9, 2008 (worldradiohistory archive)](https://www.worldradiohistory.com/Archive-All-Music/Billboard/00s/2008/BB-2008-02-09.pdf)
11. [THE WATER COOLER MAN, Orlando Weekly](https://www.orlandoweekly.com/music/the-water-cooler-man-2257072/)
12. [EXCLUSIVE: Remembering "Lollipop" Producer Static Major, AllHipHop](https://allhiphop.com/mobile/remembering-static-major/)
13. [Pleasure P Says He Co-Wrote Lil Wayne's 'Lollipop' & Never Got Credit, HipHopDX](https://hiphopdx.com/news/pleasure-p-co-wrote-lil-wayne-lollipop-never-got-credit/?next_ids%5B0%5D=867944)
14. [Pleasure P Says He's Owed $28M for Co-writing Lil Wayne's "Lollipop", Complex](https://www.complex.com/music/a/alex-ocho/pleasure-p-28-million-lil-wayne-lollipop)
15. [Complicating the Complex: Lil Wayne and..., UGA thesis](https://openscholar.uga.edu/record/10001/files/dupriest_benjamin_m_201305_ma.pdf)
16. [Dr. Dre, Missy, Lil Wayne to be honored at pre-Grammy event, AP News](https://apnews.com/article/a1eea3f07f921d3ff475977651214a5d)
17. [Tricia Rose, The Hip Hop Wars (excerpt), Women in Music, Wooster](https://womeninmusic.voices.wooster.edu/wp-content/uploads/sites/123/2017/12/Rose-Hip-Hop-Wars-113-31-149-65.pdf)
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*Topic: Encyclopedia › Arts and culture › Music › Musical works and recordings › Compositions and songs › Pop, rock, and metal songs › Hip-hop songs › 2000s hip-hop songs*
*Initially written Sep 17, 2026 · Reviewed: Sep 30, 2026; Oct 25, 2026 · Edited: Sep 30, 2026; Oct 25, 2026 · Last review: Oct 25, 2026*
*Copyright 2026 EdgeChat AI, a subsidiary of Biostate AI.*
License: Edgepedia Community License 1.0, https://www.edgepedia.org/edgepedia/license