"Lollipop" is the first single off of American rapper Lil Wayne's sixth studio album Tha Carter III. The song also features American singer Static Major. The song was released on March 13, 2008. The song was able to make it to #1 on the Billboard Hot 100, spending five weeks there. It was also certified 5× Platinum by the Recording Industry Association of America (RIAA). Static Major died two weeks before the song was released.
The song won Best Rap Song at the 51st Annual Grammy Awards. Rolling Stone ranked the song #5 on their list of the 100 Best Songs of 2008.
The song is about a woman performing oral sex on Wayne with lyrics like "she licked me like a lollipop." The music video shows Lil Wayne and Static Major riding and partying in a giant limousine down the Las Vegas Strip. The video is dedicated to Static Major.