Which single won the 2009 Grammy award for Best Rap Song?

The single that won the 2009 Grammy Award for Best Rap Song was “Lollipop” by Lil Wayne featuring Static Major.

The award was presented at the 51st Annual Grammy Awards on February 8, 2009. “Lollipop” was recognized in Best Rap Song, a songwriter-focused category honoring the composition’s music and lyrics. The credited songwriters included Lil Wayne, Static Major, Darius “Deezle” Harrison, James Scheffer and Rex Zamor.

Released in 2008, “Lollipop” became Lil Wayne’s first No. 1 single on the Billboard Hot 100 and one of the defining hits from his album Tha Carter III. Static Major, who provided the featured vocals, died shortly before the song’s release, making its later success and Grammy recognition especially significant.

A common mix-up is “Swagga Like Us,” which won the Grammy for Best Rap Performance by a Duo or Group at the same ceremony. Lil Wayne also won Best Rap Album for Tha Carter III and Best Rap Solo Performance for “A Milli,” giving him four Grammy wins that night.