What was Lil Wayne’s first number-one single?

Lil Wayne has released a lot of singles through the years. Of the more than a thousand tracks that he’s recorded, 286 have been released as singles—but surprisingly few have ever topped the charts in America.

The first Wayne single to chart at all was ‘Back That Azz Up’ by Juvenile, on which he was a featured artist. It reached as high as number 19 on the Billboard Hot 100, while also entering the top ten of the R&B/Hip-Hop Songs chart.

As a solo artist, Wayne released his first album, Tha Block Is Hot, towards the end of 1999. The title track, on which Juvenile and BG appeared, was a moderate success for the up-and-coming rapper, charting at number 72 on the Hot 100. It was a respectable showing for a new artist.

Wayne was prolific during the early 2000s, releasing several songs and albums that didn’t especially break into the mainstream. His biggest success of this period came with his appearance on the Destiny Child single ‘Soldier,’ which also featured TI. Released in November 2004, this song ultimately reached number three on the Hot 100. It marked Wayne’s first entry into the top ten.

But Wayne’s success wasn’t entirely down to his association with Destiny’s Child. He also released his fourth album, Tha Carter, around this period, with the record itself reaching number five on the Billboard 200 while also producing the successful single ‘Go DJ.’ This reached number 14 in America, his highest position for a solo track.

Tha Carter II dropped at the end of 2005, with the singles ‘Fireman’ and ‘Hustler Musik’ hitting numbers 32 and 87 respectively in the American singles charts. His collaborative album with Birdman, Like Father, Like Son, arrived the following year, and it did fairly well. But his biggest success was just on the horizon.

Tha Carter III was released in the summer of 2008, and it received a lot of praise and sold extremely well. It went straight to number one on the week of its release, selling a million copies within that first week and securing its position as one of America’s fastest-selling albums ever. It also produced a behemoth of a single.

‘Lollipop’ became Wayne’s first ever number one hit single, spending a total of five weeks at the top of the charts. It was eventually certified diamond by the Recording Industry Association of America (RIAA), meaning that it sold ten million units throughout the United States. It was, in short, a massive track.

Since that first chart-topping song, Wayne’s successes have been surprisingly few. Only two other tracks have ever reached number one since then, and they are both songs on which he was a featured artist. The first is Jay Sean’s ‘Down,’ released in 2009, and the other one is DJ Khaled’s ‘I’m The One’ from 2017, which also featured Justin Bieber, Quavo and Chance the Rapper.