For the week of May 3, 2008, "Lollipop" reached the number-one spot on the Hot 100, his first number one on the chart. It is also Wayne's first number one on the Hot R&B/Hip-Hop Songs chart and the Hot Rap Tracks chart.

"Lollipop" is a pop song written by Julius Dixson and Beverly Ross in 1958. It was first recorded by the duo Ronald & Ruby, with Ross performing as "Ruby." It was covered more successfully by The Chordettes whose version reached No. 2 in the US, and The Mudlarks in the UK.

With “Lollipop,” Wayne crafted one of the biggest crossover singles ever, establishing the complete hip-hop domination he'd been talking about for years. If there were still any doubters, “A Milli” proved not only that he could play in the pop lane, but that he could out-rap just about anyone.

Mika wrote the song as a message to his younger sister, warning her not to have sex too soon as it would "mean something very different to guys than it would to her".