This is the first single from American rapper Soulja Boy Tell 'Em's third album, The DeAndre Way. G5Kids Young Shay & Murph produced the song.
There have been accusations that Soulja Boy stole the song from Next Generation Boyz, who released a song also titled "Pretty Boy Swag" on July 28, 2009. After Soulja Boy's recording came out, the Next Generation Boyz put out a diss, stating that rap superstar had jacked their tune. Soulja Boy denies the accusations.
The official remix features rapper Gucci Mane and R&B singer Ciara.
Soulja Boy told Billboard magazine how this hard-hitting DeAndre Way lead single and its corresponding music video helped alert his fans that he was maturing as an artist. "I had to give them a visual on where I wanted to go with this album," he said. "'Pretty Boy Swag' was a free style that I did in the studio… I had to update them on my appearance, on my style, on everything, and that was the perfect way to go."