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A promotional single entitled "Birthday", featuring Rick Ross, was his first significant release.
He made his debut guest appearance with the song "Bitch I'm From Dade County" on DJ Khaled's album We the Best (2007), which also features Trick Daddy, Trina, Rick Ross, Brisco, C-Ride, and Dre.
On December 9, he performed "Let it Roll" and "Wild Ones" at the 2012 edition of WWE's Tribute to the Troops. The song became his tenth top 10 hit in the United States, peaking at number 8 in the Billboard Hot 100 chart and at number 3 in the US Top 100 chart on i Tunes. On March 24, 2016, he released the promotional single "Who's With Me".
His 2007 breakout single "Low" was number one for 10 weeks in the United States and broke the record for digital download sales at the time of its release. Early on in his career one of his sisters, Julia died due to bronchitis.
Flo Rida's debut studio album, 2008's Mail on Sunday, reached number four in the US. Her death greatly affected Dillard and his career, with him telling MTV "I was very close to her, and I told myself that I was going to do this for my sister." They developed a long lasting friendship; Flo Rida considers this period as his schooling.
The song broke a record for the most digital one week sales in the US, with 636,000, beating the previous record he had set himself with "Low". "Jump", featuring singer Nelly Furtado, was the third official single and was released on July 27, 2009 in the UK, and July 28, 2009 worldwide.
The second official single was "Sugar", which featured R&B singer Wynter Gordon. "Be on You", featuring singer Ne-Yo, was the album's fourth official single, released on October 6, 2009.