Before releasing his debut album titled M.I.A.M.I (Money is A Major Issue) in August 2004, Pitbull was featured on Lil Jon's Kings of Crunk (2002) album and the 2 Fast 2 Furious soundtrack (2003). His breakout hit was the Lil Jon collabo "Culo" produced by Lil Jon & The Diaz Brothers. In addition, Pitbull has also released several mixtapes, the most recent being Unleashed Volume 5, which are mostly composed of freestyles and remixes of popular rap music. Both thematically and musically, the 25-year-old is seen as a modern-day equivalent of earlier Miami rappers such as the 2 Live Crew and Afro-Rican. 

It was in fact former 2 Live Crew leader Luther Campbell who gave the up and coming rapper his first chance to shine. Apart from Crunk, his album shows clear influences from both Miami bass and freestyle. In addition to his musical work, Pitbull has also been featured in The Source expressing his stance on Fidel Castro and he was also part of their Unsigned Hype Section. He contributed to an essay published in the New York Post that criticized Che Guevara's iconization in clothing and other areas. In video games, Pitbull's hit single "Dammit Man" produced by Jim Jonsin is featured in Midnight Club 3: DUB Edition, and he also plays himself in the upcoming video game based on the 1980's Scarface. His super hit "Toma" is featured in WWE Day of Reckoning 2. Also, an album cut, "Back Up" produced by The Diaz Brothers, is featured on the EA game Fight Night: Round 2. In late 2005 he re-released "M.I.A.M.I." as a separate charting entry, whilst his "Welcome to the 305" mixtape was released. In January 2006 he guest-starred in UPN's South Beach. Also in 2006 he Recorded "Nuestro Himno" in collaboration with Wyclef Jean, Carlos Ponce, and Olga Tañón.
The first single from El Mariel has been released, entitled "Bojangles". The album, slated for an October 31st release, will feature guest artists Lil Jon, Ken-Y of Rakim y Ken-Y, Rick Ross, Bun B and the Ying Yang Twins. El Mariel will lead up to Pitbull's 2007 release of an all-Spanish album entitled "Armando", which will have an Afro-Cuban feel.

Pitbull has a global music publishing deal with BMG Music Publishing. On the evening of July 31st, 2006, when Cuban President Fidel Castro announced that he was transferring his duties to his brother Raúl Castro, Pitbull jumped into the studio at 11:00PM to write the Ya Se Acabo (which means 'it is over') single. Stating the verse 'hasta luego' (which means 'see you later') during the duration of the song. The song is currently being played widely on Miami radio stations, most noteably Power 96.

Pitbull has contributed alot to the Reggaeton music movement. He has worked alongside with Zion Y Lennox in the song Jump & Spread Out featuring Miri Ben-Ari. He also participated in Daddy Yankee's Gasolina remix featuring N.O.R.E.. He was also featured in Yaga & Mackie Rank's Muevete hot Reggaeton single.