Pitbull was born of Cuban-American descent and grew up influenced both by the Cuban poet Jose Marti, whose works his parents made him memorize, and the Miami bass genre of hip hop music. He expressed interest in the West coast and East coast genres later in life. In 2002, Pitbull was featured on Lil Jon and the East Side Boyz' album Kings of Crunk and the soundtrack to the film 2 Fast 2 Furious the following year. In addition, Pitbull also released several mixtapes, composed of freestyles and remixes of popular rap music. Former 2 Live Crew leader Luther Campbell featured Pitbull in his single "Lollipop".
In 2004, Pitbull released his debut album M.I.A.M.I. (Money Is a Major Issue), with the lead single being "Culo" ("butt" in English; can be used as "ass" in context) produced by Lil Jon and the Diaz Brothers. It peaked at #32 on the Billboard Hot 100 chart and #11 on the Hot Rap Tracks chart. Other singles included "Dammit Man", "Back Up", "Toma", and "That's Nasty" (both featuring Lil Jon). He joined the Anger Management Tour, the 2005 hip-hop concert tour headlined by Eminem and 50 Cent. Pitbull also appeared on the Ying Yang Twins' single "Shake", which peaked at #41 on the Hot 100 and #12 on the rap chart, and Twista's "Hit the Floor" (#94 Hot 100, #20 Rap). Remix album Money Is Still a Major Issue was released in November 2005; it included new track "Everybody Get Up", a duet with hip-hop/R&B group Pretty Ricky.
TVT Records, Pitbull's label at the time, and Slip-N-Slide Records disputed over the release of Welcome to the 305, an unreleased album that Pitbull recorded with Slip-N-Slide in 2001. A judge in Miami made a decision allowing Slip-N-Slide to release the album, and a U.S. District Court judge affirmed the decision further. In March 2007, TVT was ordered to pay Slip-N-Slide $9.1 million for blocking the album release.
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. On Listennn... the Album, the debut album by Terror Squad member and Miami radio personality DJ Khaled, Pitbull performed on two singles: "Holla At Me" and "Born-n-Raised" alongside other Southern rappers.
El Mariel, Pitbull's second album, was released in October 2006. The title was in reference to the boat that transported Cuban refugees to Florida in the movie Scarface. Along with the usual party-oriented tracks, Pitbull also included politically-themed tracks in El Mariel. The album was released on October 31, 2006, and included singles "Bojangles", "Ay Chico (Lengua Afuera)", "Fuego", and duet with Puerto Rican singer Ken-Y, "Dime (Remix)". El Mariel topped the Billboard independent albums chart and peaked at #17 on the Billboard 200 and #2 on the rap chart.
Pitbull's third album, titled The Boatlift, was released in November 2007, spawned by the single "Secret Admirer" featuring Lloyd on the chorus. Earlier, Pitbull announced that this album would have a more gangsta rap edge than his earlier albums. Subsequent singles included "Go Girl" featuring Trina, and "The Anthem" featuring and produced Lil Jon, that song sampling the hook from the song "El Africano" by Wilfrido Vargas and the beat from the song "Calabria" by Rune RK. "Go Girl" peaked at #80 on the Billboard Hot 100 and #36 on the Hot Rap Tracks chart; "The Anthem" #36 on the Hot 100 and #11 on the Hot Rap Tracks.
His variety show, Pitbull's La Esquina, debuted May 2007 on the mun2 cable network. On December 21, 2007, Pitbull was arrested for drunk driving; he posted $1,000 on bail and pled not guilty. Pitbull also appeared on DJ Laz' "Move Shake Drop" and DJ Felli Fel's "Feel It".
For his latest album Rebelution, Pitbull released singles through Ultra Records: "Krazy" (featuring Lil Jon) and "I Know You Want Me (Calle Ocho)" after his former label TVT Records went out of business. "Krazy" peaked at #30 on the Hot 100 and #11 on the Hot Rap Tracks charts. "I Know You Want Me" peaked at #2 on the Hot 100 and peaked within the top ten spots of charts in the UK, Canada, France, Italy, and the Netherlands. He later signed with Polo Grounds Music through Sony Music and created his own label Mr. 305 Inc. Other singles included "Blanco" featuring Pharrell Williams of The Neptunes and "Hotel Room Service", the latter of which peaked at #15 on the Hot 100. On their second collaboration since "Go Girl", Pitbull appeared on the debut single of rapper David Rush (formerly Young Bo$$), "Shooting Star", also with Kevin Rudolf and LMFAO. An amateur video of Pitbull punching a disruptive audience member at a Colorado concert leaked on the Internet in late May 2009. Pitbull explained to MTV News that it was because the fan kept throwing cash around the stage. He has been tapped by the Miami Dolphins to work alongside T-Pain & Jimmy Buffett to release a new fight song for the dolphins.