Big Punisher: 1971-2000: Rapper

In 1989 Big Pun, who then went by the moniker Big Moon Dog, formed the Full-A-Clips Crew with fellow Latin rappers Triple Seis and Cuban Link. Popular Bronx producer and fellow Puerto Rican rapper Joseph Cartagena, a.k.a. Fat Joe, singled Big Pun out in 1995, after hearing the hefty rapper rhyme. "I knew he was one of the great ones," Fat Joe told Aliza Valdes-Rodriguez of the Los Angeles Times. "I was totally impressed by his rapping, the delivery with the tongue-twisting metaphors."

Big Pun and Fat Joe developed a close relationship; Big Pun would later refer to Fat Joe, who weighed in at 300 pounds himself, as his "twin." The two would later become heroes of New York's Puerto Rican community; they each rode their own floats in the 1998 and 1999 Puerto Rican Day parades in New York City. Fat Joe immediately recognized Pun's extraordinary rhyming and lyrical skills, and invited him to record a cameo on Fat Joe's song "Watch Out." Renamed Big Punisher, the rapper became part of the Terror Squad, a crew made up of the Latin rappers associated with Fat Joe. Soon after his recording debut, Fat Joe negotiated Pun's contract with New York's Loud Records. Pun was one of the few newcomers included on The Mix Tape Vol. 1, a compilation put together by influential New York DJ Funkmaster Flex.

Pun released the single "I'm Not a Player" in the winter of 1997, and his debut full-length album, Capital Punishment, followed a few months later. The album featured cameos by some of the hottest names in hip hop at the time: Wyclef Jean on the reggae-flavored song "Caribbean Connection," Black Thought from the Roots on "Super Lyrical," and Wu-Tang Clan's Inspectah Deck and Prodigy from Mobb Deep on "Tres Leches." Big Pun laments mistreatment from an ex-lover in the ballad "Punish Me" and, on the album's closer, "Parental Discretion," featuring Busta Rhymes, Pun let loose one of the tongue-twisting, run-on rhymes he was famous for: "I recollect when I was just a boy eating Chips Ahoy/wasn't allowed to raise my voice/now I'm making noise." The single "Still Not a Player" pushed the album to platinum status within a few months of its release.

Pun was known for his remarkable breath control and ability to squeeze out a seemingly endless stream of rhymes in one breath. He also was known for his lyrical humor and ability to string together complex and tongue-twisting rhymes. "Big Pun possessed a lyrical gift of incessant breath control and a knockout punch with the rhymes," according to his biography on the Loud Records' website. While other rappers strung together rhymes about flashy riches, disrespecting women, and the violence and crime of ghetto street life, Big Pun described his style as "sophisticated hard-core," according to Jon Pareles of the New York Times. "I'm talking about everyday life," Big Pun said in an MTV interview, "losing your job, losing a loved one, stress, happiness, whatever." The rapper was hardly relating the struggles of the average working man, however. His "lyrical stance fitted the late 1990s sexual braggadocio and drugs and gun culture which attracted teenage America to the hip-hop world," according to Pierre Perrone in the London Independent.