Linked to the popularity of basketball in Puerto Rico, the recurrence of streetball (street basketball) has become intertwined with the practice of the sport in all of its levels. Taking influence from the grassroots connection of Nuyorican streetballers to the Baloncesto Superior Nacional, the practice is widespread in Puerto Rico, with impromptu games being a highly common occurrence for decades. Organized streetball gained momentum in the early 2000s and soon became involved with the local urban culture, especially the hip hop and reggaeton industries, giving origin to teams like Puerto Rico Streetball and the Puerto Rico Streetballers. Organizations based in Puerto Rico have played against foreign competition, with the results including the first win of an international team over the prominent AND1 Live Tour Team. Teams native to the archipelago are affiliated to the Street Basketball Association and FIBA's 3x3 basketball program.

Nuyorican streetball

Grassroots and the NY–BSN connection Initially, the Puerto Ricans arriving to New York as part of the great 1940s-50s migration were spurned by pre-established ethnic groups, which was also reflected when they attempted to practice basketball along players with these backgrounds. However, this soon changed when players developed in the courts of the local neighborhoods began distinguishing themselves due to their skills. The player credited with establishing a connection between New York basketball and Puerto Rico is Héctor Blondet, who began to practice it during his teens at Fort Green. At the Rucker Basketball Tournaments he played against players including Kareem Abdul-Jabbar, Nate "Tiny" Archibald, Dean Meminger and Connie Hawkins. Fernando Torres, who had experienced this discrimination was also among the first two players to break the "natives only" rule of the main professional league in Puerto Rico, the Baloncesto Superior Nacional along Blondet. The two had been recruited by the Capitanes de Arecibo, but the league refused to allow the signing until the matter was taken to court. Following his arrival to the BSN, Blondet established a bolder style of playing the sport, earning the nickname of "El Mago" (Spanish for "The Magician") due to his passing and overall abilities. It was Blondet who ultimately opened the doors to Nuyorican players with his unorthodox streetball-inspired skills. He soon joined the Puerto Rico men's national basketball team, becoming an Olympian. This created a surge and a group of Nuyorican players that later came to be known as "Los Tres Reyes" (Spanish for "The Three Kings"): Raymond Dalmau, Rúben Rodríguez and Neftalí Rivera.

Rubén Rodríguez quickly ascended in his native Brooklyn. His ability was noticed by coach Butch Purcell, who wanted him to play along Julius Erving at the Rucker. Rodríguez was brought to the BSN by the Vaqueros de Bayamón, a team that pioneered the tendency of bringing players from the New York diaspora to play in the archipelago. After gaining prominence in the BSN, he was among the first players to join the team following the end of the "Nuyorican barrier" in the late 1960s and early 1970s, which served as the spearhead to an influx of players to the program. The second member of the triad was Neftalí Rivera, who brought his own shot from the courts of New to the BSN. "El Tornillo" (Spanish for "The Corkscrew"), was a 360° 35-feet jumpshot that gained a fame as "the unblockable shot" in the BSN and was effectively used by Rivera, who established a pre-three-point line BSN record of 79 points in a single game that still stands. Rivera also joined the national team. The last member of "Los Tres Reyes" was Raymond Dalmau, who though born in Puerto Rico, was raised in the Grant Projects, learning to play from several places, including the Patterson Projects in the Bronx. He intentionally choose to stay in the BSN instead of joining the Utah Stars of the American Basketball Association in order to remain eligible to play in the national team, where he went on to become a star player. Dalmau played all of his professional career for the Piratas de Quebradillas. The success of Blondet and "Los Tres Reyes" in the BSN and national program had a significant impact in the Latin American communities in New York, particularly in the mostly Puerto Rican Spanish Harlem, which sparked a wave of interest in basketball. White Park became the main outdoor court for the diaspora, there pickup games featuring players from all ages became extremely popular, often counting with the participation of players such as Torres. All of the attention evolved into the Hispanic Superior Basketball, where Nuyorican streetballers were the main source of talent.

From this uproar emerged César Fantauzzi, who became the most prominent player in Spanish Harlem, where he earned his nickname "Spanish Doc" after capturing a jump shot attempt in midair. Fantauzzi entered the BSN with the Atléticos de San Germán earning a reputation as a power dunker and shot blocker, eventually following the footsteps of the other prominent Nuyoricans into the national basketball team, but his participation was brief for unrelated problems. Another player to gain fame during this time was Ángel "Ángelo" Cruz, who gained notoriety playing in the concrete courts of the Patterson Houses in Mott Haven. Known for his dribbling and dunking abilities, he was also recruited to play in the BSN, where he became part of the Indios de Canóvanas and made the national basketball team. Cruz was instrumental in bringing Andrés "Corky" Ortíz, a product of streetball raised on 117th off Madison, where he played against some of Rucker Park's legends, to the Gigantes de Carolina. Cruz was eventually joined in the Canovánas Indios by Bronx-native Héctor Olivencia, who had developed by playing pick up games in Rucker Park and the Webster Projects, who had entered the BSN when he was only 16 years old with the Criollos de Caguas. Born in Puerto Rico but raised in New York, Alfred "Butch" Lee became the most prominent Nuyorican player of the 1970s. He played constantly in the Rucker Park court, where he grew up watching the older players and getting involved in pick-ups, 5–2 and 1-on-1 full court games to hone his skills until he became a well rounded player. He was the first Puerto Rican selected in the NBA Draft and the first one to win an NBA championship ring (in 1980, as a member of the Lakers.) Lee joined the BSN in 1976 for the Cardenales de Río Piedras. who won the league championship that year. He was also the starting point guard in the Puerto Rico basketball team in the 1976 Montreal Olympics. Lee was a star at Marquette, leading that team to the NCAA championship in 1977. In 1978, he turned pro after being selected in the first round of the NBA draft by Atlanta. His NBA career was cut short by injuries, and he retired in 1981. At that point, he returned to the Puerto Rico basketball league where he played for a few more years, but due to the rules at the time, he couldn't play for the Puerto Rico national team because he had lost his amateur status.

Another Nuyorican raised in the Bronx was Georgie Torres, who began playing at the Mitchell Projects, gaining a fame as a sharpshooter that extended throughout his BSN and national team career. Torres was originally brought to the league when Olivencia discovered that he was Puerto Rican, but ended playing in 26 seasons throughout the 1980s and 1990s. Serving as opposite to these players was Wes Correa, born in Queens and who began to play in a makeshift basket made with a bicycle rim attached to a telephone post, before moving on to take on some of New York's best players. He was recruited to the Mets de Guaynabo by Earl Brown and four years later gained prominence in the national team by scoring 36 points in a game against the United States, which had Michael Jordan, Patrick Ewing and Chris Mullin in their lineup. Correa returned to New York in 2001 and played his first game at Rucker Park, where he has continued to perform gaining his nickname "Wil' Wild" Wes. The late 1980s brought James Carter to the BSN. From Queen and raised in the Baisley Projects in Southside Jamaica, he was told to tryout for the BSN while playing in a game in Brooklyn. Joining the Brujos de Guayama, Carter earned the nickname "El Presidente" and established himself in the national program.

The Urban Culture Renaissance In 1987, Bobbito García, also known as "Kool Love Bob", was playing a streetball game against Ray Díaz at Goat Park. Díaz, who had played in the BSN from 1982 to 1984 with the Piratas de Quebradillas, saw potential in the young García, recommending him to the office of the Capitanes de Arecibo. García gained experience in the BSN, becoming only the second player from his school to play professionally, and returned to play college. Upon returning to New York, García became instrumental in the streetball reinvention of the 1990s. García has also served as the announcer of CBS Sports-Red Bull's King of the Rock one-on-one tournament. In 1988 he began working for Def Jam Records, where he met DJ Stretch Armstrong beginning a DJ career that became tied to the Hip Hop scene in New York and led to international presentations as a club DJ. Gracía combined his interests in music and basketball, becoming the announcer and host of several streetball events, while also continuing to perform as a player. A published author and photographer, he became the co-founder of Bounce in 2003', a magazine which promotes streetball, urban fashion and professional basketball. He remained in the publication's staff until 2009, working on the creation of several special volumes along the regular issues. García has consistently continued to promote and practice streetball and basketball in general. Among his related work is the 2001 Nike Hip Hoop Tour, halftime shows for six universities and several NBA teams and coaching basketball programs in New York, the SEEDS Grow the Game Outreach Program and '10 Hoops for Hope. As a player, he has also been part of more than half a dozen teams, including some events that took place in Puerto Rico, such as the 2005 Playground Pros Revenge Tour. Behind the cameras, García is the co-director of the documentary Doin' It In The Park: Pick-Up Basketball, NY.