Artists like Jowell Y Randy

Wisin & Yandel were a Puerto Rican reggaeton duo consisting of Wisin and Yandel. They started their career in 1998 and stayed together until 2023, winning several awards including a Grammy Award in 2009. They became the first reggaeton artists to win one. In late 2013, they announced they would take a pause in their career as a duo, after their Líderes Tour. In a 2014 interview with People en Español, Yandel confirmed that the group would not be disbanding. In February 2018, following a five-year hiatus, the duo announced they would be reuniting, and were set to embark on a world tour, as well as release new music. They sold over 15 million records.

R.K.M & Ken-Y is a Puerto Rican reggaeton duo formed in 2003 by José Nieves (R.K.M) and Kenny Vázquez (Ken-Y). The artists are renowned in the Latin music world for being the first to successfully fuse mainstream pop music with the reggaeton street rhythms of Puerto Rico and expose the style to a wide international audience. The sound introduced by R.K.M & Ken-Y would go on to inspire the pop reggaeton songs of successful acts such as CNCO, J Balvin, and Maluma. The duo had a very successful career with the Spanish-speaking audience of Latin America, the United States, and Spain until their separation in 2013. In June 2017, the duo announced their official return by Pina Records. In mid-2021 the Duo confirmed that they are on hiatus and are currently working on their solo projects.

Trébol Clan is a Puerto Rican reggaeton musical group, introduced in the genre by DJ Joe. Formed by Hector Pagan "Periquito/Trebol", Omar "Plomo" and Berto "El Original", Trébol Clan has been featured in Don Omar's The Last Don and Los Bandoleros, Luny Tunes's Mas Flow 2, and have released one CD in the genre named Los Bacatranes. When they had their label, they released the mixtape Los Reyes de la Lenta: The Comeback (2008).

Julio Voltio is a Puerto Rican former rapper. An early pioneer of reggaetón—a modern genre of Latin music originating in Puerto Rico, with sonic roots in Jamaican dancehall and American hip hop—Voltio officially retired from the music industry in 2014, having converted to Evangelicalism.

Orlando Javier Valle Vega, known professionally as Chencho Corleone or simply Chencho, is a Puerto Rican singer, songwriter and record producer. Considered one of the most important figures in the history of reggaeton, he is distinguished by his characteristic voice, which is considered one of the most distinctive and emblematic of the urban genre.

Benjamin Paul Ballance-Drew, better known by his stage name Plan B, is an English rapper, singer, songwriter, actor and filmmaker. He first emerged as a rapper, releasing his debut album, Who Needs Actions When You Got Words, in 2006. His second studio album, The Defamation of Strickland Banks (2010), was a soul and R&B album, and debuted at number one on the UK Albums Chart. He has also collaborated with other artists such as Chase & Status, most notably on the 2009 top ten single "End Credits".