During his time with the group, he produced, wrote and was the lead singer in the songs "9:15", "Déjà Vu", "Voy Malacostumbrado", and Princesita as well as being the background vocalist in most tracks.

He has been featured in other songs with other artist, including Bad Bunny, Anthony Santos & Pavel Núñez.

He is the cousin of bachata star Romeo Santos, with whom he co-founded Los Tinellers in 1994 in what would later become the group known today as Aventura.

In 1995 they met a man by the name of Elvin Polanco who would eventually manage and help them record their first album titled Trampa de Amor.

Aventura released their debut album in 1999 titled Generation Next with the hopes of bringing bachata into the mainstream from its traditional base and fuse it with hip hop and R&B.

In 2002, the song "Obsesión" achieved huge success in many countries, topping many international charts in France, Germany and Italy.

After breaking multiple records and selling out arenas and stadiums, the group split in 2011 to work on separate projects.

In 2011, after his success with Aventura, he would start a solo career while the rest of the members would also work on separate projects.

It was released under exclusive licensing to VeneMusic & Universal Music Group, executive produced by HustleHard Ent.

The album featured collaborations with El Adictivo Sonido L.A.X., Bobby Pulido, Maffio, and Natti Natasha.

On April 14, 2014, TR3S launched an exclusive campaign featuring Henry Santos' third video La Vida, in collaboration with Latin Grammy award winning producer Maffio.

[4] On December 1, 2015, it was announce that Aventura would reunite to have a series of concerts for the whole month of February 2016 at the United Palace Theater in New York City.

The album featured collaborations with Jhoni The Voice, Leoni Torres, Maffio, and Gente De Zona.

On May 3, 2019 he released "Don Juan & Cupido" with Anthony "El Mayimbe" Santos as the first single for his fifth studio album.

2019, he reunited again with the group at his cousin Romeo's sold out concert at MetLife Stadium to close the show.

On January 24, 2020, he released the sequel to his first karaoke album Reto: Canta Con Henry Santos Vol.2 (Los Clásicos).

It also featured Ronny Mercedes who was a participant of the American Spanish-language singing competition television series, La Voz.

But instead of doing the shows in the venues that were originally planned before their cancelation, they decided to play at stadiums and big arenas in certain cities.

[10] Before the tour started, the group released the single Volví on August 3, 2021, featuring Bad Bunny.

Their last 2 shows together were on December 18 and 19, 2021, Félix Sánchez Olympic Stadium in Santo Domingo, Dominican Republic.

[13][14] After the Inmortal Tour, Henry return to continue with his solo career and began working on his sixth studio album.

On October 6, 2023, he released the bachata single "No Soy Nada Sin Ti" with Frank Reyes.

The music videos for both "La Excepción" and "No Soy Nada Sin Ti" are part of a series involving romance and boxing.

Henry Santos have make cameos in two successful Dominican movies, Sanky Panky and La Soga.

[23] In September 2012, it was announced that Henry Santos would be the first dancer from the Dominican Republic involved in the third season of Mira Quien Baila, Univision's Spanish version of Dancing with the Stars.

Santos was crowned by the fans "El Rey de la Pista" (King of the Dance Floor) with over 41% of the votes against Alicia Machado and Fernando Arau.

[26] Competing in Mira Quien Baila, Henry Santos represented the National Latino Children's institute as support for the organization.

[25] On May 6, 2014, Santos partnered up with NYC Presbyterian Hospital & Columbia University in the fight against child obesity in the United States with their community program "Vive Tu Vida" by CHALK, offering a healthy alternatives menu in restaurants all over NYC and educating Latinos on recommended portion sizes for foods, the benefits of exercising and a healthier lifestyle.

[27] Subsequently, Santos represented his foundation in the popular Telemundo cooking competition Top Chef Estrellas with the purpose of spreading the message.

[28] On May 14, 2014, Santos was named the "Padrino" (Godfather) of the Latino Commission on AIDS in the United States, helping spread the word among Latin people on the fight against this illness.