His 2016 mixtape Real Hasta la Muerte was well-received, but his success was put on hold the same year by a 30-month prison sentence for illegal firearm possession in Puerto Rico.

In November 2020, Anuel AA made a statement on Instagram and released a new song suggesting his imminent retirement from the music industry, citing family and relationship issues.

While he does not identify as a fan of the salsa genre, Anuel AA recalls that seeing his father interact with these artists inspired an interest in the recording industry.

[3] However, his father lost his job when Anuel AA was fifteen years old; this led him to become what Rolling Stone magazine described as a "son of the streets".

[5] In April 2016, Anuel AA was arrested in Guaynabo, Puerto Rico, and sentenced to 30 months in federal prison for illegal possession of three firearms.

[11] In the six months following the release of Real Hasta la Muerte, Anuel AA contributed vocals to eleven Billboard Hot Latin Songs-charting singles, including "Ella Quiere Beber" with American singer Romeo Santos.

[13] In January 2019, the rapper released the single "Secreto" with Colombian singer Karol G, confirming the romantic relationship between the two artists in the song's accompanying music video.

[6] Also in April 2020, Anuel AA released the single and video for "Follow" with Karol G, recording it entirely while in quarantine in Miami due to the COVID-19 pandemic.

"[2] The 22-track double album features collaborations from Bad Bunny, Enrique Iglesias, Travis Barker, Tego Calderón, Karol G, Lil Wayne, Farruko, Yandel and Ñengo Flow.

[26] On November 19, he released a new track, "Me Contagié 2", in which he talks about depression, indicates unhappiness with his relationships and expresses anguish at the fact that his career often takes him away from his young son, who has asked him to retire.

[citation needed] The company's activation with UFC included Anuel AA's visuals, logo, and artistic concept for his third album, Las Leyendas Nunca Mueren.

On 20 May 2022, Anuel AA partnered with Chris Jedi, Chencho Corleone and Ñengo Flow in global hit "La Llevo al Cielo".

Anuel AA announced the EP Me Fui de Gira with 6 or 7 tracks but later he cancelled it and unified it with the upcoming album Las Leyendas Nunca Mueren 2.

[citation needed] In February 2024, Anuel AA alongside Ozuna featured on the single "Bad Boy" by Chris Jedi, Gaby Music and Dei V. Later he appeared on the deluxe edition of Jennifer Lopez's album This Is Me... Now in the remix of "Rebound".

[37] In March 2024, he took part of the remix of Pressure 9X19's "VVS Switch" alongside Puerto Rican rappers YOVNGCHIMI, Hades66, Luar La L and CDobleta.

[1] Paul Simpson of AllMusic described his lyrics as "too risqué to be played on the radio" and highlighted that his success has instead stemmed from streaming services and the artist's highly active social media presence.

[1] Gary Suarez of Vice viewed his 2018 album Real Hasta la Muerte as a collection of both "gleaming trap bangers" and "reggaeton crowd pleasers".

[5] Despite his "bad guy image", Suarez wrote that the relationship-themed songs "Culpables" and "Secreto" represent "a softening of his hardened trapero persona".

Examples include "China" which samples both "It Wasn't Me" by Shaggy and "Ella Me Levantó" by Daddy Yankee, and "Delincuente" which interpolates "Bandoleros" by Don Omar and Tego Calderón.

[42] He is influenced by, and has collaborated with, American hip hop artists Meek Mill and Gucci Mane, both of whom, like Anuel AA, gained notoriety for serving time in prison.

"[18] In an interview with Vice, he expressed admiration for the music of bachata artist Zacarías Ferreíra, Dominican rapper el Alfa, and English singer-songwriter Ed Sheeran.

[44] Due to the public backlash, Anuel AA's concert at the Coliseo de Puerto Rico venue, scheduled for October 12 of that year, was canceled by his production staff and main producer Paco López.

To homosexuals, to people with AIDS, to La Taína [the model] and to those who lost everything after Hurricane Maria ... My fans deserve from me to be a better person, and I apologize to everyone in Puerto Rico.

The possible reason for the release of track is due to Anuel ending his business relationship with his longtime manager Frabián Eli, who is Arcángel's brother-in-law.

Also responding to Arcángel again through an Instagram post, Anuel claims that nobody noticed that he released his album, Sentimiento, Elegancia y Más Maldad, adding that "[he's] waiting for Bad Bunny to collaborate with him to revive his career.

[52] Anuel AA met Colombian singer Karol G in August 2018 on the set of the music video for their song "Culpables", a month after his release from prison.

[12] On April 25, 2019, Karol G arrived at the Billboard Latin Music Awards wearing a "massive" diamond ring, confirming the couple's engagement.

Anuel AA accepted the invitation of the former President of the United States Donald Trump to participate and support his 2024 presidential campaign in Johnstown, Pennsylvania.

Anuel AA was arrested and held in the Metropolitan Detention Center, Guaynabo on April 3, 2016, with three companions when police found three pistols including one stolen, nine magazines, and 152 bullets.

The rapper's NFT collection will be made up of physical assets along with exclusive real life experiences such as limited edition merchandise, access to album release parties, studio visits and listening sessions.