Published 10 years after his previous studio album, Legendaddy is Daddy Yankee's last record, as he announced that he would retire from music after the end of his farewell concert tour, La Última Vuelta, in 2023.

It features collaborations with Bad Bunny, Becky G, El Alfa, Lil Jon, Michael Buffer, Myke Towers, Natti Natasha, Nile Rodgers, Rauw Alejandro, Pitbull, and Sech.

[8] In 2019, Vice contributor Gary Suarez opined that it was "either completely dead in the water or overdue for a radical revision from what he originally intended," while Ulises Fuente of La Razón anticipated that it might not be released because of the success of his standalone singles.

[10] On September 10, 2020, Daddy Yankee closed a global distribution deal with Universal Music Group with plans of releasing a new album and producing a documentary about the history of reggaeton.

[13] On September 15, 2021, Billboard's Leila Cobo stated that the then-unnamed album would release in the fall, while Daddy Yankee hinted at a retirement and said that he saw himself growing as an executive producer of movies and documentaries.

[16][17] On March 20, 2022, he posted a video on his social media in which he announced that he would retire from music after the conclusion of his upcoming farewell concert tour, La Última Vuelta, as well as the release date for his final album, Legendaddy.

[24][26] He decided to feature a track list consisting entirely of new songs, without including previously released singles from past years, stating that "it would make an impression because it's something that isn't done anymore.

[32][33][34] Primarily a reggaeton record, both old-school and contemporary, Legendaddy also incorporates trap and elements of salsa, bachata, cumbia, dembow and electronic dance music.

[34][37][42] "Pasatiempo" features Puerto Rican rapper Myke Towers and blends reggaeton with a repeating sample of the melody of Swedish producer StoneBridge's remix version of the house single "Show Me Love" (1992) by American singer Robin S., with lyrics about casual sex and a woman who wants to have fun at a nightclub and "take out the beast" she has inside.

[47][48] "X Última Vez" features Puerto Rican rapper Bad Bunny and is a "sad and nostalgic" song that blends "old-school reggaeton beats with edgy urban sounds,"[14] with lyrics about "wanting to rekindle old flames" one last time[36] and "finally saying goodbye to a relationship.

[34][41][54] The next song, "Agua", is a "1980s-inspired dance" track that features vocals by Puerto Rican singer Rauw Alejandro and electric guitar funk riffs by American guitarist and producer Nile Rodgers.

[36][37] "El Rey de lo Imperfecto" is a romantic "urban-infused cumbia song" about an imperfect man "promising to unconditionally love a person through her own insecurities and drama.

[56][57] American production duo Play-N-Skillz, producers of Daddy Yankee's "Con Calma" (2019), worked on six tracks, including the singles "Agua", "Hot", "Bombón" and "Pasatiempo".

[39][61][62] Dominican producer and longtime collaborator Luny—one half of production duo Luny Tunes, who worked on Daddy Yankee's breakthrough album Barrio Fino (2004) and its single "Gasolina"―produced two tracks, including "Rumbatón".

[73][74] It depicts the head of a mature, aged, wounded and bloodstained goat with golden horns, which has been interpreted as Daddy Yankee's experience and his "royalty, wealth, or high social status," as well as a "resistance symbol".

[87] It is Daddy Yankee's highest-charting album in the country and his second top 10 after El Cartel: The Big Boss (2007),[87][88][89] although it left the chart after six weeks, becoming his fifth longest-running entry on the Billboard 200.

[106][107][108] It was accompanied by a music video directed by Dominican filmmaker Marlon Peña, which depicts a newlywed couple that end up joining a street party in Cabo Rojo and features cameos by Luny, DJ Joe and Trébol Clan member Periquito.

[119][120][121] It was the 89th song with most radio spins of 2022 in Latin America, with 95,520,[122] and was the album's most-played track of the year in Bolivia,[123] Chile,[124] Costa Rica,[125] Ecuador,[126] El Salvador,[127] Panama,[128] Peru,[129] Spain,[130] Uruguay,[131] and Venezuela.

[120] The eighth single, "Pasatiempo", was released on July 28, 2022, through a music video directed by Miami-based director José Sagaró,[174] which incorporates "vintage elements" and a "black and white minimalistic setting".

[120][139] "La Hora y El Día", the album's first bonus track, was released on February 16, 2023, alongside a music video directed by Venezuelan director Nuno Gomes.

[127] Visualizer videos for the tracks "Enchuletiao'" and "Campeón", both filmed during his farewell concert tour and directed by Marlon Peña, were released on November 23, 2022, and December 22, 2022, respectively.

[210][211] Legendaddy received mostly positive reviews from music critics, who referred to it as a good send-off for Daddy Yankee's retirement[35][214] and commended his performance and the album's blend of nostalgic and contemporary reggaeton tracks,[34][36] as well as its incorporation of other genres.

[14][38] Describing Legendaddy as Daddy Yankee's best album since Barrio Fino, Gary Suárez of Rolling Stone commended its "forward-looking approach" through contemporary tracks and the choice of a "younger crop of identifiable" vocal collaborators.

[35] However, he found the record to have "its flaws, largely reflecting [his] history of making iffy decisions that lead to uneven albums," although he also stated that it is a "blaze of glory" for his retirement, "a Latin icon ending things on his own terms.

"[35] His delivery and flexibility were praised as sounding "electric [and] deliciously abrasive", as well as "fast, energetic [and] intoxicating,"[34][214][215] with Isabela Raygoza of the Grammy Awards website commending the album for "[encapsulating] his dynamic and linguistic prowess," with "plenty of moments [...] where [his] creative brilliance shines through.

[214] While Rolling Stone's Gary Suárez commended Legendaddy for its "tacit rejection of nostalgia,"[35] Isabelia Herrera of The New York Times stated that "the most dynamic moments come when [Daddy Yankee] reaches for the magic of the past,"[34] while Spin's Lucas Villa praised it as an "impressive amalgamation of reggaetón's legacy".

[36] Herrera also praised "Uno Quitao' y Otro Puesto" as a "corrosively effective blast of late-career posturing," "Enchuletiao'" as a "reminder of his technical skills" and "Remix" and "Bloke" as "classic reggaeton romps".

[34][35] Reviewing the album for The New York Times, Isabelia Herrera found a "good portion of the songs" to follow "prosaic, predictable pop formats," describing "Para Siempre" as a "bland, mid-tempo popeton ballad" and "La Ola" and "Zona del Perreo" as sounding like "they were engineered for Spotify's 'Viva Latino' playlist.

[14][38][45] The album's collaborations were generally approved, with some of them—including "Pasatiempo" and "X Última Vez"—being selected by critics among its best songs,[14][35][41] while Cruz Bonlarron Martínez of American media outlet Latino Rebels noticed the absence of Don Omar, Puerto Rican duo Wisin & Yandel and American singer Nicky Jam, but understood that its guest features "give [it] a more contemporary sound, placing it closer to the new wave reggaeton".

[218] On the contrary, Luis Maínez of Spanish magazine Mondo Sonoro criticized the featured artists for "falling short of the opportunity they were given" and wrote that the record lacks the "epic moments" like the ones that helped to improve Daddy Yankee's career.