iLe

From that point on, she began to collaborate as vocalist for the new musical project created by her famous brothers. Without any expectations of success, "La Aguacatona" caught the attention of White Lion Records, opening the door to what was to become a musical sensation. After recording a second song, "La Tribu", she was immediately nicknamed PG-13 by her cousin Ian Marcel Cardozo Joglar, since she was under-aged at the time she joined the group and PG-13 is normally used to classify movies that require parental guidance for children under 13.

During 2005, she was active in the late-night circuit of shows and presentations in various venues throughout the island, which would help give form and structure to what was to become Calle 13. At only 16 years of age, she found herself singing on stage in front of thousands at the Coliseo de Puerto Rico José Miguel Agrelot, as part of Calle 13's first concert. She chose to interpret "Puro Teatro", a song previously recorded by La Lupe, which is one of her favorite artists.

On May 2, 2009, Calle 13 performed once again at the Coliseo de Puerto Rico José Miguel Agrelot for the release of their third album Los de Atrás Vienen Conmigo. "In The Heights" playwright Lin-Manuel Miranda was invited to make an appearance after Residente had seen his acceptance speech for Best Original Score at the 62nd Tony Awards.[3][4][5] Backstage, Flor Joglar de Gracia, mother of iLe and Residente, revealed to Miranda their connection to Gilberto Concepción de Gracia, founder of the Puerto Rican Independence Party.[6][7] Miranda and Residente have since confirmed their family relation through social media.[8][9][10][11][12][13]

iLe continued traveling with Calle 13 during junior year of high school. At that time, she had the opportunity to visit other countries and share the stage with some of her most admired artists, such as Gustavo Santaolalla, Kevin Johansen and Susana Baca.

One of her most memorable performances took place when she was 18 and sang at the 8th Annual Latin Grammy Awards presentation held at the Mandalay Bay in Las Vegas, as part of Calle 13's interpretation of "Pa’l Norte" which opened with PG-13 belting out a powerful solo a cappella.[14]

In November 2011, Calle 13 opened the Gala at the 12th edition of the Latin Grammy Awards with the theme "Latinoamérica" performed with a symphony orchestra arrangement by Alex Berti and conducted by Musical Director Gustavo Dudamel. According to Latino Fox News, PG-13's high notes left everyone in silence.[15]

By the end of 2012 she participated in the traditional Banco Popular TV Christmas Special which has been produced and transmitted each year since 1993. On this occasion, for the special "Hecho con Sabor a Puerto Rico" Ileana had an impressive performance singing "La Pared"[16] which was described by the Diario of NY as "superb" 4 La Pared is one of the first successful songs written by Puerto Rican composer Roberto Angleró.

In 2010 she was invited by Kevin Johansen as a guest performer during his presentation at the Buenos Aires National Theatre where together they sang "Logo" a song included in Johansen's repertoire and recording; The Nada Liniers: Live in Buenos Aires.[17]

In 2012, she was chosen by famous boxing champion Miguel Cotto to sing the Puerto Rican National Anthem during the introduction ceremony prior to his fight against Floyd Mayweather Jr.. Her interpretation was widely acclaimed, including by the legendary Bob Dylan, who in 2015 mentioned her in his MusiCares Person of the Year speech: "I was in a boxing match a few years ago watching Floyd Mayweather fight a boxer from Puerto Rico and someone sang the Puerto Rican national anthem. And it was beautiful, it was heartfelt, it was moving".[18]

In 2014 she collaborated with Gustavo Cordera on the theme "Estoy Real" for the "Cordera Vivo" production, which was recorded at La Trastienda Club in Buenos Aires, Argentina. One year later, in 2015, she was invited by Jorge Drexler to sing on stage the song "Olas y Arena" by Puerto Rican composer Sylvia Rexach during Drexler's concert in Puerto Rico as part of the Uruguayan singer's tour.

In 2017, she guest sang on "Hijos del Canãveral", the closing track of her brother's debut solo album.[19]

In May 2016, iLevitable was released to the praise of critic and peers. According to NPR "the album established her immediately as a first-class interpreter of the classic sounds that flow through Latin America."[21] Jon Pareles of The New York Times described it as "a knowingly retro survey of Latin music's past, full of romance and a longing that can turn despondent. She sings richly orchestrated boleros, delicate ballads and percussive boogaloo and mambo, without a hint of either irony or naïveté."[22]

Some of Puerto Rico's most prominent musicians collaborated on the album: Piro Rodríguez, Charlie Sepulveda, Bayrex Jiménez, Eduardo Cabra, Fofé Abreu from Circo, Louis García and the late Cheo Feliciano in one of his last recordings ever.

The first single released was "Caníbal" and it was accompanied by a dramatic video directed by Argentinian Juan Manuel Costa. The video was described as an "animated Frida Kahlo painting"[23] and was positively reviewed.[24] Her second single and video, "Te Quiero Con Bugalú," was released on July 7.

Also in July 2016, Ile embarked on her first tour with her new band, performing the songs from iLevitable. On July 7, she performed at the Highline Ballroom as part of the Latin Alternative Music Conference Official Showcase.[25] July 8 she performed her first solo show outside of Puerto Rico—live at SOB's, also in New York.[26] Later that month she participated in the Nuevofest in Philadelphia and in the Millennium Park Summer Series in Chicago.[27] August 4 Ile performed at the Lincoln Center Out of Doors series, presented and recorded by NPR.[28]

In September 2016, The Recording Academy nominated Ile for her first Latin Grammy as Best New Artist.

In February 2017, iLevitable won a Grammy Award for Best Latin Rock, Urban or Alternative Album.

On May 20, 2019, iLe released her sophomore album, Almadura, a title that literally translates to "strong soul" and is a play on words of the Spanish word for "armor" ("armadura"). A natural continuation from her debut, this album contains many modern and electronic takes on Puerto Rican and other Caribbean musical styles and folklore, referencing traditional musical genres like bomba and boogaloo and featuring renowned artists like jazz and salsa pianist Eddie Palmieri.

Almadura not only reflects on Puerto Rico's cultural roots it, does the same reflections on its present and future, notably in the wake and aftermath of Hurricane Maria. Most notably, the album contains the critically acclaimed song "Odio," an activist track that imagines a free Puerto Rico and world in which "hate dies of hunger" ("el odio se muera de hambre").