Ileana Cabra Joglar, the Grammy-winning singer known simply as iLe, brings her full band from Puerto Rico to Little Haiti's ZeyZey this Friday night, October 30, at 9 p.m., mixing two decades of solo material with songs from her recent bolero tribute album. The show will pull from throughout her 20 years as a solo artist, blending original compositions with the stripped-down torch songs that have defined her latest chapter.
From Calle 13 Backup Vocals to a Bolero Obsession
Long before she was iLe, Ileana Cabra Joglar sang backup vocals as an adolescent for Calle 13, the celebrated Puerto Rican band started by her brothers, Residente and Visitante — René Pérez Joglar and Eduardo Cabra Martínez. She performed with the group under the name PG-13 for a decade, during which Calle 13 built its reputation on rap, urban music, and sharp criticism of Puerto Rico's economic and social inequalities. iLe began her solo career in 2016, and her debut album, iLevitable, won a Grammy for best alternative rock album, according to El Tiempo.
That same grounding in resistance music carried into Puerto Rico's streets in 2019, when iLe joined Bad Bunny and Residente to write Afilando los cuchillos, a song that became an anthem for the movement to remove then-Gov. Ricardo Rosselló. Leaked messages had revealed Rosselló's contempt for ordinary Puerto Ricans, and thousands of people protested in response to the leak, public corruption allegations, and the government's faltering response to Hurricane María. iLe joined those protests alongside Ricky Martin, Bad Bunny, and Residente, and Rosselló resigned after 12 days of demonstrations, becoming the first governor in Puerto Rico's history to do so.
A Tribute Album Rooted in Family
iLe's connection to bolero took hold during her own adolescence, when her father introduced her to Cuban female singers of the genre, deepening a pull she felt from the very first listen, as reported by PRPOP. That fascination eventually produced Como las canto yo, released in October 2025 as a 21st-century homage to the Cuban torch songs popularized by divas of the 1950s and 1960s. Per the Los Angeles Times, the album is a tribute to the same musical tradition that first captivated her, and iLe has described her pull toward bolero as a mix of orchestral grandeur and intimate, guitar-centered storytelling — “Me gustaba mucho ese drama, esa pasión que tenía, y ese lado bien grandioso de orquesta, pero al mismo tiempo, la parte más íntima, de guitarra,” she told La Times.
Rather than lean on lush orchestration, the record forgoes that trapping in favor of a grittier aesthetic, Rolling Stone reports, calling the project a tribute to iLe's obsession with the bolero mystique. The album includes just one original, previously unreleased composition: No te detengas, written by iLe's grandmother, Flor Amelia de Gracia Barreiro, per the same outlet's reporting. Among the first boleros iLe recorded was La pared, written by Roberto Angleró, and she kept its lyrics unchanged when she sang it — insisting, as she has said, that everyone should be able to sing songs to whomever they choose, regardless of gender.
Boleros With a Feminist Edge
Boleros often dealt with love and heartbreak, but iLe has pointed out that the genre's romantic surface can mask something darker. “Hay un montón de boleros que parecen románticos, pero, en realidad, son violentos y machistas,” she told El Tiempo, suggesting that performing them from a woman's perspective can expose that violence and sexism more forcefully. The album's inclusion of her grandmother's song, alongside a deliberate reworking of gendered lyrics elsewhere in the repertoire, reflects that same impulse. The Fundación Nacional para la Cultura Popular recognized Como las canto yo among its 20 outstanding recorded productions of 2025, according to PRPOP.
iLe's solo catalog extends well beyond bolero. At the 18th concert of Bad Bunny's San Juan residency last year, she performed her own interpretation of his song Lo que le pasó a Hawaii. She has said that music and art offer new perspectives and raise questions about people's current experiences — a philosophy that extends to how she thinks about live performance itself, noting that live settings offer companionship and a chance for audiences to support one another.
What to Expect at ZeyZey
For Friday's show, iLe hopes to create a communal, collective space for the audience, according to WLRN. She will perform boleros and original material with her five-piece band, bringing the full lineup from Puerto Rico: guitarists Adalberto Rosario and David Díaz, bassist Jonathan González, drummer Ismael Cancel, and percussionist Yreri Irady. General admission runs $34.90, with VIP admission at $57.85; attendees under 18 must be accompanied by a parent or guardian. VIP table reservations can be made by texting or emailing Brooks Smith, and general information is available by phone at (305) 456-2671.
The venue itself has become one of Little River's more unlikely cultural anchors. ZeyZey opened in summer 2023 as a pop-up music venue and culinary hub, according to Time Out Miami, and its programming initially leaned on a Latin-focused mix of Afro-Cuban funk, Brazilian disco, salsa, boogaloo, cumbia and Afrobeat sounds. The space maxes out at 1,000 people, and its resident kitchen is run by Tacos María, described on the venue's own site as the rebellious little sister of Los Félix.
ZeyZey's bookings have grown steadily more ambitious since a sold-out Poolside show in March 2024 marked the venue's first sellout, followed by a sold-out performance from Santigold, per Time Out's reporting. The operators have said the plan is to stay in the neighborhood while eventually expanding to a venue that can accommodate more attendees and bigger artists — a trajectory that now includes a Grammy-winning bolero interpreter steeped in Puerto Rico's protest history taking the stage in Little Haiti.
