Like the vulnerable confessions that define her songwriting, Alessia Cara’s performance at The Colosseum at Caesars Windsor on May 16 felt less like a concert and more like an evening spent with a trusted friend sharing secrets in her living room. The Toronto singer-songwriter transformed the 5,000-seat venue into an unexpectedly intimate space, delivering 23 songs that chronicled her journey from teenage uncertainty to hard-won self-acceptance.
Opening with “Dead Man” from her latest album Love & Hyperbole, Cara immediately established the evening’s tone—raw, honest and emotionally present. The five-time Juno Award winner appeared genuinely surprised by the enthusiastic response from the all-ages crowd, a demographic mix that perfectly reflected her cross-generational appeal. Her voice, stronger and more controlled than on record, carried easily through the venue without losing the conversational quality that makes her music so relatable.
The early portion of the set drew heavily from Love & Hyperbole, with “Left Alone,” “Run Run” and “Voice in My Head” showcasing the album’s themes of isolation and internal dialogue. Cara’s between-song banter revealed her natural comedic timing, frequently poking fun at her own anxiety while creating genuine moments of connection with audience members in the front rows. The stripped-back production allowed her vocals to shine, particularly during the vulnerable “Ready/Rooting for You.”
Mid-set highlights included “Subside” and “Drive,” where Cara’s band—a tight four-piece featuring guitar, bass, drums and keyboards—provided subtle but effective support. The singer’s stage presence has evolved considerably since her early career; she moved with confidence across the platform, using hand gestures and facial expressions to emphasize lyrical moments without appearing theatrical. Her performance of “Get to You” demonstrated remarkable vocal control, seamlessly transitioning between her lower register and soaring high notes.
The medley of “Better Days” and “Out of Love” provided one of the evening’s most emotionally resonant moments, with Cara’s delivery suggesting personal investment in every word. She followed with crowd-pleasers “Stay” and “Wild Things,” the latter prompting the first sustained sing-along of the night. The audience’s familiarity with these tracks created an energy boost that carried through “Nintendo Game,” where Cara’s playful side emerged fully.
“Somebody Else” and “Fire” maintained the momentum, with the singer encouraging audience participation without demanding it. Her approach felt organic rather than manufactured, allowing moments of quiet reflection between more energetic numbers. The production values remained consistently understated, focusing attention on Cara’s voice and the band’s musicianship rather than elaborate staging or visual effects.
The concert’s emotional peak arrived during “Slow Motion” and “Sweet Dream,” where Cara’s vulnerability felt most authentic. She spoke briefly about the challenges of young adulthood, acknowledging the audience members who had grown up alongside her music. These moments of connection—brief but genuine—reinforced the intimate atmosphere that defined the evening.
“Growing Pains” and “Apartment Song” continued the introspective thread, with Cara’s storytelling ability on full display. Her lyrics, examining themes of transition and uncertainty, resonated particularly strongly with the younger audience members. The singer’s ability to address serious topics without becoming preachy or overwrought demonstrated her artistic maturity and understanding of her audience.
The latter portion of the set included “You Let Me Down” and “Nighttime Thing,” where the band’s arrangement choices—subtle use of reverb, strategic silence—enhanced rather than competed with Cara’s vocals. Her performance of “Clearly” featured some of the evening’s most impressive vocal work, with sustained notes that showcased both technical skill and emotional depth.
The main set concluded with her breakthrough hits “Scars to Your Beautiful” and “Here,” transforming the venue into a massive chorus. These songs, which established Cara’s career and continue to define her public image, felt fresh rather than obligatory. Her delivery suggested continued personal connection to the material, avoiding the rote quality that can affect artists performing their biggest hits repeatedly.
Toronto R&B artist Jon Vinyl opened the evening with a confident set that made full use of The Colosseum’s expansive stage. The 24-year-old performer delivered smooth vocals over contemporary R&B arrangements that drew clear influences from Miguel and Frank Ocean. His stage presence was commanding without being aggressive, and his between-song commentary revealed both humor and genuine appreciation for the opportunity to perform in such a prestigious venue. Songs like “Addicted” demonstrated his ability to craft modern slow jams with old-school sensibilities.
All photos by Dan Savoie
Alessia Cara:
Jon Vinyl:
