Paid In Memories Tour: Jessie Reyez and RAAHiiM - Winnipeg, MB

Jessie Reyez’s long-awaited first appearance in Winnipeg finally came on November 28, 2025. The Burton Cummings Theatre became a sanctuary, vibrating with the raw honesty, smoky vocals, and fearless storytelling that have defined Reyez’s entire career. For fans who had waited years to see her live, this night felt like both a celebration and an overdue homecoming.

RAAHiiM. All photos by Samuel Stevens.

Opening the night was rising R&B artist RAAHiiM, whose velvety tone and atmospheric instrumentals warmed the room instantly. His set was a perfect pairing for Jessie’s energy—smooth, introspective, and intimate. RAAHiiM navigated between moody slow burns and soulful grooves, and a couple of covers to boot, earning cheers that echoed surprisingly loudly for an opener. By the time his set ended, the crowd was fully tuned into the emotional frequency Jessie would soon amplify.

When the lights dimmed, and Jessie Reyez stepped into the soft glow of the stage, the audience erupted. She opened with the defiant “I NEVER SAID I WAS SANE,” immediately setting a tone of vulnerability mixed with fire. “BEGGIN 4 LUV” and “GOLIATH” followed, showcasing her ability to make even the biggest theatre feel personal—as if she were singing directly to each person there.

One of the most unforgettable highlights came during “NYB.” As Jessie moved across the stage, she asked for someone to come on stage to dance with her, then her dad walked onto the stage to join her, dancing with uninhibited joy while the crowd roared. Jessie’s smile said everything—it was a tender moment that made the show feel even more special for her first-ever time in Winnipeg.

Jessie’s setlist was a masterclass in emotional pacing. From the spiritual undercurrent of “PALO SANTO” to the psychedelic tenderness of “PSILOCYBIN & DAISIES,” Jessie wove vulnerability into every note.

She pivoted effortlessly into fan favourite songs like “Shutter Island” and “Gatekeeper,” songs that still hit with the same righteous fury and emotional weight they carried upon their initial release. The pair of tracks, “Coffin” and “6LESSINGS,” continued the intensity before the night took a soulful turn with “Forever,” “Imported,” and the iconic heartbreak anthem “FIGURES,” which had the entire theatre singing louder than the venue's sound system.

Moments of hype broke through as well—“Great One” and “Apple Juice” radiated hope and warmth, while “Mutual Friend” and “L.O.Y.L.” reminded everyone how potent Jessie’s pen is when she’s pulling from the messiest corners of love.

Jessie Reyez. All photos by Samuel Stevens.

The tail end of the set hit just as hard as the opening: “Sola,” “RIDIN,” “JEANS,” and “CUDN’T B ME” showcased Jessie’s versatility, swinging from sultry grooves to passionate crescendos. What stood out most, though, was her connection to the room—she spoke candidly between songs, laughed with fans, and made the crowd feel like they were part of something she’d remember and something she wanted her fans to forever remember, too.

Earlier in the night, on the stage's screen, Jessie had asked fans to vote via a QR code for the encore. The options were “Free,” “Still C U,” or “Tonight We’ll Never Have.” The results were revealed only when she returned back to the stage and the first note of “Free” hit, declaring it the winner of the three. The encore felt almost ceremonial. Under soft lights, Jessie delivered “Free” with aching clarity, turning the theatre into a collective exhale. It was the kind of moment that stays with a crowd long after the final note fades.

Jessie Reyez’s debut Winnipeg performance wasn’t merely memorable—it was the kind of show that instantly enters local concert lore. With a powerhouse setlist, a theatre full of devoted fans, and a performance that swung effortlessly between fierce and fragile, Jessie made it clear that the Paid In Memories Tour is one of her strongest chapters yet. If this is what she brings on her first visit, Winnipeg will be more than ready for her return.