From the moment the doors opened, excitement buzzed in the air. The theatre filled quickly, with a sold-out crowd dressed to impress in their best throwback outfits—think butterfly clips, jean skirts, Juicy Couture tracksuits, and enough bedazzling to light up the stage. Early 2000s bangers pulsed through the sound system, complete with heavy bass and catchy hooks, as fans danced in their seats and belted the lyrics. Then, with a burst of energy, Jessi made her grand entrance.

Dressed in a dramatic red puffer jacket and flame-accented red sunglasses—an homage to peak 2000s fashion—she strutted onto the stage to thunderous applause. In a theatrical flourish, she tore off the jacket and flung it into the crowd, sending the energy in the room skyrocketing. Without missing a beat, she kicked off her set by inviting four fabulously dressed audience members on stage for a full-blown dance-off. What followed was a riotous display: two Pitbull lookalikes, an Avril Lavigne doppelgänger, and one woman embodying the full chaotic spirit of 2005 “dropped it like it was hot” to roaring laughter and cheers.

Jessi’s comedic timing was flawless. Her set was a rapid-fire series of personal stories, outrageous observations, and lovingly savage millennial truths. One highlight came when she recounted enrolling her son in piano lessons with a woman known only as “Shelly the Piano Whisperer.” With perfect dramatic irony, she played a recording of his performance—lovingly described as a “horrible monstrosity”—to gasps and guffaws from the crowd.

The show took an even funnier turn as Jessi skewered the tech illiteracy of middle-aged men, calling up an unsuspecting male audience member to display his Instagram feed on the theatre’s massive screen. As she swiped through truck photo after truck photo, including a particularly memorable image of a white pickup stuck in a Dollarama snowbank, the crowd erupted in uncontrollable laughter.