There's something profoundly counterintuitive about voluntarily paying money to have your heart ripped open in public. Yet here I was, at Massey Hall, clutching a complimentary tissue packet like a lifeline, fully aware that Sara Bareilles was about to make me feel things I'd spent weeks successfully avoiding. And honestly? It was exactly what I didn't know I needed.
What makes this concert experience particularly fascinating is how it challenges everything we think we know about pop concerts. We go expecting spectacle, expecting to be entertained, maybe expecting to scream along to our favorite anthems. We don't typically expect to be led through an emotional excavation in a 2,500-seat venue that smells faintly of old wood and collective anticipation. But that's precisely what Bareilles delivered on Tuesday night—a grief workshop disguised as a concert, or perhaps a concert disguised as a grief workshop. The distinction, I found myself thinking throughout the evening, might not actually matter.
The genius of this tour lies in its audacity. Bareilles, whose previous work includes the irresistibly peppy "Love Song" and the Broadway hit "Waitress," has built a career on accessible, piano-driven pop that makes you tap your feet. Now she's asking audiences to sit with loss—not metaphorically, but quite literally. The branded tissue packets stationed around the venue weren't a gimmick; they were an acknowledgment that this evening would demand something from us. In my opinion, that kind of honesty from an artist is rare and genuinely brave.
From my perspective, what struck me most was how Bareilles weaponized her own likability. Here's an artist who could have released a somber, acoustic-heavy album about grief and toured it as a somber, acoustic-heavy experience. Instead, she threaded humor throughout "Good Grief," that new record exploring everything from death to political disillusionment to the particular agony of infertility struggles. She can write a bluesy, jazz-tinged song about having a nervous breakdown and somehow make it feel like an intimate conversation with a friend who happens to be musically gifted. Who else could pull that off? I'm genuinely hard-pressed to think of another artist walking this tightrope between devastation and levity with such apparent ease.
What many people don't realize is that the concert's emotional architecture was carefully constructed. The evening didn't simply alternate between sad songs and happy ones; it created a rhythm that mirrored how we actually experience grief in real life. There were moments of genuine lightness—a surprisingly joyous Whitney Houston cover that turned Massey Hall into a dance party—interspersed with devastating pauses. The fan voicemail recordings, submitted in advance and played over the speakers, felt like communal confession. We heard from an 80-year-old widower, from someone in the trenches of IVF treatment, from a person mourning a friend lost too young to cancer. Each story was carefully curated to complement the album's themes, yet these strangers' voices created something unexpected: a sense that we were all in this together, that grief is somehow both deeply personal and universally shared.
One thing that immediately stands out is how Bareilles handled the political dimension of her grief. She mentioned loving her country in terms that clearly referenced the current American political climate without ever naming names. This "grief of country," as she called it, resonated with a particular sharpness. In my experience, this kind of grief—mourning for a nation that feels unrecognizable—is rarely addressed in popular music, let alone in a pop concert setting. It felt like a small act of defiance, acknowledging that yes, we are all carrying collective wounds alongside our personal ones.
If you take a step back and think about it, the concert raised deeper questions about why we seek out sad experiences in controlled environments. There's been plenty written about the psychology of crying at concerts, but I think we undersell what's actually happening. When Bareilles closed her eyes to listen to those voicemails—probably for the hundredth time on this tour—she wasn't just performing empathy. She was modeling it. She was showing us that grief doesn't have to be solitary, that it's okay to lean into the pain rather than immediately reaching for distraction.
This is where I think Bareilles has accidentally become something unexpected: a grief counselor for the social media generation. Not in a clinical sense, obviously, but in the sense that she's created a space where vulnerability is the point. The a cappella singalong of "You Matter to Me" when an audience member requested it and she declined to play the full version—that moment captured the evening's essence. She wasn't giving us what we wanted; she was giving us what we needed. And in a time when we're all drowning in performative positivity, that feels almost radical.
A detail that I find especially interesting is the concert's length—over two hours, which is substantial for any performer but particularly for someone asking audiences to maintain emotional openness for that duration. Yet the evening never felt exhausting. It felt, strangely, like relief. There's something cathartic about crying in a room full of strangers who are also crying, about releasing the tension you've been holding privately for weeks or months or years. The weightlessness I noticed in even the saddest songs—particularly "Still Crying," where Bareilles hit high notes seemingly without effort—suggested that perhaps grief, when shared, becomes more bearable. Not lighter, necessarily, but more bearable.
What this really suggests is that we've entered a new phase in how artists relate to their audiences. Bareilles isn't performing emotion; she's curating an emotional experience and then stepping aside to let it unfold. She's created what amounts to communal therapy disguised as entertainment, and the fact that it's also genuinely entertaining is almost beside the point. Almost.
The concert closed, as these things do, with a sense of unfinished completion. Grief doesn't end, after all, and neither did this evening really—it just reached a natural pause. As I walked out into the Toronto night, tissue packet now empty in my pocket, I found myself thinking about all the ways we typically avoid sitting with difficult feelings. We scroll through our phones, we watch mindless television, we do anything to bypass the harder emotions. But Bareilles asked us to do the opposite, and we showed up for it. Thousands of us, paying for the privilege of feeling terrible together.
In my opinion, that's not masochism. That's humanity finding new ways to connect in a world that often feels increasingly disconnected. And if getting there requires a bowler hat, some jazz-inflected heartbreak, and more tissue packets than any concert should reasonably need—well, I'm not complaining. Sometimes the strangest paths lead to exactly where we need to be.
