At Massey Hall, Sara Bareilles walked audiences through her grief – and shepherded them through their own

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We should have known what we were in for. At Sara Bareilles’s intimate concert at Toronto’s Massey Hall on Tuesday night, free packets of Bareilles-branded tissues were available for the taking at stations around the venue. You’re going to cry, the stacked Kleenex seemed to warn. Best take one of us before you do.

On the whole, Bareilles is not known for being sad. Her piano-heavy back catalogue deals jointly in affable doo-wop pop and musical theatre; her fashion choices, Tuesday night’s Charlie Chaplin-adjacent bowler hat included, tend toward twee.

But in August, Bareilles released Good Grief, an album that explores the specific pain of loss in all its shades. The record’s themes are as tough as you’d expect – feelings about death and dying intertwine with longing for a pre-Donald Trump United States – but the bluesy humour for which Bareilles became famous in the late 2000s sparkles across the album. (Could any other artist pull off a smiley, jazz-tinged croon about a nervous breakdown? I’d wager not.)

Sara Bareilles grieves both a friend and the U.S. on her new album

On Tuesday, her first concert in Toronto since 2013, Bareilles sang through most of Good Grief and a few longstanding hits, welcoming us to join her on the road to inner peace. Loss, she explained, is best managed in community with others, an idea investigated at length on her latest album: “Tell me your story, I’ll tell you mine,” she implores on Home, the record’s opening track and the first song on its accompanying tour’s setlist.

Enter tissues.

It’s not that Tuesday’s tour stop was uniformly tearful. In fact, for much of its two-hour-plus runtime, the gig felt surprisingly airy, a dual showcase of Bareilles’s satiny voice and sharp wit. A jaunty Whitney Houston cover – you can guess of what song – saw Massey Hall transform into a 2,500-person dance party, creating a brightly-lit partition between Bareilles’s new record and the assortment of past chart-toppers at the end of her set. Playful jokes from the audience, too, were answered rather than ignored.

Even Good Grief’s saddest songs, lush with complex instrumentation, betrayed a striking sort of weightlessness: Still Crying saw Bareilles repeatedly hit a high B-flat, seemingly without even blinking. (“That song is sponsored by high notes,” she quipped between long sips of water while the audience roared.)

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But Bareilles, 46, has spent the last decade working through real pain. She’s lost friends; she’s struggled with infertility; she’s seen her country devolve into a strange facsimile of its past ideals. “I want to be able to love my country,” she said between songs, vaguely condemning Trump without ever saying his name. Of the types of grief she claims as hers, “grief of country” is among the most cutting, she said.

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Where the night got weepy was in pretaped recordings submitted by fans and played over the venue’s speakers between songs: “Remember answering machines?” cracked Bareilles as she introduced the project. In each recording, an anonymous stranger – a widower in his 80s, a parent-to-be at the finish line of a gruelling IVF journey – unleashed their experiences of loss.

Some of the voicemails suggested acceptance; others conveyed feelings of rage, denial, depression. Carefully curated to complement the themes of Bareilles’s new album – Ladies in a Line’s fed-up account of trying to conceive, Just a Kid’s requiem for a friend who died far too young from cancer – the voice memos felt like vital supplementary material for the record, never cheesy or extractive in their emotional wallop.

When Bareilles closed her eyes to listen, undoubtedly for the dozenth or so time, there was no doubt she was hearing each story with fresh ears – that some new detail had connected with her as free tissue packets crinkled in the otherwise silent audience.

Even a more cynical critic would struggle to find evidence that Bareilles is not as warm offstage as she is when she sings. Her first words on Tuesday night – “Hello, Toronto!” excluded – were effusive thanks for the crew who managed to fit a set designed for larger spaces on Massey’s cozy stage. When an audience member loudly requested a song Bareilles had no intention of playing – You Matter to Me, a duet from her musical Waitress – she sweetly declined before leading the venue in a short, a cappella singalong of the ballad’s chorus.

In a time of profound suffering – on personal, political and global levels – there’s something to be said in favour of a big cry and kindness for kindness’ sake. Deeply sentimental and unexpectedly funny, Bareilles’s Toronto tour stop offered fans a community to trade stories of heartache, both with each other and with Bareilles herself. Never before has grief felt so good.