Oh Jimmys

And you thought the Tonys were dramatic.

This past Monday, 116 high school students walked onto the stage of the Minskoff Theatre for the Jimmy Awards. Two of them left with twenty-five thousand dollars and a head start on the rest of their lives.

If you love theater, the Jimmys do something strange to you.

Last year I wrote about the Jimmys from the outside in—how a small digital team turned a niche ceremony into a forty-million-view phenomenon. This year I want to talk about what the night does to the rest of us, the ones watching from the couch with a lump in our throats we can't quite explain.

Geronimo.

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The Stage

In case you've never seen them: the Jimmy Awards—officially the National High School Musical Theatre Awards—are something like a national championship for teenage musical-theater performers. All year, regional programs around the country crown their own winners. Those winners get flown to New York, where for 10 days every June they rehearse together, get coached by Broadway professionals, and then perform on an actual Broadway stage in front of a packed house and a livestream that reaches millions.

And what comes through the screen isn't polish. It's love. These are seventeen-year-olds from Tucson and Atlanta and towns you've never heard of, singing their hearts out—for a lot of them, the first time they've ever stood on a stage like that. Undiluted, un-self-conscious, not-yet-bruised-by-the-industry love for this thing we all do.

It's contagious. You watch it and something in your own chest answers back. Oh, right. I love this too. I have loved it exactly like that.

It's the feeling the Tonys give you on a good year—the plain joy of watching the thing you've devoted your life to get held up in the light, celebrated, taken seriously, wanted. After a decade in the trenches of this business, it's easy to lose contact with whatever it was that pulled you in to begin with. The Jimmys hand it right back.

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The Stakes

The Jimmys have also become a launchpad.

In 2018, Reneé Rapp and Andrew Barth Feldman won the top prizes. Within a year, Feldman was starring in Dear Evan Hansen on Broadway—at sixteen. Rapp went on to Mean Girls on Broadway, then the movie, then an ever-growing pop career. Eva Noblezada didn't even win—she was a finalist back in 2013—and she's since earned two Tony nominations. And that's really only the tip of the iceberg: the list is long.

The pattern is real, and everyone in that building knows it. You don't have to win. You just have to be seen—in that room, on that stage, on a livestream or TikTok or Instagram reel that reaches tens of millions. The Jimmys have quietly become one of the most visible on-ramps to a life in this industry that has ever existed.

Which means the stakes are higher than they've ever been—and not in some abstract, industry way. Picture being seventeen and carrying that. The most pressure-soaked season of a young life already, and now add a Broadway stage, a national broadcast, and the unspoken sense that this could be the thing. The break. The before-and-after.

It isn't an unfounded belief. That's what makes it so heavy. The dream these performers are chasing is genuinely, provably within reach.

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The Second Sensation

Those stakes can also spark something in the viewers that's hard to name.

It's not quite envy—that wanting of what someone else has. It isn't jealousy or sadness either. The closest word for it might be grief.

We talk about grief like it's reserved for the dead. But you can grieve a living thing—a path that forked the other way, a door that closed before you reached it, a version of yourself who never got the chance to walk through it.

The therapist Francis Weller has a name for this. In The Wild Edge of Sorrow, he counts five gates of grief, and the fourth is the hardest to recognize: what we expected and did not receive. It mourns something that never arrived—a loss you can't quite point to, because nothing was taken. It simply never came.

For some, the door was never even a door. The chance came a year too late, or a town too far, or simply never came at all—so there's nothing that was held and then lost, only a threshold you never got to stand at. And watching these performers step through theirs, you can find yourself quietly mourning the one that never opened for you.

That ache, however, is the clearest measure of how much you love: you only grieve what you love. The pride and the grief come from the exact same place—a love for this art form so deep that watching someone else get to live it can crack you wide open. They're the same feeling, seen from two sides.

That's why you can sit there with wet eyes and not know which feeling they belong to. They belong to both.

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The Strange Magic

The Jimmys do in one night what this whole business does over a lifetime.

The love, the longing, the dream held close enough to touch, the watching someone else get the thing you wanted—that's the entire arc of a life in theater, played at ten times the speed. Most of us live it across decades. Auditions we don't book. Roles we watch a friend originate. The slow, ongoing negotiation between how much we love this and what it costs to keep loving it.

The Jimmys take all of it and pour it into three hours on a Monday in June. That is the strange magic of the Jimmys.

Pride, grief, love, and showtunes: who could ask for anything more?

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This week in One Last Thing: the feeling I almost mislabeled this year—and the word that finally let me off the hook.

One Last Thing is for paid subscribers ($5/month), which keeps The Fourth Wall independent and alive. Either way, I'm really glad you're here.