Chapter Text
Michael Bolton listens to his own songs more often than he’d care to admit.
(Not that anyone’s asking, these days.)
These days, he spends most of his time alone. No partner, kids grown, and enough years since his last album that no one’s blowing up his phone about the next tour, the latest sales. He can sleep in, noodle around on his piano, tootle around L.A. in his Lamborghini. Or he can spend the whole day in his bathrobe, streaming his favorite show for the forty-seven-thousandth time, then hop on Bluesky to trade opinions about it via his alt account, with no one around to judge him.
Mostly, retirement rocks.
Still, there are days when he feels like he should be doing more. Putting his celebrity—what remains of it, anyway—to better use. Supporting a cause not only with his ample riches, but with his image; his lyrics; his voice.
Today is one of those days. The silence around his Malibu mansion has grown accusatory, so Michael fires up the Lamborghini and pulls out onto the road, windows down, his own back catalogue on the stereo. He knows it’s a bit Glory Days of him—a bit cringe, as the grandkids would say—but, fuck it. He’s 72 now, and if he’s not quite in his sunset years yet he’s definitely glimpsing them on the horizon, watching the once-massive sky of his life start to purple around its edges.
Plus, he paid for that back catalogue. He paid the price.
Today he’s cued up “Steel Bars,” the one he co-wrote with Dylan. Yeah, a lot of people don’t know that, that Michael Bolton collaborated once with Bob Dylan! That, for two surreal days in 1990, they’d hunkered down in Dylan’s home studio, equipment reeking of the cigarettes Bob still smoked back then. That, in the breaks, they’d talked about growing up Jewish, about changing their names. About dark deals made, bits of themselves they’d given away to get where they’d gotten. Turned out they had a lot more in common than people might think.
Steel bars, wrapped around me
I’ve been your prisoner since the day you found me
I’m bound forever, til the end of time . . .
Fans think that song’s about love, like all of Michael’s big hits were. Well, the fans who’ve ever heard it do. That one never did make it far up the charts—and now, 35 years later, none but the most devoted Boltonheads even remember it.
But that was how it was always going to go, wasn’t it? The terms of the deal. That Michael could fill stadiums forever as long as he churned out the cheeseball power ballads; as long as he kept his head down and kept letting the shit, noxious and buoyant, float to the top again and again.
Have you ever felt like you were treading water, waiting to drown?
Michael pulls the Lamborghini up to the beach and walks out onto the sand. Stares at the Pacific and tries to get his brain to work. That’s why he’s been listening to the old songs again, after all. Not the cheeseball ones—never the cheeseball ones—but the handful of others that he wrote or co-wrote and felt really proud of. To remind himself that he can do this. That he’s done it before.
He's got a pad and pencil in his back pocket. He should pull them out now, try another draft.
He pulls out his phone instead, and texts his daughters.
Have any of you watched it yet? That show I told you about, Our Flag Means Death? I think you’d really like it.
***
It’s not like Michael Bolton has a thing for pirates.
That was just the joke, back in 2011. When he and Samberg and the rest of them had been throwing around ideas for a song, trying to find a wavelength they could all get on—funny enough for the Lonely Island boys, but not too filthy for the Bolton Brand.
Turned out the wavelength was an actual ocean wave. As in the seven seas, and Jack Sparrow. The Scarface bit had been Michael’s idea, but that was it, really. Otherwise, it was the Lonely Island guys’ vision, and their lyrics. He hadn’t written a word.
Which brings us to the problem today.
Michael Bolton wants to write a new pirate song. One song, glory! One song, before he—
Shit, he can’t even think up an original lyric when he’s talking to himself in his own mind.
And therein lies the problem. Because the lyrics to this new song? They’re important. Mission critical, even. These lyrics need to do something, to have an effect on the real world.
They need to get Michael’s favorite show renewed.
Well, that’s the idea, anyway.
His phone pings with Daughter #1’s response.
Omigod
DAD
Daughter #3 quickly follows.
He’s at it again 🏴☠️💀
Daughter #2 enters the chat last.
I actually did watch the first 2 eps
It’s cute, I guess
It's whatever
Michael groans.
2!?! I told you, you need to watch at LEAST thru ep 4 before you decide! A new character shows up, there’s flashbacks, and a clothing swap, and . . . just trust me, OK?
Michael’s finger hovers over the “send” button, but he doesn’t press it. The girls will probably just laugh at him; it’s his usual screed, they’ve heard it before. And if he can’t even convince his own daughters to give the show a fair shake, what chance does he have with the general public? With Hollywood execs? He slides his phone back into his pocket, screed unsent, and pulls out the notepad instead. Flips it open and forces himself to look at the scratch of his own handwriting from the last time he tried to do this.
This is the tale
of Captain Stede Bonnet
Sailing the seas
with one Edward Teach
He’s the Gentleman Pirate
The Brigand of Barbados
Sand in his bits
from when they fucked on the—
Michael slams the notepad shut.
Not the vibe, he tells himself sternly. He’s been reading too much fanfiction, that’s the problem. Got Gentlebeard sex on the brain. Not that there’s anything wrong with having sex on the brain—or with fucking on a beach, for that matter. Michael’s very sex-positive, okay? Walking around with sandy bits is probably some kind of kink, and he doesn’t kink-shame. Not anymore. The fandom has taught him not to do that. The fandom has taught him an awful lot.
That said, the general public probably does not need the explicit-sex-fic versions of the Our Flag crew pitched to them in song. They need, like, a taste of the full OFMD experience! And how can Michael capture the magic of this entire life-changing show in just a few lyrics? The warmth-and-good-food-vibes of it all, in addition to the orgasms? He wants to write a tribute to it, not a mockery. And yet, he also needs to make sure it’s funny and raunchy enough to go viral—to bring in enough eyeballs that it catches the attention of the top brass over at Netflix or Tubi or whatever, and gets one of them to produce a third and final season of his favorite show of all time.
Christ’s oranges, the pressure. It’s too much.
He flips back through a handful of his earlier attempts, all unfinished. Winces at his overhaul of “How Am I Supposed to Live Without You?” redirected at HBO; cringes over the memory of trying to rhyme something other than “graffiti” with “Waititi.”
Finally, he slides the notepad back into his pocket. It's time to admit it: he can’t do this alone. He’s too close to his subject matter, loves it too much. He needs cold-eyed collaborators: Andy, Jorma, Akiva. He’s been thinking that if he came to them with a song already written, it would be an easier yes—but nothing comes easy these days, does it?
(Well, his daughters would probably tell him it could be easy, that he could just use ChatGPT. But the thought of doing that makes Michael vomit in his mouth a little. No, he has standards. He cowrote with Dylan, for fuck’s sake! Generative AI can go gargle his balls. [In a totally non-kink-shamey way, of course.])
The thing is, Michael’s been trying to get in with the Lonely Island boys again—been trying to get a meeting with Samberg for months. Every time, his agent comes back to him full of excuses, just busting at the seams with tales of Andy shooting on location with a schedule packed end-to-end-to-end.
So now Michael’s gonna have to do the thing he never wants to do, and mix business with pleasure. Mix his hopes and dreams with the cast-off faith of his childhood.
In other words: pitch Andy this weekend at the Samberg kid’s bat mitzvah.
It's the social event of the season for L.A.’s Jews, and after pulling just about every string he’s still got left in the biz, Michael has wrangled himself an invitation. The goal now, of course, will be to finagle a minute alone with Andy, ideally in a quiet spot—though Michael knows that may not be possible. So he’ll need to brush up on his moves, too. He envisions himself circling Andy on the ballroom floor, a hora-dancing shark, ready to lunge at the first sign of an opening and go for the jugular with his pitch.
And, hey, maybe Taika will be at the bat mitzvah, too! Because he’s Jewish, right? Or Jewish-ish, at least? Michael expands the fantasy, looping his arm through Taika’s in the hora circle and guiding him up to Andy so he can blow them both away with his idea at the same time. Taika immediately agrees to get back into his leathers for the video; Andy’s already scribbling lyrics on a cocktail napkin. Yeah, it all goes over so well that they throw Michael up on a chair to celebrate, bouncing him high to the tune of Hava Nagila. (Andy’s daughter’s cool with it, she was getting a little chair-sick anyway.)
Hundreds of bat mitzvah guests crowd around Michael now, cheering; he even spots Taika crying a little on the ballroom floor, touched that Michael’s such a big fan. That he’d do all of this just to give the crew of the Revenge a chance at one more outing, one more season . . .
***
Taika’s not at the bat mitzvah.
“Yeahyeahyeah, he was invited,” Jeff Goldblum tells Michael as they stroll from the sanctuary to the ballroom. “But he couldn’t make it because he’s overseas this weekend, shooting some vodka ad.”
Michael seethes. It’s hard to say whether he gets more pissed off about Taika making commercials or Rhys doing yet another voiceover for a kids’ cartoon. How is it that Hollywood still has no fucking idea what to do with these guys?! Rhys should be hosting SNL! Taika should be rolling around in so much indie film financing he hardly knows which of his scripts to shoot first! And, of course, between all that, they should both be back out at sea, swashbuckling and looting and kissing and tearing down every last vestige of toxic masculinity left in creative media. They should be up there in the crow’s nest, Rhys’s face rubbering through a thousand expressions, Taika’s long hair rippling in the wind the way Michael’s used to back before . . . well, before. (And yes, Michael knows it’s a wig. Just let him have this, okay?)
Anyway, Taika’s not there. Andy’s barely even there for the first two hours of the reception, constantly being pulled out of the room for pictures or mobbed by relatives. Michael keeps waiting for the hora to start, but it turns out there will be no hora; this is not that kind of bat mitzvah. The synagogue’s one of those Reconstructionist joints, no rules, and apparently the young Ms. Samberg is much more into Kabbalah than klezmer. The theme of her reception is Oneness With the Universe, so there’s a juice bar instead of an open bar, a meditation guide instead of a DJ.
And even as the guide leads everyone through a series of “relaxing” breath exercises, Michael grows more uneasy by the minute. It’s not just that he hasn’t been able to get within ten feet of Andy yet. It’s not even that he’s clearly been relegated to the geriatric-Jew table (Goldblum, Patinkin, Streisand, etc.), clear across the room from where the Sambergs are sitting with the Stillers and the Portmans and—shit, is that Charlie Kaufman at their table, too?
No, what’s really making Michael uneasy is this space. This building. The sulfur stench of religion permeates it, no matter how Reconstructed its rituals might be. Michael had a loose relationship with Judaism even before the conversation that changed his life forever, that tilted his expectations of eternity on their axis. But ever since that day, that agreement he entered into . . . well. Most of the time, he tries to avoid thinking about it.
Being back in a place of worship like this, though? It’s making him think about it.
A gong sounds, and the pure tone reverberates through Michael’s skull as he feels his dreams of dancing across the room with his project pitch evaporate into thin air. Well, into air that’s actually thick with lavender, because there’s essential oil diffusing now from all four corners of the ballroom. Ah, the irony of breathing the same air as Andy Samberg in a room that smells just the way the fics always describe Stede Bonnet as smelling! Michael turns to Mandy Patinkin, that observation at the tip of his tongue, before he thinks better of speaking it out loud. (He’d hope that the man who brought the world Inigo Montoya would be a fan of OFMD, but he’s been burned by such assumptions in the past.)
He stands up instead. Choking a little on the aerosolized perfume, he slips into the hallway and pulls out his phone. Keeps the event details vague, and posts about breathing lavender-air on his Bluesky alt. But the post gets far less engagement than usual. There’s a big OFMD craft auction going on right now to raise money for trans kids, and most of the fandom’s attention is, understandably, focused on that.
Michael parks himself at the juice bar for the next hour. Turns out there is a single signature cocktail at this shindig, and he downs a series of unholy Manischewitz-kombucha concoctions while he scans the dance floor. Andy’s disappeared yet again. Finally, standing at a urinal in the posh synagogue bathroom for what must be his sixth pee (okay, it definitely is—he’s been counting just so he can say the line to himself at this exact moment), Michael hears someone else step into the room.
“All those Manibuchas go straight through you, don’t they, Mike?”
Michael’s heart stands still. Did he really just hear that voice, saying those words? Or is he so drunk and desperate now that he’s hallucinating? He dares a glance to his left and, yep, there’s Samberg, in the flesh, unzipping at the urinal two spots over.
“Sure does,” Michael says, praying his voice sounds cooler than he feels. Finally, his chance has arrived! There’s no one else in this bathroom; even the tuxedoed hand-towel attendant has mysteriously stepped out. And Andy just basically said a line from the show! The universe is finally on Michael’s side, all the stars of David aligning.
He clears his throat. “Hey, so, Andy. I’ve been thinking—”
But Andy cuts him off. “God, it’s so nice and quiet in here, isn’t it? Though I wouldn’t put it past some of these fuckers to follow me in and try to talk my ear off while I’m having a piss. Can you believe people have been pitching me at this thing? At my own daughter’s bat mitzvah?!” He shakes his head. “It’s fuckin’ . . . kinda gauche, isn’t?”
Michael’s brain reels. Andy’s just said another near-line from the show! Is he as obsessed as Michael is? Maybe he even has a fandom alt—wouldn’t it be hilarious if they were already mutuals on Bluesky? Maybe this is actually going to be a whole lot easier than Michael thought.
“Look,” he starts, “am I hearing you right that you’re—”
But Andy interrupts again. “Like, even Leslie Jones, who I guess wants me to do a cameo in her pickleball movie or something? And don’t get me wrong, I love Leslie! Just, there’s a time and place for this shit, you know? Have your agent call my agent, that’s how this works, am I right?”
Michael, who has been having his agent call Andy’s agent weekly for months now, cringes as he nods in obsequious agreement.
Meanwhile, of course, his brain keeps screaming. Leslie Jones is here? Spanish Jackie Leslie Jones?? How did he miss her? Of course, it makes sense she and Andy would know each other, they both did SNL. Maybe Michael can go back out there and find her in the crowd, team up with her the way he wanted to do with Taika, regroup and ambush Andy, and—
But, no, Andy doesn’t want to be ambushed, especially not by Leslie again. And there’s no guarantee Michael would be able to hunt him down again, anyway—this one encounter has been lucky enough. He needs to make his move now, to slide in sideways with a segue so subtle Andy won’t even know he’s being pitched—something caszh, conversational, unsuspicious—something like—
“Rhys Darby would be so great on SNL!” Michael blurts. “Don’t you think?”
Over the top of the urinals, Andy’s face scrunches in confusion. “What?”
Okay, so maybe that was only a segue in Michael’s mind. Maybe he never actually said any of his previous thoughts about SNL out loud.
Shit.
Still, he can save this. “You know,” he says quickly. “Rhys Darby—the Kiwi comedian? From Flight of the Conchords, and Jumanji, and”—Michael swallows, becoolbecoolbecool!—“oh, yeah, and that really great show Our Flag Means—”
“Ohhh,” Andy cries, cutting him off. “The Conchords guy—yeah, he’s funny! Haven’t seen him in anything for years, though.” He shakes off then, zips up his fly, and is across the room washing his hands before Michael’s even caught his breath.
Wait, does this mean Andy hasn’t seen—hasn’t even heard of—
“Hey, man, thanks again for coming out today.” Michael’s being clapped on the back even as he stands there at the urinal with his dick still in hand. “Really good to see you. Keep well, okay?” Andy shoots Michael finger-guns as he backs his way out of the bathroom.
Fuck.
***
Michael goes ahead and calls a car then, because why stick around? To sample the raw vegan dessert bar? No, thanks. It’s a pint-of-Ben-and-Jerry’s-and-rewatch-“The-Innkeeper”-til-he-cries kind of night.
He only had this one shot, and he blew it.
He climbs into his Uber Black outside the synagogue and rides back out to his tomb of a house, to the stifling Malibu mausoleum where season three of Our Flag Means Death will never grace his private home theater, or his 85-inch Frame, or even his old 60-inch plasma screen. He sulks past all the dark TV sets and opens his laptop instead, first doing his ritual check of the fanvid he posted anonymously on YouTube a few weeks ago. 459 views—that’s only two more than the last time he checked. Maybe the fandom really is shrinking? Either that, or no one new wants to watch an edit of Ed and Stede struggling to be lovers when they can’t be friends.
Michael clicks over to the craft auction instead and pokes around there until he feels better. They’ve raised over $75K for trans kids already—wow, what a fandom! He kind of wishes he could go to one of the cons with all of them, but . . . well, there’s the whole pesky Michael-Bolton-ness of it all. Jackie sure had it right on the show: you amass this much fame and fortune, and you really don’t ever get to be a regular dude again.
Well, hey, maybe Michael can put some of that fortune to good use tonight! The auction is wrapping up, and he’s been meaning to buy something. He swoops in and bids a stupid amount of money for the Act of Grace, bumping the fundraising total up over $90k. He’s sitting pretty atop the leaderboard then, thinking about where in his house he’ll hang the Act (replace the Frame with it, maybe? It really should be as visible as possible, a true conversation piece) when, seconds before the auction closes, some other anonymous rich dickhead outbids him by pennies.
Michael blinks at the screen. What the fuck?! Though, really, it’s his own fault—he should have bid more from the beginning, could have afforded way more! He’s happy for the trans kids, sure, but jeez, some days he can’t even do being ultra-rich right.
He skips the Ben and Jerry’s, and “The Innkeeper,” and drags himself off to bed. His guts are roiling with the litany of today’s failures—or maybe it’s just all those Manibuchas from the bat mitzvah, repeating on him. He’ll sleep badly, he can already tell. Probably have the nightmare again, the one with the red telephone. The one he hadn’t had in so many years he’d basically forgotten all about it until, very recently, it started pinging his brain again.
It's always the same, the nightmare. There’s a red telephone without any markings or buttons on it, like the kind you see at airports on top of the luggage scanners. A direct, emergency landline from the TSA agents to . . . whom, exactly? Michael doesn’t know, but he is sure that that exact type of red emergency phone has been showing up in his dreams of late. It’s always ringing—but whenever he tries to answer, the receiver is so hot he can’t even hold it in his hand, much less get it up to his ear. Can’t ever hear the voice of whoever is trying to reach him.
Michael breathes deep as he climbs into bed and turns out the light, tries to tell his body to relax. His body tells him fuck you, no thanks, then calls him a pathetic loser and kicks him in the nuts for good measure.
It hurts like being kicked in the nuts, at least, feeling as powerless as he does right now. Because he’s rich, yeah—but not finance-a-whole-season-of-TV-just-on-your-own-dime rich. He’s got influence, sure—but not enough anymore to get Samberg to take his calls, much less the heads of the streaming services. And he’s talented, all right—but not enough, apparently, to write a single internet-breaking, queer-pirate-appreciating song all by himself.
It's been a long time since he felt this down and desperate. Not since back in the days when he feared his career would never go anywhere; that no matter what he did, he’d never hit number one. But, then . . .
When Michael finally falls asleep, the red phone is there, ringing in his face, louder than it’s been in weeks.
Fuck it. He’s answering this time.
Dream-Michael grabs for the receiver, gritting his teeth as the red plastic burns his palm. He yanks it to his face and it scorches that skin, too, branding circles on his ear and cheek.
“Hello?” he shouts.
And then, a voice from his distant past—a voice he never thought he’d hear again in all his human years—answers.
You can have it, the voice rasps from down the telephone line. From way, way down.
You can have what you wish for—for a price.