It’s hard to say what The Gambler is up to: daring Mark Wahlberg vehicle? Bored studio remake? Still, it’s more notable for what it isn’t: a Leonardo DiCaprio movie.

More interesting yet: This is the second time DiCaprio has been in the news about a Wahlberg movie this month. The Sony leak refreshed the page on an oft-repeated rumor: that for Mark Wahlberg to land Boogie Nights, something else had to happen first. Leonardo DiCaprio had to pass.

Here’s the question, though: What if he hadn’t?

1996

Leonardo DiCaprio is being offered the role of Dirk Diggler. For DiCaprio, 22 and a rising star, this makes all the sense in the world: directing the offering is Paul Thomas Anderson, up-and-coming director par excellence. The script — for a film called Boogie Nights — is lean yet sprawling, classic but modern. The part is complex and sexual and starry and strange. In other words: It’s adult. DiCaprio signs on without thinking twice.

Around this same time, James Cameron is looking to cast Jack, the male lead in Titanic, his mega-budget historical epic. DiCaprio, coming off Romeo + Juliet, and at rarefied levels of peak heartthrob, is his first choice. Cameron gives him a call. “Leo, baby, do Titanic.” (Is that how directors talked in 1996? Let’s absolutely say it was.) Leo wavers. The lead in Titanic is a giant opportunity, but isn’t Jack just, you know, Romeo on a boat? Dirk Diggler is a young De Niro part; it’s a Man’s Role. Leo is a young De Niro; he’s a Man. The logic is too compelling to ignore. He turns Cameron down.

Snubbed by DiCaprio, Cameron moves on to the second name on his list: Mark Wahlberg. At 25, he might be a little old for Jack, and at Mark Wahlberg he might be a little Mark Wahlberg, but who knows? Maybe DiCaprio was too pretty or young to begin with. Jack’s a romantic, sure, but he’s also a hustler, a scrappy hero who finds a way. Cameron gives him a call. “Marky, baby, do Titanic.” Wahlberg can’t believe it. He’s gotten offers since Fear hit, but this is James Cameron, the director of Raging Bull. Of course he says yes.

1997

20th Century Fox

Titanic is — you’re not going to believe this — a hit. Wahlberg nails it, which is to say he memorizes his lines. The rest — “Draw me like one of your French girls,” “You wanna go to a real party,” Winslet, Bates, BILLY ZANE, f/x budget, ’90s tweens, the old economy, puberty, “I’m the king of the world” — takes care of itself. Only the ending has to be slightly adjusted. With Wahlberg too athletic-looking to drown, Cameron tweaks the script so that Jack, after kissing Rose tearfully good-bye, whispers, “Swimming is fucking easy,” and then front-strokes to shore. Everyone loves it. A reworked version of “My Heart Will Go On” plays over the end credits, with Celine Dion singing “Near, far, wherever you are / that’s what’s up.” The movie wins Best Picture at the Oscars — and, with Jack alive, spawns 10 sequels. (2 Ti 2 Tanic and Tritanic with Cameron & Wahlberg; Bad Cruise, Fivetanic, Ti 6, Tanic, Bad Cruise 2, Ninetanic, Titenic, and Boat without them. The franchise ends in 2008 after Boat — tagline: “Do you like boats?” — underperforms.) It’s 1997. Mark Wahlberg is the biggest movie star in the world.

New Line Cinema

Boogie Nights is — you’re going to believe this — not a hit. DiCaprio struggles through it. Nothing in his performance is ever quite right: nervy instead of meaty, acted instead of reacted, striving instead of fucking. The talent is there but in all the wrong ways. Boogie gets mixed reviews and goes down as an admirable miss. Audiences agree that the final scene, wherein DiCaprio (who refused prosthetics) pulls a San Pellegrino bottle from his pants and drinks it, is a letdown. 

Interlude

Titanic should have been called Boogie Nights and Boogie Nights should have been called Titanic, please agree, thank you.

1998-2001

DiCaprio’s Romeo heat wanes as Hollywood tries on other heartthrobs — Damon and Affleck post–Good Will Hunting, Wahlberg post-Titanic. DiCaprio’s Boogie Nights performance wins him a new set of fans. David O. Russell, 1998: “The San Pellegrino at the end. Brilliant scene. I have a theory that movies are fake.” James Gray, also ’98: “I see Leo in Boogie as really two distinct performances: almost as brothers, on opposite sides of the law. I’m a better director than writer.”

DiCaprio decides there’s virtue in working with those who seem to see something in him, and signs on for a pair of projects with emergent auteurs: Three Kings with Russell, followed by The Yards with Gray. In the former he ends up overshadowed by prime George Clooney, and in the latter he ends up overshadowed by movies that people watch. A pivot toward the mainstream leaves Leo no better off: critically savaged (Planet of the Apes), everything savaged (Rock Star), Clooney’d again (The Perfect Storm). He is an actor that people want to work with, and, in the right circumstance, a leading man. But he’s not a star.

Andrew Savulich/NY Daily News Archive via Getty Images

Mark Wahlberg is a star, but he’s not an actor. 2 Ti 2 Tanic is as much a critical bomb as it is a commercial hit. Wahlberg’s performance earns near-total derision — particularly his attempt to turn “71 percent of the Earth is water; the rest is my fist” into a catchphrase, repeated throughout. Tritanic is more of the same — the franchise’s best from a box-office perspective, worst from every other. The film’s climax — a talking iceberg saying “Just the tip … ” before killing everyone — results in an emergency congressional hearing to revoke Titanic’s Best Picture Oscar. The votes aren’t there, but Wahlberg and Cameron bow out of future installments.

2002 

Humiliated, Wahlberg admits that it’s time for a change. He’s 30; like Prince William told him after a quiet threesome in ’01, “No one’s an idol forever.” The blond hair (frosted tips from Titanic — kept it), the blue eyes (who knows?) … what are they for? They’re not his. That’s not art. You know what is art? Doing arty movies and saying smart-sounding shit in interviews. People love that. They respect it. You know what part he could have done? That porno movie that everyone hated from the ’90s. With DiCaprio. Why couldn’t he make one of those? He would have killed that role. Fuck James Cameron’s Oscar. Where’s Mark Wahlberg’s Oscar? It’s acting. You just … do it, or whatever.

Chris Polk/FilmMagic

This literally turns out to be true. Not for anyone, of course, but specifically Wahlberg: He really can act. His agent scores him a screen test for Gangs of New York, the new Martin Scorsese picture. It’s a favor, nothing more. Wahlberg walks into the room and stands and delivers, using the only acting method he knows: making sounds with his mouth and movements with his hands. He nails it. Scorsese looks him in the eye and breaks the silence: “Marky, baby. I need you in this part. I need you in every part now. You’re my muse.” Wahlberg can’t believe it. This is Martin Scorsese: the director of The Godfather. He signs on for the movie. They make it Gangs of Massachusetts. Everyone loves it. Fuck everyone. It’s Oscar time.

2002 

It’s 2002, five years past Boogie Nights, and for DiCaprio stardom feels further away than ever. He is a tweener: too art-house for the mainstream, too mainstream for the art house. There are no good offers. His prospects, once so promising, seem grim. But then John HBO, the president of HBO, calls him, and everything changes. 

HBO’s pitch gets right to the point: Leo wants a good role, and Leo wants to be a movie star. Well, what better way to become a movie star than to play a movie star? It would be a weekly series on HBO. DiCaprio as Vincent Chase, an actor trying to make it in Hollywood. It’s perfect. Chase’s M.O. is unwavering and beautiful: live the dream, hang with friends, and become not just a movie star but an idealized version of Leo’s vision for himself.

He says yes, contingent on three demands. The first is that they cast his real-life friends in support: Tobey Maguire as his older brother, Kevin Connolly as his best friend, and Lukas Haas as the fourth guy. “Yeah, we don’t care,” says HBO, and so it comes to pass.

Dimitrios Kambouris/WireImage

Second, that the show have no conflict whatsoever, and each episode end with Leo’s Chase getting what he wants. “Yeah, we don’t care,” says HBO, and so it comes to pass.

Third and finally, that they name the show after his friends’ real-life moniker for themselves: Pussy Posse. “How about Posse,” says HBO, and so it comes to pass. Posse: Sunday nights at 9 on HBO. Starring Leonardo DiCaprio.

2003-05

It’s a hit. A huge, absurd, tensionless, nudity-filled hit.

People love it. And just like that, Leonardo DiCaprio gets what he wants: a good role, and to be a star. Well, almost. He doesn’t want to be a star. He wants to be a movie star.

J. Vespa/WireImage for Bragman Nyman Cafarelli

Winning an Oscar is hard. Mark Wahlberg would know. He’s been snubbed by voters twice in ’02 — first for Gangs of Massachusetts and then again for Spielberg’s Yo, Catch Me. His desire to win one has upgraded steadily to obsession. In 2004 he does another Scorsese. This time: The Aviator, the story of Howard Hughes. It’s a biopic. It should be like shooting awards in a barrel. He misses the barrel. Scorsese, Spielberg, Scorsese: nothing, nothing, nothing.

2006

There is only one genre more Oscar-friendly than the biopic: the gangster pic. The Departed, in ’06, is Wahlberg’s best chance at winning Best Actor yet. He’s playing Billy Costigan, an undercover cop attempting to infiltrate the Boston Mob. A movie star playing an actor playing a cop playing a criminal. Scorsese behind the camera again. This is it.

DOMINIQUE FAGET/AFP/GettyImages

Scorsese calls Leonardo DiCaprio and wastes no time. He’s prepping his new movie, The Departed, and has one role left to cast: Dignam, a tough cop with a smart mouth and a survivalist gene. It’s not the biggest part, but it might be the best. “Love you in Posse, Leo. Love. The whole show. Can’t get enough of it. That scene where you make out with the tiger on the yacht? The one where it turns out the chess pieces are cocaine? I could kiss you. Haven’t watched a movie in two years. All I need are my Posse DVDs.” Leo says yes before Scorsese finishes the sentence. “Are you sure?” Scorsese asks. “You can take a day if you want. I know the shooting schedule over at HBO … ” DiCaprio cuts him off. “It’s not HBO. It’s TV.”

2007

The Departed is a wild success. So wild that someone wins his first Oscar for it. It’s not Mark Wahlberg.

Accepting his Best Director Oscar, Scorsese gives what many later call an unusual speech: “Thank you. Wow. This is … just, wow. It’s like in Season 2 of Posse, when Vince wins the Oscar, then joins the Brazilian modeling clique. Thank you. Wow.” Another big winner that night is Leonardo DiCaprio, also for The Departed, receiving his first nomination, for his role as Dignam.

2008-13

Getting snubbed for The Departed sends Wahlberg over the edge. He needs that Oscar, that confirmation, that number on the board. He’ll do anything. He does anything.

The next five years are, at best, a blur: a pander to Titanic nostalgia (Revolutionary Road), another Scorsese (Shutter Island), another biopic (J. Edgar), even a showy supporting role (Django Unchained). Eventually his pursuit comes to a blinding head: a remake of The Great Gatsby, starring Wahlberg as Gatsby. It’s a really good part, but an awful part for him, like an expensive tuxedo that doesn’t fit.

Gatsby tanks at the box office, done in by a brutal trailer in which Wahlberg (tips frosted again) sings an acoustic cover of “Empire State of Mind.” The performance is as bad as feared. The reviews are merciless. Wahlberg does win something, though: Worst Actor at the Razzies. On the eve of the Oscars, he calls his agent: “I’m retired.”

Noel Vasquez/Getty Images

Posse is the most popular television show in the world. The fifth season’s finale, which ends with Vince buying a helicopter that fits into the tip of his penis, becomes the highest-rated episode in the history of TV.

Once again, DiCaprio wins the fandom of emergent auteurs: this time Seth MacFarlane and Michael Bay. He stars in Ted for MacFarlane, and is funnier than expected. He stars in Pain & Gain for Bay, and shows surprising action chops. They aren’t Leo Roles, exactly, though perhaps that’s the point.

It’s 2013. Leonardo DiCaprio is a movie star. 

2014

Scorsese is gearing up for his next film, and it’s a good one: a modern-day remake of 1974’s The Gambler. The script, by Departed writer William Monahan, is crackling. The part, in James Caan’s footsteps, is iconic. The director gives Wahlberg a call. Voice mail. “I’m retired. If you’re a model and want to date, leave your name at the beep.” Scorsese is heartbroken, but he has no choice. There’s a movie to make. He looks at his list’s second name.  

“Leo, baby, it’s Marty.”

2015

Leonardo DiCaprio’s phone is ringing. It’s John HBO. HBO congratulates him on his Best Actor Oscar, tells him he loved The Gambler, and that they finally have the juice to do what they should have done years ago: make Posse: The Movie.

DiCaprio says no. “Sorry, John,” he tells him. “But I’m just not Vince anymore. I’m Leo. I’m a movie star.” Before hanging up, he suggests P.T. Anderson — a nice, talented guy who hasn’t worked in 18 years — to direct.

GABRIEL BOUYS/AFP/GettyImages 

Anderson is relieved. Posse is fine, and after decades in director jail he’s glad to make movies at all. But Leonardo DiCaprio — whom he still blames for Boogie Nights, and maybe ruining his life — is not the actor he wants to make it with. He opens his laptop and types an email. 

“Hey, Mark, Paul here. Heard you’re retired, but I want you to star in Posse for me. My whole career, I have one regret: not casting you in Boogie Nights. P.S. Fuck everyone, and fuck the Oscars.” Wahlberg signs on the next day.

The movie is now set — with a minor change. Absent DiCaprio, the name Posse presents licensing issues. The producers call an emergency meeting to think of a new one. “What about Bros?” asks HBO. “How about Friendship,” suggests Anderson. “Nah,” says Wahlberg. He puts on his sunglasses and takes off his shirt. “We’ll call it Entourage.”

Sam Donsky (@danceremix) is a writer in Philadelphia.