For 10 years, every audition he walks into he’s that guy, Dempsey 1.0, the former Can’t Buy Me Love guy, and who wants that guy? That makes him go, “I’m ugly, I’m untalented, I’m no good, I’m a has-been. It’s like, fuck, what happened to me? I used to be me.”
He even stops going to movies. Because he auditions for so many films and can’t land any, he’s too jealous even to watch them. “I’d come in [to movies] with this bitter attitude,” Dempsey says. “It’s not an escape, because I feel this disappointment, this jealousy.” The projects he does get—Italian independents, Canadian-TV pilots, straight-to-video dreck—sound like the fake ones Vince Chase turns down on Entourage: Bloodknot, Meatballs III, Face the Music. The boy toy becomes the forgotten boy—even worse, the despised boy. In a review of Run, Dempsey’s 1991 mistaken-for-a-mobster farce, People magazine warns its readers to “flee, flee in whatever direction takes you away from the nearest theater showing this movie,” dismissing Dempsey as a “cipher in terms of acting ability and charisma.”
Like so many underemployed actors, Dempsey 1.0 invests in Southern California real estate to augment his SAG income. He buys, remodels, and sells five houses. Pays his alimony. Never has to sell the Porsche 356 he bought with the Can’t Buy Me Love money. Those five houses finance a decade of dues-paying, and there’s even enough left over to cover an auto-racing hobby.
In 1995 he meets his current wife, Jillian, at a hair salon she owns on Melrose Avenue. “He was just a much less confident guy then,” she says now. “I mean, think about the rejection. How many times can you get rejected and kicked around?” Indeed, after the long, steady ego burn of a decade of auditioning and lousy roles and going in for parts he knows he has no chance of winning, Dempsey 1.0 is worn down, defeated, a failure. “I became,” he says, nodding his head, “a regular person.”
Dude, no, not that. Proto to beta to 1.0 to regular person? That’s not how it was drawn up in R&D. Someone call the plant and tell them that if this is 1.0, forget about the later models. We’re done with Dempsey.
But Dempsey is not done with us. He goes back to acting class, learns all that basic stuff like “Listen” and “Let go of the results” and “Be in the moment” and, you know, “Just breathe.”
Then one day, it happens. He turns to his wife and says, “You know what? I don’t give a fuck -anymore.”
Instead of projecting that whining likemelikemelikeme, he begins to emanate the powerfully attractive indifference of those who don’t give a fuck.
He becomes Hollywood’s version of the guy at the bar all the girls like because he doesn’t seem to care if they like him. While every struggling actor in town is desperate to be wanted, Dempsey becomes resigned to being hated. And he thrives on that. The musky “whatever” attitude is irresistible to a town used to hunky men who will drop to their knees for a walk-on role in Cabin Boy II.