The hair show led to steady modeling gigs through an agency out of Atlanta. After a year at the University of Georgia, an agency in New York City tracked him down and promised him better work. Holloway jumped a Greyhound quicker than you could say “Day-uhm.” A little friend-of-a-friend networking later, he found a place to crash in Queens with a bunch of metalhead brothers into beer, Megadeth, and Metallica. With the help of a fake ID, he got a job tending bar in the East Village at what’s now Lucky Cheng’s.
But in the late eighties Holloway’s pretty-boy androgyny was decidedly out. His agency suggested he go to Europe and “get some age on him.” So the wide-eyed bumpkin partied around the Old World for a few years until finally landing the cover of French Vogue. He was still broke, but at least he was famous. “It was everywhere,” he says. “All over Paris. Huge billboards. Buses. And I’m so poor I can’t even buy the son of a bitch.” That changed real quick. Next up came the cover of a little magazine called Details. Ads for Perry Ellis. Versace. His career as a clothes rack took off. But instead of blowing it, he took the $120,000 he was clearing annually and invested in a land-development company back in Georgia. A few years later he and his then-girlfriend became silent partners in the Los Angeles branch of the fashionable Indochine restaurant. Transitioning from modeling to moguling seemed to come naturally to Holloway; but he was guarding a secret: He wanted to act.
“Everyone was like, ‘You’re a model—now you can go act.’ And I’m like, ‘Fuck you,’” Holloway says. “I mean, I wanted to, but I was afraid of being a cliché.” Turns out the only thing clichéd about his thespian dreams was his abject failure. In eight years he appeared in bit parts on CSI and Walker, Texas Ranger and was killed on the first episode of Angel. Those were the highlights. The rest was a mix of aborted pilots (My Roommate Is a Big, Fat Slut—seriously) and eye-gougingly bad indies like Dr. Benny, a “gynecological comedy.” By 2004 he’d given up. Losing the role of Charles Ingalls in ABC’s Little House on the Prairie miniseries in a last-minute switcheroo was the final, crushing blow.
So he got his real-estate license. And if not for a last-gasp fax—a casting for some show about strangers on some spooky island—we might be talking about the best-looking Coldwell Banker rep in history. Still, it was a long shot. ABC, having seen him read for the Ingalls role, didn’t think Holloway could pull off Sawyer, who at this point was written as a slick, Prada-wearing gangster. “I wasn’t the dark horse,” he says. “I wasn’t even in the running.”
Pissed off, tired, his balls on the line, Holloway showed up for his reading with series creators J.J. Abrams and Damon Lindelof in a thermal and jeans and chewed through his lines like an angry gator. But while ripping into a chunky piece of dialogue, he blanked. And at that moment, all the frustration of eight years banging that pretty little head against the wall balled itself up into Holloway’s booted right foot. Crack! He punted a folding chair across the room. Abrams and Lindelof scrambled for cover. “Don’t hit me,” Abrams pleaded. “I ain’t gonna hit you,” Holloway hissed. And in that combustible few seconds, Sawyer was more or less born. Break out the leis.