The Chilling True Story Of Jesse James Hollywood, The Murderous Drug Dealer From ‘Alpha Dog’

Published July 28, 2025

In August 2000, Jesse James Hollywood kidnapped 15-year-old Nicholas Markowitz because the teenager's brother owed him money, and then orchestrated his brutal murder.

Jesse James Hollywood

ZUMA Press, Inc./Alamy Stock PhotoJesse James Hollywood smiling during his trial for orchestrating the murder of 15-year-old Nick Markowitz.

In August 2000, a group of drug dealers kidnapped Nicholas Markowitz, a 15-year-old high school theater kid who spent most of his time reading. Nicholas Markowitz hadn’t done anything to wrong to upset the dealers — but his older half-brother Ben had.

Ben Markowitz had fallen in with a rough crowd and racked up around $1,200 in debt to a dealer named Jesse James Hollywood. Hollywood and two members of his crew, Jesse Rugge and William Skidmore, had kidnapped Nicholas to use him as leverage to get Ben to pay. But after three days, Hollywood started to get nervous. He found out from a lawyer that if he were to be convicted of kidnapping, he could face life in prison.

Not willing to take the risk, Hollywood made a decision. He offered Ryan Hoyt, who also owed Hollywood a debt, a deal: kill Nicholas Markowitz and his debt would be repaid. Hoyt agreed. He murdered Nicholas Markowitz on Aug. 9, 2000. Three days later, the body of the 15-year-old was found.

Ryan Hoyt was arrested shortly after — and Jesse James Hollywood went on the run.

This is the true story behind Alpha Dog,.

The Feud Between Jesse James Hollywood And Benjamin Markowitz

Jesse James Hollywood was born on Jan. 28, 1980 in the West Hills neighborhood of Los Angeles. By all accounts, Hollywood had a fairly average early life. He played baseball and was recognized as a good reader by his teachers. But he was also troublesome and prone to emotional outbursts, which led to his expulsion in the 10th grade.

Hollywood did end up graduating from a different school nearby, but soon turned to selling marijuana to make money. According to NBC News he was so successful that he was able to afford a huge down payment on a house when he was just 19 years old. Eventually, he looped some of his old friends in on the business too. But the power dynamic was clear — these “friends” were more Hollywood’s lackeys than his high school buddies.

“He would give them a certain amount of pot to sell. And they used whatever neighborhood connections they had to sell it,” Los Angeles Magazine writer Jesse Katz explained to NBC. “And some of them would bring back the money that they earned. And some would come up short. And the ones that came up short became almost like indentured servants to Jesse James Hollywood.”

Jesse James Hollywood In 2000

Santa Barbara Sheriff’s OfficeJesse James Hollywood around the time of the murder.

One of Hollywood’s associates was Ben Markowitz, another troubled teen who, by the age of 15, had already stolen a car, cracked open a kid’s skull with brass knuckles, and spent eight months in a juvenile probation camp, according to reporting from Los Angeles Magazine. He was the polar opposite of his younger half-brother, Nicholas.

Ben’s parents had divorced when he was just four. His father took custody of him at age 12, though by then he was already an “urban legend” in their town, according to his father Jeff.

“My whole life, I was trying to keep Nick from seeing or knowing the truth about Ben’s trouble,” Nick’s mother Susan added. “It was a lot of work keeping them apart.”

But it was impossible to keep their lives separate; despite Ben’s troubles, Nick looked up to his older half-brother. Meanwhile, Ben’s natural inclination toward trouble only worsened when he fell in with Hollywood’s crew. Unlike the others who hung out with Hollywood, though, Ben Markowitz wasn’t afraid to stand up to Hollywood — and things between them got tense, fast.

“Ben was dangerous to Jesse James Hollywood,” Katz explained. “None of the other kids would stand up to him. None of them wanted to fall out of Jesse James Hollywood’s favor. Ben Markowitz just didn’t seem to care… Jesse James Hollywood would tell him, ‘You owe me money.’ Ben Markowitz says, ‘Screw you.'”

Markowitz eventually racked up a $1,200 debt with Hollywood, but he refused to pay. In fact, he made things worse by breaking a window at Hollywood’s house. So Jesse James Hollywood decided he would up the ante too.

Nicholas Markowitz, And The True Story Behind ‘Alpha Dog’

Nicholas Markowitz

ZUMA Press, Inc./Alamy Stock Photo
Nicholas Markowitz was 15 at the time of his murder.

On August 6, 2000, Hollywood and his crew set out to find Ben and settle the score. As they cruised along in their van, they didn’t find Ben. But they did find his 15-year-old brother, Nick. Even though Nick had nothing to do with Ben and Hollywood’s feud, Hollywood saw an opportunity.

Just as in the 2007 film Alpha Dog, in which the character of Johnny Truelove is modeled on Jesse James Hollywood, Hollywood and his crew hopped out of their van, roughed Nick up, and then threw him inside.

But as Katz explained, it didn’t seem to Nick that he was in immediate danger. When his captors found Valium and weed in his pockets, they let him have some, almost like he was part of the party. Though Nick was briefly bound with duct tape and gagged with a sock, he was soon after freed and allowed to smoke weed, drink gin, and play a video game.

According to former Santa Barbara county chief deputy sheriff Bruce Correll, Nick Markowitz did not think he was in any danger. Nick even reportedly told his captors, “This will be a story I can tell my grandchildren.”

The first 36 hours weren’t as relaxed for Nick Markowitz’s parents, however. They frantically tried to reach anyone who knew Nick to figure out where he had gone. When they finally got in touch with Ben, he told them that he had not heard from Nick either. At that point, they notified the police.

Jesse Rugge

ZUMA Press, Inc./Alamy Stock Photo
Jesse Rugge testifying about his role in the kidnapping and murder.

In fact, no one except Jesse James Hollywood seemed to realize the gravity of the situation. While members of his crew bounced Nick around from house to house, entertaining him with video games and pool parties, and assuring him that they’d be taking him home, Hollywood was “tripping out,” as witness Jesse Rugge would put it.

Hollywood hadn’t stuck around after the kidnapping. He had gone home to meet with his family’s lawyer, who informed him that being found guilty of kidnapping could land him in jail for the rest of his life. Now, he was conflicted. If he kept Nick Markowitz hostage, he could get in serious trouble; the same could be said if he let Nick go and Nick told someone what happened.

Jesse James Hollywood decided the only way out was to murder the 15-year-old.

Nicholas Markowitz’s Murder Sends Jesse James Hollywood On The Run

Graham Pressley

ZUMA Press, Inc./Alamy Stock Photo
Graham Pressley tearful during his trial.

Not wanting to get his own hands dirty, Jesse James Hollywood decided to leverage his friend Ryan Hoyt’s debt. He enlisted him to kill Nick in exchange for calling their debt even.

Hoyt was something of a punching bag in the group. He had had a rough life, with an alcoholic mother, a heroin-addicted sister, an abusive father, and a younger brother in prison for armed robbery. He spent most of his time at Hollywood’s place, trying to stay in his good graces. And when Hollywood suggested a way to clear his debt, Hoyt agreed to kill Nick Markowitz.

On August 9, 2000, Hoyt picked up Nick — but not to take him home.

Instead, he took him — along with Rugge and another friend named Graham Pressley — up along the Lizard’s Mouth trail in the Santa Ynez Mountains. There, with Hoyt holding a TEC-DC9 semi-automatic handgun, they taped Nicholas Markowitz’s mouth shut. Hoyt struck him with a shovel, and when he fell into the shallow grave they had dug for him, Hoyt shot him nine times.

Ryan Hoyt

ZUMA Press, Inc./Alamy Stock PhotoRyan Hoyt during his sentencing.

Three days later, Nicholas Markowitz’s body was found. Hoyt, Rugge, Pressley, and Will Skidmore, who had helped kidnap Nick originally, were arrested on charges of kidnapping and murder. Hoyt was ultimately convicted in November 2001 and sentenced to death, though his sentence later commuted to life in prison in January 2024. Rugge, meanwhile, was acquitted on the murder charge, served 11 years in prison, was released on parole in 2013.

Skidmore was sentenced to nine years in a state prison as part of a plea bargain, released in 2009, and Pressley, 17 at the time and the youngest of the kidnappers, was convicted of second-degree murder and held at a youth facility until he turned 25 in 2007. He has since been released.

But where was Jesse James Hollywood, the man who had orchestrated the killing in the first place?

It would be another five years before Hollywood was found in Rio de Janeiro under the assumed name of “Michael Costa Giroux.” He had learned Portuguese and claimed to be a native of Rio, living off a $1,200 stipend from his father and various odd jobs. Meanwhile, he had become one of the youngest people to ever appear on the FBI’s Most Wanted list, with a reward of $50,000 for information leading to his capture.

Rock Etching At Nicholas Markowitz Murder Scene

Brian Vander Brug/Los Angeles Times/Getty ImagesA monument to Nicholas Markowitz at the site of his murder.

Jesse James Hollywood was finally arrested in 2005, two years before the film about the kidnapping and murder of Nicholas Markowitz, Alpha Dog, came out. After a long trial and series of testimonies, Hollywood was found guilty of kidnapping and first-degree murder with special circumstances, and ultimately sentenced to life in prison.

Both he and Hoyt remain imprisoned to this day.


After reading about Jesse James Hollywood and the killing of Nicholas Markowitz, read about Brendan Dassey and his controversial sentencing for the murder of Theresa Halbach. Then, read about Erin Caffey, the teen who convinced her boyfriend to murder her family.

author
Austin Harvey
author
A staff writer for All That's Interesting since 2022, Austin Harvey has also had work published with Discover Magazine, Giddy, and Lucid, covering topics including history, and sociology. He has published more than 1,000 pieces, largely covering modern history and archaeology. He is a co-host of the History Uncovered podcast as well as a co-host and founder of the Conspiracy Realists podcast. He holds a Bachelor's degree from Point Park University. He is based in Pittsburgh, Pennsylvania.
editor
Kaleena Fraga
editor
A senior staff writer for All That's Interesting since 2021 and co-host of the History Uncovered Podcast, Kaleena Fraga graduated with a dual degree in American History and French Language and Literature from Oberlin College. She previously ran the presidential history blog History First, and has had work published in The Washington Post, Gastro Obscura, and elsewhere. She has published more than 1,200 pieces on topics including history and archaeology. She is based in Brooklyn, New York.
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Harvey, Austin. "The Chilling True Story Of Jesse James Hollywood, The Murderous Drug Dealer From ‘Alpha Dog’." AllThatsInteresting.com, July 28, 2025, https://allthatsinteresting.com/jesse-james-hollywood. Accessed July 29, 2025.