When Miley Cyrus was just 16 and starring in the hit show Hannah Montana, she was already a household name.
But with fame often comes unwanted attention — and for Miley, that attention turned frightening.
One man’s obsession with her spiraled out of control, eventually leading to arrests, a restraining order, and deeply disturbing behavior.
This chilling story recently resurfaced in Hollywood Demons — an Investigation Discovery docuseries — in an episode titled Stalking the Stars, which dives into the frightening series of events involving her alleged stalker, Mark McLeod.
The First Arrests and a Delusional Romance
Back in 2009, Miley was in Savannah, Georgia, filming The Last Song, when McLeod, who was 53 at the time, made his first attempt to approach her on set. He was arrested after trying to breach security and returned just weeks later, prompting a second arrest. That time, police say he claimed he and Miley were actually engaged.
According to reports, McLeod insisted she had accepted his marriage proposal 18 months earlier and even claimed that her father, country singer Billy Ray Cyrus, had given their relationship his blessing. Needless to say, none of that was true.
A Sister Speaks Out About the Warning Signs
Mark McLeod’s sister, Larilyn Adair, spoke candidly in the episode, reflecting on the bizarre and disturbing behavior her brother began to show.
She admitted that, at first, there weren’t any clear red flags — at least until he told her he wanted to marry Miley.
“He was always into music,” she explained. “He was in a fan chatroom with someone he thought was Miley, and somewhere along the line, he convinced himself he was really talking to her.”
That belief, however delusional, quickly became dangerous.
Larilyn described how her brother pawned his beloved guitar, used the money to buy a ring, and mailed it to Miley.
She was alarmed but didn’t yet realize the full extent of how far he was willing to go.
Stalking Escalates to Physical Pursuits
Larilyn shared that McLeod didn’t stop at online fantasies — he started following Miley in real life.
Friends told her he camped out in his car, traveled to multiple concerts, and even snuck into campgrounds to use showers.
At one concert, Larilyn said Miley made eye contact with the crowd — and McLeod took that as a personal sign.
“She looked at the crowd, and he thought she was looking at him,” she recalled.
That moment seemed to feed his obsession. He tried to sneak onto her tour bus afterward and had to be escorted away by security — more than once.
A Book Signing Becomes Another Attempt
McLeod’s fixation didn’t fade. He followed Miley to a book signing in New York City where he was first in line, captured on camera telling reporters he was nervous to see her “face to face.”
According to his sister, he proposed to Miley at the event.
“He told me later that she said, ‘I’m flattered, thank you so much for the flowers,’ then she signed his book and he left.” But this encounter only seemed to intensify his behavior.
Final Arrest Near the Set of The Last Song
Just three months later, McLeod showed up again — this time on the set of The Last Song.
He was caught trying to get close to Miley once more, arrested again, and charged with disorderly conduct, obstruction of justice, and stalking.
After his arrest, he made a chilling comment to the officers: “No one will be able to keep us apart.”
He even claimed the arresting officer would be invited to his and Miley’s wedding.
Ultimately, McLeod pleaded guilty to resisting arrest.
The more serious stalking charges were dropped — but the impact of his actions lingered for Miley.
The Cost of Fame and the Importance of Boundaries
Now 32, Miley has never spoken publicly in great detail about the ordeal, but this documentary episode serves as a stark reminder of the dangers celebrities — especially young women — can face from obsessive fans.
What may begin as admiration can sometimes evolve into something far more frightening.
While Mark McLeod was never convicted of stalking, his relentless pursuit, delusional claims, and disturbing behavior left a lasting mark on a teenage star just trying to live her dream.