Colin Farrell is one of the biggest actors in Hollywood, but his road to stardom is far darker than most people realize. From his spiraling addictions to his bizarre love life, Farrell has the most messed-up story imaginable.
1. He Came From Nothing
Despite being one of Hollywood’s lead actors, Colin Farrell came from very humble beginnings. Growing up in Castlerock—a middle-class suburb in Dublin—Farrell felt something missing in his household.
Starved for culture, the young boy wished for more music and theatre in his life. He had no clue what the future held, or just how turbulent it would prove to be.
2. He Almost Joined A Boy Band
Though destined for acting, Colin Farrell almost became a part of the boy band Boyzone. Key word: almost.
While dancing at a nightclub, he caught the eye of music manager Louis Walsh. Decked out in a rubber t-shirt and leather pants, Farrell seemed like the perfect fit for Walsh’s latest project.
He said, “I’m getting this band together and it’s gonna be great, and you’d be wonderful”. This sounded like an unbelievable opportunity—but there was one huge problem.
3. He Couldn’t Sing
You see, though he certainly had the moves and the dashing looks, Farrell couldn’t sing to save his life. However, bolstered by Walsh’s belief in him, he arrived at the open auditions completely confident that he’d land the gig. Boy was he wrong.
When Farrell opened his mouth to sing “Careless Whisper,” he stunned everyone—and not in a good way.
4. He Humiliated Himself
Later, when reminiscing about this cringeworthy audition, Farrell confessed, “Terrible tune coming out of this mouth, murdered it”. In fact, he was so terrible, the judges asked him to sing it again, perhaps hoping that he’d just had a bad run-through. Nope.
Later that night, Louis Walsh had to swallow his promises and break the bad news to Farrell: It just wasn’t going to happen. But this wasn’t the last bump in the road for Farrell.
In fact, when he was 18, his life took a startlingly dark turn.
5. He Was A Wanted Man
Colin Farrell was completely shocked when authorities took him in for questioning for the most bizarre reason. He was a suspect in an attempted murder case.
When shown a photo of the guilty man, Farrell couldn’t believe his eyes. The man in the photo did look exactly like him. The similarities shook him to the core: “[The suspect] had bushy eyebrows, a mole on his face, spoke even in two dimensions with an Irish accent”. But that wasn’t the craziest part.
6. He Had A Creepy Doppelganger
Farrell’s doppelganger had done some truly heinous things. He’d beaten a man and discarded him in his apartment, and then proceeded to light the place on fire, leaving the victim to endure an agonizing demise.
When Farrell saw how much he looked like the deviant in question, he knew he was in deep trouble—and not just because of the physical similarities.
7. He Blacked Out
Farrell had blacked out on the night in question, which only freaked him out more: “…I wondered, ‘Could I have done such a thing?’”
While being held by the authorities for six brutal hours, Farrell only felt one overwhelming emotion—fear. However, a lucky twist of fate came to the rescue.
8. His Friend Saved Him
Turns out, there was a good reason why Colin Farrell had blacked out: He had been high as a kite with his friend. Thankfully, his friend had journaled about their wild night out, therefore providing Farrell with a much-needed alibi. However, when it came to real-life nightmares, Hollywood had an arsenal reserved just for him.
9. He Had Every Opportunity
Colin Farrell’s rise to stardom was incredibly swift. Though he started his career in television, it only took him a couple years to crack Hollywood. At the start of the 2000s, he starred in box office successes like Phone Booth and Minority Report. But behind the scenes, his lifestyle began spiraling out of control.
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10. He Partied Hard
With great fame comes great power—and Farrell wielded his with fierce abandon. He began using his money and clout to chase down pleasure in all its forms. He once said, “There were a lot of parties in hotel rooms all around the world. For years and years I ran up massive hotel bills and I just lived to the full”. But his actions had dire consequences.
11. He Had Dangerous Addictions
You see, Colin Farrell had a dangerous secret. Since the age of 13, he’d turned down the dark path of drinking.
In the beginning, he’d sneak around his parents’ home as a young teen, breaking into their drinks cabinet. After that, he began sharing cans with his friends in the fields. But upon walking into a pub for the first time, that’s when everything changed.
12. He Frequented The Wrong Home
Farrell truly felt at home in a pub with a drink in his hand, and this only opened him up to a world of other vices. As time passed, the youth’s tolerance for illicit substances steadily increased.
Eventually, fame would only make it easier for him to indulge in these risky habits—but even as a teen, his addictions pushed him right to the very edge.
13. He Was Self-Destructive
At the peak of this reckless behavior, Farrell admitted that his lifestyle was bound to drive him to an early grave. When he was only 19, the extent of his self-destruction became abundantly clear—and he decided to seek out some help.
He visited a therapist, who told him to write down everything he was doing in a single week. But, upon reading Farrell’s astounding list, his therapist had a chilling response.
14. He Struggled With Depression
Colin Farrell’s therapist just looked at him and said, “And you wonder why you’re depressed?” Though he managed to stay clean for half a year, this was only the start of a long and painful road.
Sadly, Farrell's sobriety didn't last long. Not only was he disappearing down a rabbit hole, but Farrell’s fiery tongue was also getting him into a lot of trouble.
15. He Was A Hellraiser
By 2003, Farrell had cemented his reputation as a Hollywood hellraiser, and his controversial statements weren’t helping. In one interview, he openly talked about how he thought it was okay to use substances “in moderation” and even compared paying for intimacy to ordering a pizza.
He was living the high life, but it was all about to come crashing down.
16. He Had The Role Of A Lifetime
Colin Farrell thought he’d hit the jackpot when he landed a role in Alexander the Great—but little did he know, it would eventually become his worst nightmare.
To Farrell, the role of Alexander seemed powerful and he had complete faith in the strength of the script. What’s more? As rumor has it, he even got cozy with one very beautiful co-star.
17. He Had A Steamy Affair
Not only did Farrell star in what he assumed would be a successful blockbuster, but he also rubbed shoulders with the alluring Angelina Jolie, who played his mother, Queen Olympias. Rumors abounded that Jolie was completely entranced by Farrell and even had a fling with him throughout filming.
And the speculation didn’t end there.
18. He Was Her First Choice
Shockingly, some believed that Angelina Jolie only turned to Brad Pitt because Colin Farrell didn’t want to pursue a relationship with her. But whatever the truth may be, by the time the film hit theaters, Farrell had a more pressing disaster on his hands—one that almost destroyed his career forever.
19. He Was Too Confident
Throughout filming Alexander the Great, Farrell truly believed that he was working on a masterpiece. He and the rest of the crew wholeheartedly believed that they’d be bringing home awards after its release. But they couldn’t have been more wrong.
The second he started reading reviews of his performance, Farrell felt his world cave in.
20. He Was A Total Failure
Alexander the Great was one big failure—and Colin Farrell was at the center of it. Critics were out for blood.
They called him, “Alexander the fool,” “Alexander the bore,” “Alexander the incomprehensible,” and “Alexander the weakling”. As the vicious reviews rolled in, Farrell felt an unbelievable amount of shame—and it almost drove him to a harrowing act.
21. His Shame Drove Him To The Edge
Farrell took his film’s failure to heart and even contemplated taking his own life. He said, “I remember thinking that I’ll go to New York, buy $2,000 worth of smack and rent a bedsit, put black sacks on the window and shoot up until I die”.
For a while, the studios didn’t want to touch Farrell—and sadly, his life was about to get worse before it got better.
22. His Ex-Girlfriend Betrayed Him
In 2005, Farrell’s past came back to haunt him in a scandalous way. His ex-girlfriend, American model Nicole Narain, released a very revealing tape of Farrell and her getting intimate with one another. He believed that she’d pulled this nasty stunt to make money and hurt his acting career.
Horrified by this exposure, Farrell retaliated.
23. He Refused The Money
Farrell sued Narain for publicly distributing their tape without his consent. He was even offered $5 million for its rights—but the actor had a very good reason for refusing the money.
He told Elle, “I was deposed for four hours explaining why I didn’t want it to be released. God forbid, it’s an on-demand movie in a hotel room and my mother says, ‘Oh, I haven’t seen this work of my son’s,’ and hits purchase”.
But as it turned out, this tape was the least of his worries.
24. He Couldn’t Remember
By the time he’d finished filming Miami Vice in 2005, Farrell was circling the drain. While attending the premiere the following year, he had a horrifying revelation.
He realized that he’d completely blacked out during most of the production; he couldn’t remember acting in many of his scenes. But that wasn’t all.
25. He Lost Control
2005 was the year Colin Farrell finally lost control. On reminiscing about his addictions, he said, “…I knew I couldn’t stop and I wasn’t going to stop…I crossed the line and couldn’t get back on my own”.
When he finally checked into rehab, Farrell faced his painful history for the first time—and the process caused him to completely break down.
26. He Cried Like A Baby
In rehab, Farrell wrote down every bad decision he’d ever made since the age of 13—every substance he’d subjected his body to. Heartbreakingly, when he read over his own list, he started to weep.
Farrell felt “so sad” that anybody could put themselves through so much to “feel human or have a good time”. Thankfully, he had one saving grace. His family.
27. His Family Saved Him
Down the road, Farrell admitted that he’d been stuck in a vicious cycle where he’d spend most nights completely miserable, and his days working. As his sadness threatened to engulf him, his family came to his rescue: "my family stepped in and said, ‘It’s time. You’re killing yourself’”.
The night of Miami Vice’s wrap party, Farrell finally checked into rehab. The disturbed actor was finally turning his life around—and yet, he was still a magnet for drama.
28. He Had A Deranged Fan
Colin Farrell’s most twisted interaction with a “fan” happened during his appearance on The Tonight Show with Jay Leno.
In the summer of 2006, Farrell sat down across from Leno, completely oblivious to the fact that the interview was about to take a bizarre turn. Her name was Dessarae Bradford—and she had a sinister plan up her sleeve.
29. His Fan Crashed His Interview
During the show, Bradford slipped past security unnoticed and walked on stage. Not only did she confront Farrell, but she completely lost it. She hurled a self-published exposé about the actor onto Leno’s desk.
No doubt bewildered, Farrell guided the deranged woman toward security—and that’s when she screamed, “I’ll see you in court!” But the fiasco was still far from over.
30. He Obtained A Restraining Order
Fans are wonderful...until one of them takes their obsession to a whole new level. Farrell truly had his hands full with Dessarae Bradford. After authorities released her from custody, the actor wasn’t taking any chances. The very next day, he had a restraining order against her. But did Bradford throw in the towel? Absolutely not.
31. His Infamous Interview Got Edited
Audiences never got to see Colin Farrell’s unhinged fan in action. The footage of her on The Tonight Show with Jay Leno never saw the light of day. But despite the restraining order, Bradford continued to insert herself into Farrell’s life.
She tried to sue him twice more, failing due to an obvious lack of evidence.
32. He Started Over
Colin Farrell had been through the wringer by the time director Martin McDonagh approached him with a role in his next project In Bruges. Farrell thought it was an outstanding script, but his response to the director was rather unexpected.
In fact, Farrell later confessed that he tried to convince McDonagh to not cast him.
33. He Didn't Want To Be A Burden
Farrell told McDonagh, “You really shouldn’t hire me. You should hire someone else”. He elaborated, saying that he was wary that his reputation for debauchery might take away from the film’s success. He knew that his name carried a certain amount of “baggage”.
But McDonagh didn’t care. He wanted Farrell no matter what.
34. He Nailed A Difficult Role
In the dark comedy In Bruges, Farrell plays Ray, a character who drinks copiously, uses substances, and even contemplates taking his own life. For a recently recovered addict, this part hit brutally close to home. However, it also set him on a new path.
The film was a huge success, and Farrell even snagged a Golden Globe for his performance. However, despite his new lease on life, Farrell still had a plethora of personal struggles.
35. His Son Has A Rare Disorder
By the time Farrell starred in In Bruges, he’d already had his first son James with model Kim Bordenave. James had been born back in 2003, but it wasn’t until 2007 that the actor revealed a very personal detail about his son.
Farrell divulged that James had a rare genetic disorder called Angelman syndrome, which is characterized by an excitable demeanor, problems with speech, as well as an intellectual delay.
And then there was the actor’s dramatic love life.
36. He Dated A Student
Colin Farrell was a known Irish lothario, but after finally taking the reins on his addiction, he may have been looking for something a little more stable. In fact, he decided to date someone completely outside of his industry.
Her name was Muireann McDonnell, a Trinity College medical student. But if Farrell thought he’d be leaving a life of Hollywood drama behind him, he was so wrong.
37. His Girlfriend Had Baggage
Farrell knew that he came with baggage, but he might not have known that his new “normal” girlfriend also came with a past.
You see, McDonnell had a very devoted ex-boyfriend named John Marc Knight. And sadly, Knight had trouble coping with his failed relationship with McDonnell. The consequences were utterly heartbreaking.
38. He Landed In A Twisted Love Triangle
Farrell found himself in the middle of a twisted love triangle when McDonnell received three chilling text messages from her ex. One read that he loved her “too much,” apologizing for what he planned to do. Concerned about the disturbing texts, McDonnell alerted Knight’s mother. But it was already too late.
39. He Was A Rebound
Sadly, McDonnell’s ex-boyfriend had hung himself from a neighbor’s tree, and his mother found him the following day. Knight had been noticeably low-spirited after the breakup, while McDonnell had clearly moved on with Farrell—the Hollywood bad boy.
In the end, Farrell’s decision to date a student did not lead to a “happily ever after”—but, as we’ll see, neither did most of his romantic pursuits.
40. He Fancied An Older Woman
When Colin Farrell was 28, he shared some drinks with his co-star, 69-year-old Dame Eileen Atkins. As the story goes, when she got up to return to her hotel room, Farrell told her, “I’ll see you 10 minutes”. She thought he was just joking, but boy was she wrong.
After getting ready for bed and taking off all her makeup, Atkins heard a knock at her door.
41. He Tried To Seduce Her
Wearing her nightgown and slightly apprehensive, Atkins opened the door—and there he was. Colin Farrell. Primed for a night of seduction. Well, unfortunately for Farrell, Eileen Atkins turned him down…but he persisted.
In a later interview, she explained the night in detail: “I said, ‘Look, I want to read my book,’ and he said, ‘I’ll read it to you’”.
42. He Was Enchanting
Finally, Atkins let Farrell into her hotel room, allowing him to read to her for a while as long he promised to leave. Soon, the reading turned into an engaging conversation, which led to something more. Atkins remembers Farrell pulling back the covers and trying to get into bed with her.
Still, she refused to give in. But despite the awkwardness of the situation, his proposition didn’t leave a sour taste in her mouth, and she later described him as “enchanting”. Of course, Atkins wasn’t the only older woman Farrell had romantic feelings for.
43. He Crossed Paths With An Icon
Perhaps one of the most unusual chapters of Colin Farrell’s life was his intensely close relationship with the Hollywood icon Elizabeth Taylor.
In 2009, both actors found themselves at Cedars-Sinai Medical Center. Farrell eagerly awaited the birth of his son while Taylor had just undergone a heart procedure. This coincidence had a shocking ripple effect.
44. He Sent Her Flowers
Farrell learned of Taylor’s condition during his stay and afterward, wanted to send her some flowers. But when he contacted his publicist about said gesture, he was in for a touching surprise.
His publicist informed him of yet another funny coincidence. Taylor had already sent flowers to Farrell—an orchid to celebrate his new baby. The actor was touched, but their story didn’t end there.
45. He Wanted To Meet Her
The orchid Taylor had sent Farrell also came with a personalized, handwritten note. This heartfelt exchange made Farrell want to see Taylor in person, and he asked his publicist to set something up. It was a meeting that sparked something special—and the deep connection that grew between the two actors had a profound effect on Farrell.
46. He Had Romantic Feelings For Her
In a later interview, Farrell opened up about how he truly felt about Taylor: “It was kind of like the last—it feels like in my head, not her, I'm projecting, but the last kind of romantic relationship I had. Which was never consummated”.
It was an unlikely friendship, but the two actors had many things in common.
47. He Couldn't Sleep
Colin Farrell has struggled with insomnia since he was young, and he soon discovered that Elizabeth Taylor was also a night owl. They’d phone one another as late as 2 am in the morning, chatting up a storm late into the night.
In Taylor's authorized biography, Kate Andersen Brower wrote about how Farrell reminded the actress of Richard Burton—"the great love of her life". But their relationship wasn’t always smooth sailing.
48. He Ghosted Her
While going through a rough patch, Farrell confessed that he’d ghosted Taylor for many weeks. But when he finally called her up, he made an unnerving discovery: She was very upset with him.
He shared, “She went, ‘Why didn’t you call?’ And I said, ‘Because, stuff is going on. My head was wrecked. I was in a bad mood’". Her response was so scathing—it's unforgettable.
49. He Wanted To Be Her Eighth Husband
Elizabeth Taylor dished out a dose of tough love. According to Farrell, she said, “Well, that’s not the kind of friendship I’m interested in, if you’re only ever going to bring me your sunny days”.
Sadly, their friendship only lasted a few years, as Taylor passed in 2011. The actress had been married seven times, and it was Farrell who admitted, “I wanted to be number eight but we ran out of road”.
50. He Kissed A Pop Star
Colin Farrell certainly has dated a wide range of women, but he really made a splash at the start of 2003, when he showed up to his film premiere with Britney Spears.
Later that night, the two stars were spotted making out at the Chateau Marmont, but later, Farrell claimed they were just “mates”. Sounds like a typical fling right? Wrong.
51. He Sent Her A Deranged "Gift"
After their brief relationship soured, Farrell decided to send Britney some gag gifts—but they reportedly infuriated her.
Farrell’s “gift” was a shirt that read, “I slept with Colin Farrell and all I got was this lousy T-shirt”. But he didn’t stop there. He also sent her a bumper sticker that reflected a similar sentiment: "Honk if you've slept with Colin Farrell”.