In the dazzling world of Hollywood, George Clooney isn’t just an Oscar-winning actor and humanitarian; he’s also a legendary prankster, known for orchestrating elaborate jokes that become unforgettable tales shared across the entertainment industry.
While the word ‘prank’ often conjures images of innocent, fleeting jokes, Clooney’s approach elevates it to an art form, characterized by meticulous planning, audacious execution, and a knack for tapping into the vulnerabilities of even the most seasoned celebrities. These aren’t just simple gags; they are intricate narratives designed to disarm, surprise, and ultimately, bring laughter, even if the journey there involves a moment of genuine confusion or a brush with unexpected trouble.
Join us as we explore George Clooney’s most iconic pranks, the ‘harmless’ hijinks that pushed friendships to the limit, sparked declarations of ‘war,’ and cemented his status as Hollywood’s ultimate practical joker, revealing a side of him as captivating as his acting.
1. **The Brad Pitt ‘Lestat’ Letters: A Masterclass in Deception**
Among George Clooney’s most “brutal” and intricately designed pranks was his elaborate scheme involving fake stationery seemingly from his long-time friend and co-star, Brad Pitt. This wasn’t merely a handwritten note; it was a carefully orchestrated campaign of deception, targeting multiple A-listers and leveraging inside jokes from Hollywood history. Clooney revealed on ‘Jimmy Kimmel Live!’ that he had obtained false stationery designed to appear to be from Pitt, enabling him to craft a series of letters that would surely cause a stir within their elite circle.
Armed with meticulously crafted counterfeit letterheads, Clooney set out to convince prominent Hollywood figures, including Tom Cruise and Meryl Streep, that Brad Pitt was engaging in unusual behavior, weaving believable narratives based on their professional relationships.
One particularly memorable letter was dispatched to Tom Cruise, suggesting a sequel to their 1994 hit “Interview with the Vampire 2.” The kicker? The letter, allegedly from Pitt, stated that “this time Brad wants to play Lestat,” a role famously portrayed by Cruise in the original film. The irony and potential for awkwardness were brilliantly high. Another letter, equally cunning, went to Meryl Streep, accompanied by a box of CDs for dialect coaching. In this note, Clooney, still posing as Pitt, claimed, “This guy helped me with my accent in Troy and I think it could really help you.” This jab at Streep, renowned for her unparalleled skill with accents and multiple Oscar wins, showcased Clooney’s sharp wit and willingness to poke fun at even the most celebrated talents.
The prank, as expected, yielded priceless reactions. Jimmy Kimmel himself had heard of this particular escapade, sharing Brad Pitt’s reaction after he discovered he had been punked. Kimmel recounted, “Brad this afternoon said that Tom called him and said, ‘Yeah, it’s cool, you can play Lestat, that’s fine, I’m OK with that,'” to which Pitt was understandably confused, asking, “‘What are you talking about?'” While these pranks usually make for a good laugh, Clooney admits that the subjects of the pranks eventually catch on, often by connecting the dots or simply knowing his mischievous reputation. “There’s usually some guess involved with me,” Clooney acknowledged, “Usually somehow they figure it out.” The enduring nature of his friendships, despite such elaborate trickery, speaks volumes about the bonds he shares with his Hollywood peers.
2. **The Oscar and SAG Award in Richard Kind’s Suitcase: A Heavy-Handed Joke**
Richard Kind, a respected character actor and a long-time friend of George Clooney, has been the target of numerous pranks throughout their decades-long friendship. Their bond, forged in their early days as struggling roommates in Los Angeles, has provided fertile ground for Clooney’s mischievous creativity. One unforgettable incident, recounted by Kind himself on the ‘Still Here Hollywood’ podcast with Steve Kmetko, perfectly illustrates Clooney’s knack for turning a simple gesture into an elaborate, inconvenient, and ultimately hilarious practical joke.
The stage for this particular prank was set years ago, before Clooney’s marriage to Amal and the birth of their children, a time when Kind frequently stayed at Clooney’s Los Angeles home. Kind was preparing for a trip to Las Vegas for a publicity event, with his suitcase ready at the base of the stairs as he waited for his car to the airport. Clooney, ever the unassuming conspirator, sat with him, engaging in casual conversation, giving no hint of the surprise he was about to unleash.
Kind remembered a brief moment when he stepped away to retrieve a forgotten item upstairs, leaving his luggage unattended. This small window of opportunity was all Clooney needed. As Kind returned downstairs and the car arrived, the driver loaded his bag into the trunk, completely unaware of its illicit cargo. It wasn’t until Kind went through the TSA line at Burbank Airport that the prank truly came to light. He was pulled aside, and upon inspection of his luggage, agents discovered two unexpected, very heavy items: an Oscar and a SAG Award.
Clooney, who has earned an Oscar either as Best Supporting Actor for ‘Syriana’ or as producer for ‘Argo,’ and four SAG Awards for his work on ‘ER,’ had strategically packed his own prestigious accolades into his friend’s suitcase. Kind vividly recalled the burden, stating, “the SAG award is very heavy. It’s about 12 pounds. An Oscar, I don’t know, but I [have to] schlep them to Vegas for the weekend.” The image of Kind, a respected actor, being forced to transport another celebrity’s heavy, prized awards through airport security and then for an entire weekend, all thanks to his friend’s “harmless” joke, has become a legendary anecdote in Hollywood, underscoring the playful yet demanding nature of Clooney’s pranking style.
3. **The ‘F**k Cops’ Bumper Sticker on Brad Pitt’s Car: A Brush with the Law**
While many of George Clooney’s pranks aim for pure comedic effect or mild inconvenience, one particular incident involving Brad Pitt ventured into a territory that could have, quite genuinely, led to serious trouble for his Hollywood bestie. This prank wasn’t about clever letters or heavy awards; it was a daring move that placed Pitt directly in the line of potential legal scrutiny, showcasing Clooney’s willingness to push boundaries even further.
According to Pop Sugar, back in 2001, Clooney was dangerously close to being taken off Brad Pitt’s BFF list for good. His weapon of choice? A seemingly innocuous bumper sticker, but one with a highly provocative message. Without Pitt’s knowledge or consent, Clooney covertly placed a sticker on the back of Pitt’s car that boldly declared, “F**k Cops.” This act, stealthily executed, set the stage for an inevitable and almost immediate confrontation.
It didn’t take long for the consequences of Clooney’s audacious prank to manifest. Pitt, unknowingly driving around with the inflammatory message prominently displayed on his vehicle, was pulled over by the police. The scenario, undoubtedly tense for Pitt, highlights the fine line between humor and potential legal ramifications that Clooney sometimes treads with his pranks. While the specific outcome of the police stop isn’t detailed, the context implies a significant level of discomfort and explanation for Pitt.
The aftermath saw Pitt ‘declare war’ on his best friend, a clear sign of significant annoyance and a temporary rift, though their friendship ultimately prevailed, highlighting how even a ‘harmless’ prank can lead to unexpected consequences, like an A-lister being pulled over by authorities.
4. **The Fake Brangelina Wedding in Lake Como: Tricking the Media**
During a period of intense media scrutiny surrounding Hollywood’s most talked-about couple, Brad Pitt and Angelina Jolie – affectionately dubbed ‘Brangelina’ – George Clooney once again demonstrated his mischievous genius by orchestrating a prank that tricked not just his friends, but an entire contingent of international media. This elaborate scheme unfolded in the early days of Pitt and Jolie’s relationship, shortly after Pitt’s highly publicized separation from Jennifer Aniston, making their every move a subject of global fascination.
Observing the intense public fascination with Pitt and Jolie’s potential wedding, and a circulating rumor about a ceremony at his Lake Como estate, Clooney saw a perfect opportunity to orchestrate a grand prank that would captivate the media.
Clooney recounts proposing to Pitt, “So I called Brad up and I said we should sort of let it leak out and then hire a bunch of kids dressed up to pretend to be getting married on that day and let everybody rent helicopters and spend a fortune,” turning a rumor into a massive, media-fooling production.
The extent to which the ‘kids dressed up’ element was fully executed remains a subject of Hollywood legend, but the intent and the impact of the fake wedding leak were undeniable. Clooney successfully managed to trick the local media, creating a frenzy around his Lake Como villa, all for the sake of a joke. While Pitt and Jolie did eventually marry in 2014, it was at their estate in the South of France, not Lake Como, and Clooney himself married human rights lawyer Amal Alamuddin in 2014, with Brad and Angie notably missing the festivities due to filming ‘By the Sea.’ This elaborate ruse cemented Clooney’s reputation not just as a prankster of friends, but as a cunning strategist capable of manipulating entire media landscapes for a laugh.
5. **Rolling Richard Kind into the Casino: A Public Spectacle**
The camaraderie between George Clooney and Richard Kind has long been a source of legendary Hollywood tales, often centered around Clooney’s inventive pranks, which demonstrate both his mischievous spirit and the depth of their enduring friendship. One such incident, an unforgettable and highly public spectacle, unfolded during the star-studded filming of “Ocean’s Eleven,” a blockbuster project that brought together an ensemble cast including luminaries like Julia Roberts and Matt Damon. Everyone was staying at the opulent Bellagio Hotel in Las Vegas, a setting synonymous with luxury and high-stakes glamour, yet Clooney saw it as a prime opportunity to inject a dose of his signature mischief into a quiet, unsuspecting moment.
Kind, visiting Clooney on set, found himself at the receiving end of this particular escapade, though he was entirely oblivious to the unfolding plot. After a lively evening of socializing with the cast and crew, the respected character actor succumbed to sleep, finding slumber on a rollaway cot. This seemingly innocent situation, however, presented Clooney with a perfect, if somewhat audacious, canvas for one of his most public practical jokes, transforming a private snooze into an unexpected, bizarre, and utterly hilarious casino attraction.
With a seasoned prankster’s stealth and comedic timing, Clooney and his inner circle discreetly moved the unsuspecting, sleeping Kind onto a cot right into the lively center of the Bellagio casino floor, creating a surreal spectacle for all to witness.
The reaction of the casino patrons, encountering a sleeping Richard Kind in such an improbable setting, must have been priceless. The sheer audacity of rolling a sleeping A-lister into a highly public space like a casino underscored Clooney’s unparalleled willingness to push the boundaries of humor, transforming a simple act of slumber into a moment of collective bewilderment and laughter. The prank created a truly unforgettable anecdote, adding another memorable chapter to the enduring saga of George Clooney’s mischievous genius and his playful, yet demanding, relationship with one of his dearest friends, proving that even in the most glamorous settings, a touch of well-placed chaos can always be found.
6. **The Case of the Mysterious Missing Litter: A Long-Running Cat Caper**
Among the annals of George Clooney’s most brilliantly executed and psychologically intricate pranks, the tale of Richard Kind’s cat litter box stands out as a true masterclass in patience and subtle deception. This particular escapade, now a legendary story in their shared history, dates back to their early days as struggling roommates in Los Angeles, a formative period that laid the groundwork for their decades-long friendship and countless shared anecdotes that reveal the depth and unique dynamic of their bond. It’s a story that perfectly highlights Clooney’s extraordinary commitment to a joke, no matter how long it takes to unfold.
For weeks on end, Kind found himself increasingly perplexed and genuinely worried about the health and well-being of his beloved feline companion. The reason for his growing anxiety was peculiar: despite regular use by the cat, its litter box consistently appeared clean, with no solid waste to be found. This baffling anomaly began to weigh heavily on Kind, who started to suspect a serious, inexplicable illness in his cherished pet, creating a quiet yet intense personal drama within their shared living space.
Unbeknownst to Kind, the orchestrator of this growing mystery was none other than his seemingly concerned roommate, George Clooney. With meticulous care and an almost surgical precision, Clooney was covertly and diligently cleaning the litter box behind Kind’s back, day after day. This calculated deception was the lynchpin of the prank, creating an environment of genuine confusion and distress for Kind, who was completely unaware that his trusted friend was the architect of his cat-related worries.
As Kind’s worry mounted, he naturally consulted Clooney, seeking answers for his cat’s unusual and alarming habits. Clooney, however, maintained an expertly crafted poker face, denying any involvement and even subtly amplifying Kind’s anxiety about the animal’s well-being. This calculated manipulation added profound psychological layers to the prank, making Kind genuinely believe his cat was suffering from some mysterious, undiagnosable illness, all while Clooney silently orchestrated the unfolding, agonizing drama, enjoying every moment of his friend’s bewilderment.
The much-anticipated punchline finally arrived when Clooney, having drawn out the suspense for weeks, decided it was time to bring the elaborate ruse to an end. After meticulously cleaning the litter box for an extended period, he himself strategically contributed to its contents, creating the unmistakable tell-tale sign of a healthy, functioning cat that Kind had been so desperately, and anxiously, looking for. The sudden, albeit delayed, appearance of waste after weeks of perplexing absence finally clued Kind in on the secret prank, revealing the long-running deception. It was a slow burn, meticulously planned and executed with unparalleled dedication, demonstrating Clooney’s commitment to a long-form gag that tested the limits of his friend’s patience, his own capacity for sustained deception, and cemented its place as one of his most legendary acts of mischief.
7.George Clooney’s prank repertoire goes beyond physical gags, extending to masterful written stunts, like impersonating former President Bill Clinton to send critical ‘movie’ reviews, as he humorously revealed on ‘Jimmy Kimmel Live!’, showcasing a more subtly cutting side of his creativity.
The brilliant concept behind these particular letters was both disarmingly simple and yet exquisitely designed to tap into a unique vulnerability shared by Hollywood’s elite: their filmography, and specifically, the less-than-stellar entries within it. Clooney would meticulously craft notes, seemingly penned by Bill Clinton, and dispatch them to various friends and peers across the industry. The core content of these letters was a subtly pointed, often humorous, critique. The former President, so the letters claimed, had apparently watched their “worst” movie during a flight, perhaps a long, transatlantic journey, and felt compelled to share his thoughts. Imagine the blend of bewilderment, amusement, and perhaps a touch of genuine discomfort upon receiving such a highly specific and gently critical review from a former head of state; the humor, and the potential for awkwardness, would be undeniable and deeply personal.
This nuanced prank stood in stark contrast to his earlier ‘Lestat’ letters to Tom Cruise and Meryl Streep, which focused on professional jabs and playful criticisms of acting accents. The ‘Bill Clinton’ letters, instead, expertly played on the universal actor’s fear of a negative critical reception, albeit delivered with a presidential stamp of approval. This fear is amplified exponentially by the sheer prestige and unexpected nature of the supposed sender. It highlighted Clooney’s profound understanding of the unique anxieties his celebrity friends face, turning their professional insecurities into a private source of clever amusement for himself and his inner circle.
Clooney’s audacity in impersonating a former President for a joke underscores his dramatic flair and playful nerve, with friends now understandably ‘terrified’ of him, even joking he “could put a dead body in my apartment,” a testament to his mastery of unsettlingly hilarious hijinks.
8. **The Two-Year Prank in the Making: Brad Pitt’s Career-Ending Suspense**
If there’s one definitive lesson George Clooney’s long and illustrious history of pranks teaches us, it’s that his mischievous mind is not bound by fleeting impulses; it is always actively at work, often orchestrating elaborate schemes that are meticulously planned and unfold over significant, sometimes even years-long, periods. The ultimate testament to this extraordinary dedication to mischief comes in the form of a particularly ominous, long-running prank he publicly revealed to be preparing for his dear friend, frequent collaborator, and fellow A-lister, Brad Pitt. This isn’t just a fleeting joke or a spontaneous gag; it’s a strategic, carefully constructed operation, already years in the making, designed for maximum, and potentially devastating, impact.
During a revealing appearance on “Inside the Actor’s Studio” back in 2012, Clooney offered a tantalizing, almost chilling, glimpse into his ongoing masterpiece of mischief. With a gleam in his eye, he declared to the audience and host, “I’m working on [a prank] right now for Brad Pitt. It might end his career. I’ve been working on it for two years. I’m not going to tell you what it is, but just know, I got it.” This chillingly confident statement alone sent ripples of both amusement and genuine apprehension throughout Hollywood and amongst their legion of fans, creating a palpable sense of suspense around what grand, potentially career-altering, scheme Clooney had meticulously cooked up for his close confidant.
The very idea of a prank being meticulously planned for two years, with the audacious, albeit playful, stated goal of potentially “ending a career,” speaks profound volumes about the depth of Clooney’s commitment to his craft as a prankster. It unequivocally moves beyond simple, spur-of-the-moment gags into a realm of intricate, long-term psychological warfare, albeit one rooted in a deep friendship. Pitt, having already been subjected to the public embarrassment of the ‘F**k Cops’ bumper sticker incident and the playful deception of the ‘Lestat’ letters, would undoubtedly have very good reason to “be worried,” as the context suggests. This is not merely a threat; it’s a promise from Hollywood’s most notorious prankster.
This unseen, unexecuted, but very real ‘prank in the making’ for Brad Pitt is arguably one of Clooney’s most iconic hijinks, precisely because of its enduring suspense and the sheer scale of its anticipation. It reveals the true extent of his mischievous creativity, demonstrating a mind that constantly seeks new ways to surprise and delight (or perhaps, delightfully torment) his friends. The mystery of what precisely Clooney “got” for Pitt continues to loom large, a powerful testament to his lasting legacy and the indelible way he keeps everyone, especially his closest friends, perpetually on their toes, never truly knowing when, or how, the next elaborate and unforgettable surprise might finally strike. This level of dedication to a joke solidifies his reputation as the ultimate master of elaborate hijinks.
From impersonating presidents and orchestrating media circuses to elaborate multi-year schemes, George Clooney has rightfully earned his title as Hollywood’s prank king, creating meticulously planned narratives that reveal a playful, audacious spirit and celebrate the bonds of friendship.
