As one of the ‘90s biggest screen heartthrobs, George Clooney has enjoyed his fair share of partying and boozing throughout the years. So much so that George credits one of the greatest bits of advice he ever received to his aunt.

who told him at the age of 7 “Don’t miss the grape and the grain.. grain and grape no wine in like tequila or vodka and you know champagne ”.  Great advice if you want to avoid hangovers, over consumption.  But in his later years, Clooney also turned his love of booze into a business venture. Decades after he became an A-list actor, George co-founded the Casamigos tequila brand in 2013, a move which has made him a billionaire.

But how did the two time sexiest man alive become a spirits mogul and what are some of his most fun drinking stories.

Early Life and Acting

George was born in 1961 in Lexington, Kentucky and due to his father’s career of journalist, anchorman and TV host spent most of his childhood moving around Ohio and Kentucky.  Although as a kid he occasionally appeared on his father’s variety show – on one occasion as a cigar smoking leprechaun, he had very little intention of following acting. He attended several schools including Augusta High School and later both Northern Kentucky University and the University of Cincinnati, but dropped out of both to pursue a career in acting.  Before he broke into acting, George worked various odd jobs – selling women’s shoes, cutting tobacco and construction worker. 

Clooney got his first taste of the film industry when he worked as a production assistant on one of his cousin Miguel Ferrer’s movies.  This encouraged him to move to Los Angeles in 1982, where he’d audition for small roles.  Throughout the ‘80s, he’d appear in low-profile TV series and movies and have recurring roles in “The Facts of Life” and “Roseanne”, which gave him some recognition before he got his big break out as Dr. Doug Ross in medical drama “ER”.  While still on the show, Clooney began taking the film roles which made him a household name, starring in “Dusk Till Dawn” in 1996, allowing him to show a different side of his persona than just handsome doctor.

By the 2000s, films like “Three Kings”, the Coen Brother’s “O Brother, Where Art Thou?” and of course, the Ocean’s Eleven series which cemented his name as an A-lister.  It’s this status which helped build the marketing of the tequila brand Casamigos that he’d venture into.

The official story of Casamigos is a bit of a fairy tale.   Apparently both he and his buddies, Rande Geber and Mike Meldman were building vacation homes in Mexico where they often drank together.  After trying a plethora of different brands from local bars and restaurants they thought “what if we made our own tequila?”. George himself wanted one which wasn’t too bitter, too sweet and too hangover-inducing, and so had a distiller make it for them.  This was then delivered to a property known as Casamigos or “House of Friends”.  Supposedly this was just for personal consumption, but their distiller insisted on a license after making 1,000 bottles.  Thus, the brand was launched in 2013 and was made available to the public.

However, as we all know, sometimes the real story isn’t necessarily as marketable.  A society raised on the dream of making it big in Hollywood tends to prefer the idea of accidental success, rather than deliberate.  Long before their distiller had suggested acquiring a license, Clooney and his buddies had already filed for a few trademarks.

This extends beyond just Casamigos but also a few taglines, including “It could happen.  Please drink responsibly.” and “Brought to you by those who drink it”.  

Additionally whilst Clooney’s status and Rande Gerber’s business acumen might have done some heavy lifting brand, it’s perhaps the work of the  third partner, Mike Meldman which made the tequila a billion dollar brand.  Meldman owns real estate development company called the “Discover Land Company” – which turned out to be the secret to alcohol sales is in store or retail distribution.  Mike put Casamigos into one of his 30 locations, then as Rande and George were the face of the company, Mike was using his 100s of distribution connections to put the brand in 30 of the most pristine places in the world and push their tequila.  Sometimes it’s not the face that makes the millions, it’s the guy that opens the door 

Since then, Diageo, the biggest guns in the alcohol business acquired the tequila brand for $1 Billion. The partners got $700 million upfront, and the remaining $300 million will be paid to them based on the performance of the brand over the next 10 years. 

Drinking Stories

In almost rockstar fashion, Clooney has always been a fan of drinking and partying.  In one interview, he admitted “I drink at times too much. I do enjoy drinking, and there have been times in my life when it’s crossed the line from being fun to having to drink late at night for absolutely no reason. So what I do is, I stop.”  Though he may go through periods of abstinence to clear both his liver and mind up, there are still plenty of fun anecdotes about the annoyingly handsome hunk.

Drinking with Brad Pitt

Having worked on a few films like “Burn After Reading” and “Wolfs”, George and Brad have been long time buddies.  Sometimes it has got out of hand.  The late great Jerry Weintraub recounted a tale where he engaged in a drinking contest on a long haul with Pitt and Clooney.  Over confident in his ability, due to being “taught by Sinatra”, and being “known to drink a few vodkas.. well maybe more than a few” took the two on and didn’t came out on top.  

By the end of it, Weintraub “seeing two Brad Pitts and two George Clooneys” and found himself pass out.  When he woke up in Vegas, he realized he’d been the victim of a cruel prank –  “They put M&Ms all through my body – in my underwear, socks, shoes and they all melted!”  

Talk about a sticky situation.

Since then, Brad has advocated for a booze-free lifestyle and in 2017 reportedly told his friend George to “sober up”.

George doesn’t seem to have taken the message to heart.

Drinking Over COVID Quarantine

If you thought you were the only one to enjoy a tipple over the pandemic, think again.  Pouring “lockdown measures” wasn’t reserved for the commoner, but in George’s case enjoyed by the rich and famous too.  When asked in 2020 by Good Morning America how he got through the pandemic, he replied “Well, you know, I drink, mostly, George. I drink,” joked the Casamigos co-founder, laughing. “That’s how you get through it.”  Well, it might have helped with the other lockdown hobbies he acquired – doing “two or three loads of laundry a day, dishes all fucking  

day, because these kids are slobs, apparently you have to wash them once in a while”

His hardest experience over lockdown was being separated with his mother, father and sister in Kentucky.  Perhaps because enjoyment of libations is tendency which seems to run in the family.

Drunk On Set

In a conversation for Variety’s Actors on Actors, George Clooney and Michelle Pfeiffer reminisced about their time filming the 1996 romantic comedy One Fine Day. Clooney shared that the film, which is now considered a beloved classic, initially bombed at the box office. Pfeiffer explained that the studio had prematurely moved up the release date, which hurt its success. Clooney noted that despite its failure at the time, his wife and her friends love the movie today.

They also recalled their experiences on set. Pfeiffer remembered being busy with her young children and not socializing much with Clooney, which made her think he might have found her unfriendly. Clooney humorously recounted a day he arrived on set still drunk after a night of drinking, surprising Pfeiffer with his condition. He tried to mask his breath with mouth spray during their scenes together.

One Night With Cindy

In one of the earlier days of Casamigos, Rande Gerber and George spent a night drinking.  One night, after consuming an entire bottle of their tequila, Clooney ended up in the guest bedroom at Gerber’s house. In a funny mix-up, Gerber’s wife, Cindy Crawford, accidentally climbed into bed with Clooney, thinking it was her husband.