The Time George Clooney Gave Me A Million Dollars

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I’d like to begin this story by swearing by its authenticity. This isn’t based on a true story, and it’s not a version of somebody else’s tale. This happened.

It was another casual Friday night dinner at George’s house back in 2013. He had just met Amal and they weren’t publically dating yet so this was George in his element with his closest friends. No wife, no twins. He smiled as we entered the main dining room, of which there were four. In front of each place setting there was a black designer luggage bag. It would be a night unlike anything in recent memory…

Earlier that week, Rande Gerber, one of me and George’s best friends who happens to be married to Cindy Crawford, told me that George had asked him to spread the word to ‘The Boys’ (that’s what George called his closest group of 14 guy friends) that this would be a very special dinner. Those of us who had grown up with George in Lexington knew that this could very well be one of his elaborate pranks. Needless to say, we braced ourselves as we walked into Villa Oleandra that evening.

I’d been there dozens of times before, but tonight felt different. His trademark smirk that had gotten him so far in life was replaced with a furrowed brow and a serious look across his dancing brown eyes. He cleared his throat as we, his 14 closest friends, took our seats. George began to speak, “Listen, I want you guys to know how much you’ve meant to me and how much you mean to me in my life. I came to L.A., I slept on your couches. I’m so fortunate in my life to have all of you and I couldn’t be where I am today without you. So, it was really important to me that while we’re still all here together, that I give back. So I want you all to open your suitcases.”

We open up the bags, and I shit you not, inside each was $1 million in $20 bills. Every single one of us got $1 million. My heart stopped. Me: little known comedian, writer and podcast host JR Hickey has benefited immensely from my friendship with George Clooney. I’ve stayed on his houseboat rent free for months at a time, I was able to bring the Capital F Fiancee to the London premiere of Hail, Caesar! but George had never straight up given me cash before.

He continued, “I know we’ve all been through some hard times, and some of you are still going through it. You don’t have to worry about your kids, you don’t have to worry about, you know, school, you don’t have to worry about paying your mortgage.” The stunned silence was deafening. Matt Damon mouths to me, “What do I need another million dollars for?” I mouthed back, “You could actually buy that zoo” and we both smile. Remember, this was 2013.

George glances over at Matt and I and takes a deep breath… “Not only that, I have paid everyone’s taxes so this million dollars is all yours.” What in the holy hell is going on? I thought. Does George have cancer or something? It was here that even Gerber spoke up to object. You see, he and George had just gone in together on a tequila company and it was doing quite well. “George I am absolutely not taking this million dollars,” he started. Immediately George turns to the rest of us and says, “I’m just going to make one more announcement. If Rande doesn’t take the million dollars, nobody gets it.”

That stumped him. Rande ended up donating his million to charity. He and George eventually sold Casamigos Tequila for a billion dollars. The happiness I feel for the success of two of my closest friends is only dwarfed by how tired I am of drinking that tequila. I have so many cases of the stuff in my tiny one bedroom apartment in San Francisco.

Anyways, George got married exactly one year later and it was a weekend I’ll never forget. I’m looking forward to having him and Amal at our wedding next year. I just hope he isn’t embarrassed by the inevitable attention this story will draw.

Oh and what’d I do with my $1 million dollars? I invested it in bitcoin..

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This week on Don’t Take It From Us, I’m playing sick and Jenna Crowley just got back from being trapped at the Seattle airport for nine hours. We discuss Christmas shopping tips, masturbating while traveling internationally and give advice on how to ask your girlfriend’s parents for permission to marry her. Don’t miss next week’s episode where we bring back a bunch of our former guests to open their Secret Santa gifts on the airwaves! Make sure you follow our Spotify playlist here and leave us a 5-Star Review on iTunes!

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JR Hickey

Stand up comedian and writer from Chicago who now resides on the West Coast. JR can be seen performing at Cobbs Comedy Club in San Francisco and Zanies Comedy Clubs in Chicago. His work has been published in the Chicago Tribune and recently he was a part of SF Sketchfest 2015. JR's also the host of the PGP dating podcast Don't Take It From Us. He loves you very, very much.

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