There are two stories currently circulating about George Clooney’s generosity. One is about his babies. The other is about his friends. We’ll come back to babies. 

The story about George Clooney’s friends goes like this: in 2013, George invited 14 of his closest buddies over for dinner. The point of the dinner was to gift them each 1 million dollars which was delivered in suitcases packed with 20 dollar bills. According to E! News, George’s best friend Rande Gerber (dad to Kaia, husband of Cindy) told this story on an MSNBC show called Headliners. Rande recalled George giving a speech before each of the men opened their money cases: 
'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 couch. I'm so fortunate in my life to have all of you and I couldn't be where I am today without all of 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.'"

There is so much to unpack here I don’t know where to start. Let’s start with the dramatic AF way George decided to unveil this gift to his friends. He made 14 people open suitcases stacked with bills at the same time. He could have written cheques. He could have told them individually.  Instead, he did it in the most extra way possible. I’m not judging him. I can’t say I wouldn’t have done it in the same way. I would have announced it in my best Oprah voice, “You’re getting a million dollars! You’re getting a million dollars!” while throwing bills in the sky. This is why I can’t have nice things. 
At the time, Rande says George called this group “The Boys” and that they consisted of guys who really needed the money. George paid their taxes AND gave them a million dollars. Sure, it’s sweet and really f-cking generous but I can’t help but picturing another A-List bachelor (this was pre-Amal) who has a nickname for his friend group doing something similar. Do you think Leo has gifted The Wolf Pack a sh-t ton of money? Do you think he did it with Deal or No Deal briefcases too? In Leo’s case, does the money come with conditions? In George’s case, it doesn’t sound like it did but how do you get around that? I have many questions about the logistics of celebrities giving their friends exorbitant amounts of money but here’s my biggest one: what happens next? How do you give them any gifts after that? Like a Roomba doesn’t quite cut it after you’ve opened a briefcase full of cash, right? And if you’re the friend, how do you move on and not feel like you’re constantly indebted to your homeboy? I would be suuuper awkward about this whole thing. I can’t even tip my hairdresser without stuttering, getting all weird and literally shoving money in her face to get it over with. And we’ve been together for years. This is why people say to never win the lottery. It would f-ck up all my relationships. How are George, Rande and “The Boys” still cool? Rande says he told this story to shed light on George Clooney’s character. He’s George, The Generous. 

Now that George is a dad, his generosity is manifesting in different ways. Page Six reports that George and Amal were on a flight with their 6 month-old twins recently and they preemptively handed out noise cancelling headphones to every other passenger. The headphones came with a note, “apologizing ahead of time” for the twins’ crying. The headphones had his tequila brand logo on them. I’m going to resist the urge to say that this was just an elaborate marketing scheme. My brother and sister-in-law just flew from Toronto to Vancouver with a newborn. They were STRESSED that my nephew would cry the whole flight and disrupt the other passengers. This is a legitimate, normal new parent fear. This may be the most normal thing George and Amal have ever done. Most new parents can’t afford free headphones for a whole flight but I’ve heard stories of parents passing out cookies with notes attached apologizing for their kids. It’s usually the woman’s idea. My guess is that this was all Amal. I don’t think George gets extra generosity points here. Plus, if I was on that flight after reading the friends story, I’d be like f-ck headphones, George, where’s my money? 
Both stories make George Clooney look really good – like a selfless friend and a doting father. I’ve been trying to figure out what George is promoting. These stories are both too good for publicity for George not to be promoting something. I can only find this clip from Jimmy Kimmel Live this week of Jimmy and George playing a game while sipping on some strategically placed Casamigos Tequila. Does Generous George put you in the mood for some Margaritas?