How I Convinced Diddy to Do a Basement Theater Comedy Show Tonight

Thirteen months ago, I put a video on YouTube, completely on a whim. It was Christmas Eve, I was shirtless in a bed at my parents’ house, and in it I was sending a message to entertainment impresario Sean “Diddy” Combs.

I told him about how I wanted to believe that the world was a cool enough place that a guy like him and a guy like me could hang out. I asked him if he would be a guest on my talk show at the UCB Theater in New York. I asked my Twitter followers to help me convince him to do the show by putting up tweets directed at him that involved the hashtag #diddygethard.

A few dedicated people got on board. I thought it was pretty funny. I didn’t think anything would come of it. Mostly, I thought it was a cool way to promote my show that got a lot of people participating.

Then, on December 31, 2009, Diddy sent a tweet back to my friend Winston asking what everyone was talking about with all the #diddygethard stuff. Within minutes, I was on the phone with Diddy. He asked me what my show was about, and I rambled about how it was a talk show and how we try to do a lot of out of the box stuff and how my mission statement with the show is to give the audience something each month that they can’t believe they just saw. Mostly, I kept saying “It’s at the theater Amy Poehler co-owns”, because I had a feeling that chances were he had maybe heard of her a little bit more than he had heard of me.

He said he would do my show. I thanked him profusely and said “People are gonna flip out about this. Thank you. I can’t believe you’re down to do it.”

He said, “Ask and ye shall receive.” Then, he hung up the phone.

Since then, my life has changed.

First off, Diddy went back to being as unattainable as ever. Each month, I dutifully let him know when the show was happening. Sometimes he’d get back to me saying he couldn’t make it that month. Oftentimes, he wouldn’t. I never got mad. I’d read his Twitter and it would be like “Hope I make it from Paris in time to host my after-party for the NBA All-Star game,” and I’d be like “Yeah, that’s fair. Diddy has a lot of other cool-ass shit to do besides my dumb talk show at midnight on a Saturday in a basement comedy theater.”

Here are the ways my life has changed since I first talked to him:

1. Someone asks me about Diddy literally every single day: friends, people who I don’t know message me online, family members I haven’t talked to in years. Sometimes people wait for me after shows at UCB just to ask when Diddy’s coming. My answer has always been “I don’t know! As soon as I know I’ll let everyone know.”

2. I got a TV show. It was on Comedy Central and it was called Big Lake and I got to work with a bunch of my heroes. It was intensely hard and at times really overwhelming but I’m insanely glad I got the opportunity. Ten episodes aired over the summer and now I am figuring out what the next thing is, but the fact that this even happened made me feel OK about the ten plus years I’ve spent trying hard to survive doing comedy.

These things cross over in a few ways. The first is that I sent Diddy a DM on Twitter and very truthfully said “I talked to you on New Year’s Eve and have had the best year of my life. I just got cast as the lead on a TV show. I know this is weird, but I want to thank you. I feel like I’ve had good luck ever since we talked.” He wrote back and said “You’re not the only person who has said that about me. Congrats!”

I also kept my eye on the prize and kept finding ways to try and remind Diddy to do my show. I went to the Sean John store on Fifth Ave and bought a bunch of shirts. Anytime I had to promote Big Lake on camera, I wore Sean John if they let me. My hope was that if pictures or videos showed up, Diddy would see them and realize I was giving him a shout out.

I was a guest on Late Night with Jimmy Fallon as part of the Big Lake promotion, and Jimmy and his producers had heard about all the stuff with Diddy. Those guys have always been nice to me, even though they (accurately) think I’m a real fucking weirdo. They did me a huge solid and talked about the Diddy stuff on the air and even put a graphic of the #diddygethard hashtag on the screen.

That night, #diddygethard exploded all over the internet. After both the east coast and west coast airings of the show, thousands of tweets rolled in.

The next day, Diddy called me again. He was like “Yo, you’ve got some dedicated fans, huh?” and I was like “Yeah, they call themselves the GethTards. But I talked about you on Fallon last night and that’s why it blew up.” And he told me to call him back on Tuesday so we could pick a date and I did and left a voice mail and didn’t hear back and things slipped through the cracks again.

That was on 9/11. So the two days I’d talked to Diddy on the phone were New Year’s Eve and 9/11.

He played SNL in December and I called in some favors from friends who work there and they got me in. My friends Shannon O’Neill, Fran Gillepsie, and Joe Mande came with me because they knew I would be a pussy and chicken out if I saw him. I wore one of my Sean John shirts. We were introduced to him before the show and I was shocked that he knew who I was. He said he was just thinking about how he felt bad since he never did my show. He agreed to film a promo video on Shannon’s flip cam after the show. When SNL wrapped up, we walked down to his dressing room and there were like 30 people there. I tried to run away, but my friends did their job and told me to stop being a pussy. When Diddy walked by, Shannon grabbed his sleeve and he was a man of his word — he filmed a video saying he would do the show and that people should keep reminding him about it via Twitter. After that video was posted, #diddygethard was a trending topic in New York and a whole bunch of newcomers got on board.

People made fun of me throughout the year, but I never gave up. To me, #diddygethard has gone from being a bit to being a phrase that means “never give up” and “be stubborn in the face of doubters” and “do what you do even if other people make fun of you for it.” I know that’s cheesy, but it’s true. The phrase #diddygethard has taken on this weird emotional meaning for me.

And there’s a bunch of people on Twitter who never gave up either. When the date for this month’s show was announced, they reminded him.

One morning I woke up to 14 voice mails. It turns out Diddy had sent me a tweet telling me to wake up because he wanted me to call him — because he wanted to do the show this month.

I called him at 9:30 in the morning and he picked up. He said he was into the show but that my date of the 15th was a little tight because he might have to present at the Golden Globes in LA the next day. I was like “Wow, your life is different than mine.” And he was like “What about the 14th?” And I was like, “Yeah, I think that will work,” and he said “Congratulations. One hundred percent. I’m your good luck charm, motherfucker. Never forget that.”

And then he hung up the phone.

Of course, on Saturday I’m launching a 12 day cross country tour with the cast of my show. We’re doing six shows in 12 days and it’s been this organizational and logistical nightmare and I’ve never worked harder on anything. I’ve already been completely overtaxed and stressed out. Diddy wanted Friday.

But I said “Fuck it, I can organize the Diddy show on top of that.” So now Diddy is officially launching my cross country adventure (which you can read about here at Splitsider with a daily road journal I’m doing, at my website and on Twitter if you follow the hashtag #AmericaGethard).

So tonight, at long last I’m doing my show with Diddy. It sold out fast and a lot of people are excited. I’m excited too, but I’m also overwhelmed, exhausted, and really, really scared.

I’ve spent a year trying to do a show with Diddy. Now I just have to figure out what to say to the guy.

Chris Gethard is a comedian from New York and the host of the Chris Gethard Show.

How I Convinced Diddy to Do a Basement Theater Comedy […]