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Josh Gondelman on Googling himself, ruining holiday parties

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For someone who literally wrote the book on how to ruin your life, Josh Gondelman is doing pretty well for himself. 

As a writer for Last Week Tonight with John Oliver, Gondelman recently wrapped up season two of the critically acclaimed HBO program, and will be returning for a third season this February. As an author, he released his first book, You Blew It!: An Awkward Look at the Many Ways in which You've Already Ruined Your Life, along with co-author Joe Berkowitz, where they examined the seemingly obvious yet constantly committed societal faux pas including everything from meeting new people (do you shake hands? Fist bump? Both?) to small-talk fails (if you don't know something, just pretend like you do). And as a comedian, he's preparing to record his second album later this month. 

Despite his insanely busy schedule, Gondelman will swing by Comedy Corner Underground this Friday and Saturday for three shows alongside local comedy heavyweights Cy Amundson and Mike Lester. We caught up with the comedian/author/writer/failure expert to chat about Googling yourself, postpartum depression, and how to ruin your upcoming holiday gatherings. 

Just curious, when was the last time you Googled yourself?

Embarrassingly recently. I can't remember what came up though.

One of the first auto-fill results is "Josh Gondelman girlfriend."

That's hilarious. I think that probably happens because people know that my girlfriend is way cooler than I am. They see me and they're like, "Well, he's loud, and she's smart and accomplished. Let's see why she's with him." When females get famous, guys are always Googling their feet or something gross. I think that as a male public figure, having people Google me to check out my significant other means I've made it. 

You definitely have a lot going for you right now. What's been keeping you busiest?

It's been a great month and a half. The book was released in October, Last Week Tonight just wrapped this past month, I've been doing a lot of standup, and now I'm getting ready to record a new album here in December. 

It's been several years since your last album. Why did you decide now was the time to record something new?

I've been thinking about it for a long time, but I've been so dialed in with my job that I really hadn't had time to get in some good, longer sets. The other thing is that when the book came out, I did a ton of press focused on that. There was tons of excitement around it, which was great, but then it all sort of evaporated quickly. It was almost like having postpartum depression, and I needed to create something new once that wave of excitement around the book was over. 

How hard has it been to work on material for this new album?

I think the hardest part hasn't been writing new stuff, but waiting to actually get onstage and try out some new bits. In a perfect world I'd be able to be performing all of the time. Instead, whenever I'd have a week off I'd shake a new bit loose and then have to pounce on it and seize it so that I didn't lose it. 

Now that you've had time to reflect on the release of You Blew It! are you happy with how everything came out?

I was very pleased with the final product. It was sort of the result of two years of pitching ideas and trying to find something that Joe [Berkowitz] and I were excited about that a publisher would also be interested in putting out. Once we found it, they really let us have the ability to just write what we wanted. They worked with us on the copy editing and stuff like that, obviously, but no one was sending us notes about the content telling us what was or wasn't funny. It was a really exciting experience. 

With the holidays approaching in a couple of weeks, do you have any tips for how to ruin a holiday gathering?

First is make sure you're too drunk. That's a must. Being too drunk is an easy way to ruin pretty much any gathering. After you're drunk, make sure you ask overly personal questions to any relatives who you aren't close with, and overshare as much information as possible when making small talk. Oh, and be as thoughtless as possible when it comes to gifts. The less effort you can put in, the better. 

Josh Gondelman - Comedy Studio 12.22.12 from Olivia Wingate on Vimeo.

IF YOU GO:

Josh Gondelman w/Cy Amundson & Mike Lester
Comedy Corner Underground
December 4, 8 p.m.; December 5, 8 & 10 p.m.
$12, 18+
Click here for tickets