Josh Gondelman on Comedy and Writing for “Last Week Tonight”

This week I sat down with comedian and general mover and shaker Josh Gondelman. I started following him on Twitter a few years ago and he’s gone on to do awesome stuff, from co-running the hilarious account @SeinfeldToday to publishing You Blew It!: An Awkward Look at the Many Ways in Which You’ve Already Ruined Your Life in collaboration with his pal Joe Berkowitz of Fast Company. Now he has an awesome gig as a staff writer on Last Week Tonight with John Oliver, a show that has made me applaud at its brilliance. He’s a hilarious writer and an all-around incredibly nice guy. Thanks for coming on the show Josh!

Get to know Josh more below. (Oh and make sure to subscribe on the iTunes Store and on Sound Cloud!)

How did you decide to become comedian? Who inspired you?

I always loved jokes and comedy, and my friend Joe Smith (his real name, I swear) started doing standup around Boston, and my friends bullied me into following my dreams too.

What’s the writers room like at Last Week Tonight? 

It’s really great. Everyone is so funny. There are a lot of very silly riffs and recurring characters that never make it on the show but emerge when we’re all writing together.

What tips do you have for people who want to be funnier on Twitter?

“Good at Twitter” is such a funny goal. I’d say be consistent and also do what you think is funny. On the internet you get to be more weird and specific than you can be with a live audience.