Comedy is tough, but Patton Oswalt makes it look easy.

The Emmy and Grammy-winning comedian has released eight comedy albums and six stand-up specials. He’s also appeared in more than 50 movies.

By 2016, Oswalt had planned to take a break from stand-up when his wife — true-crime author Michelle McNamara — died unexpectedly.

Suddenly, comedy got much, much harder.

Oswalt eventually returned to the stage, finding a way to talk about grief that was moving and funny. He released his latest comedy special, “Annihilation,” last year.

I think [the name] ‘Annihilation’ was a combination of a lot of things because it was about how I was feeling, how I was existing. I felt like I just didn’t really exist. I even talk about, you know, am I the one that died? I was in such deep grief. And also, I was kind of making fun of the idea… part of comedy language is, oh my god when you have a great set, “You killed! You destroyed! You annihilated them!” So I was almost mocking myself for [going] back on stage a year after my wife has passed away and [doing] comedy about it. There’s something so absurd, so I just decided to use very elevated, hyperbolic language to talk about it – to say that’s the only way I can deal with the ridiculousness of it.

Oswalt says finding the space between humor and hardship was a “slow process.” At first, he would go to open mics just to get out of the house.

I didn’t know what else to do. This is what I’ve done my whole life, so I started doing open mics around Los Angeles and luckily there’s such a great wave of young comedians right now with shows that I could go up on stage and just sort of experiment around. So, first it was just out of pure survival: I’m just going to go on stage. I don’t know where this is going to go.

At first, he tried working on routines that didn’t mention McNamara. But he says it became less awkward when he talked about his grief on stage.

There were a couple of nights when I was working on the special where I chickened out and thought maybe I shouldn’t talk about this at all. And I had worked up an hour that never mentioned my wife passing, never mentioned my grief. It was just an hour of jokes and those nights were super uncomfortable for the audience because by going up and never addressing it — even though not all of the audience knew what I’d gone through, but enough of the audience — was the height of discomfort.

Oswalt is no stranger to being raw in his comedy routines— he’s tackled personal subjects before, such as his struggle with depression. But “Annihilation” was something entirely different.

When I talk about the embarrassing things in my life like my years of depression or the time I got a prostitute and it went horribly wrong, I was always talking about it from the point of view of someone that had come out the other side and was either managing and laughing at the memory or had found a way to live with this thing that was never going to go away totally. Whereas in “Annihilation,” I’m talking about an awkward subject that I have absolutely not come out the other side of. I was still very very deep in mourning.

“Annihilation” touches on other topics, too. Oswalt reflects on the way our political climate has shaped what it means to be a comedian today, and how keeping up with a heavy news cycle can be daunting.

Maybe one of the few upsides of Trump being president is that it will forever explode the cliché that when things are bad, it must be great for comedians. When Bush was president, I got at best ten minutes of material from him and I would have gladly given that back if we hadn’t been torturing people and our money hadn’t caught fire. And now [with President Trump], there’s too much stuff. The grist is choking the mill at this point. I can’t process it fast enough.

Text by Kathryn Fink, show produced by Paige Osburn

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