Emmett Montgomery doesn't try to bowl you over with his comedy. He's not going to yell his jokes at the audience. He's not going to wildly gesticulate. He's not going to deliver a rapid fire barrage of one-liners. His brand of humorous standup storytelling feels as authentically warm as a cup of cocoa by the fireplace on a cold winter's night. You just want to curl up in the awkward moments he shares and laugh the night away. (Disclaimer: Emmett Montgomery Co. takes no responsibility for any scalding that occurs while uproariously laughing with hot cocoa in hand).

Over the course of the last decade, the bearded 38-year-old standup has become a stalwart of the Seattle comedy scene. In addition to his own act, he's also established shows like the monthly Weird and Awesome at Annex Theatre and the weekly The Magic Hat at Rendezvous to give other performers a welcoming platform to show off their own eccentricities. This month Montgomery turns Weird and Awesome into a platform for recording his (long overdue) standup album. The recording will be for ASpecialThing Records, which has put out standup albums by Marc Maron, Bob Odenkirk, Jen Kirkman, Wyatt Cenac, and many more top comedians. If you'd like to have your laughs live forever alongside Montgomery's jokes, attend one of the three Weird and Awesome special recordings at Annex this weekend (June 11 and 12).

For our latest Fiendish Conversation, we chatted with Montgomery about the long path to the album recording, the strength of Seattle's comedy scene, and tontines.

What are you looking forward to most about finally recording the album?

This is something I have essentially been working on for about four years. I’ve kind of had this hour, what I felt has been the perfect hour. ‘Cause sometimes you’re on stage and just wonderful stuff happens. You have this moment where it’s almost like bullet time from The Matrix: you know you feel all the words falling out of you, and as they are, you can almost stop and turn them around. You feel just extremely connected with the audience and everything as you’re telling your poop jokes. And when you have one of those, you’re like I want this to last forever. So I’ve been thinking about that a lot. In the last four years, since I had that first moment of yeah, I could have at least 50 minutes of something to say, that perfect hour has changed, but things are really good right now.

I actually recorded an album in the backroom of a Thai restaurant, but for several reasons, it just wasn’t the right thing. Out of the three shows, there wasn’t a perfect moment, and all the shows edited together didn’t quite mesh.

I was gonna go ahead and do one myself this year. I was talking to the extremely cool Erik Blood, and he was gonna help me produce an album. But then I was doing San Francisco Sketchfest, opening for Baron Vaughn. And it was the day before he was going to record his album in Portland, and Ryan [McManemin] from ASpecialThing was there. He has a real great podcast called Put Your Hands Together that I had been on a few years before. He had edited that podcast, so he recognized the joke I told. So we started talking and we had a real, real great conversation. I don’t know if you’re familiar ASpecialThing, or why it’s important to comedy, but it started out as a message board and then it evolved kinda into this boutique label. And everybody who they have done albums for are either people that I’ve had adventures with and love on a very like deeply personal level or people I love onstage. And so the thought of being on that is super cool. I try to do things kind of based on emotional connections, sort of community-based, and that’s what it feels like being part of this label.

And Ryan wanted to do it out here in Seattle. So doing it in Annex where I’ve had a show for five years that I produce with my wife, with the team of people who’ve helped me and who inspire me being on the show, seems real fun.

I have an older brother who is kind of one of the kings of the one-inch mountain of rock n’ roll in Salt Lake City. He’s always been a real kind of obscure but important musician to people. I think I’ve always been jealous of the way my mom has doted over his albums, and forced the ladies of the Relief Society to listen to ‘em. And I want that.

And maybe if they need to send a comedy album into space, this could be it.

Have you done anything special to prepare the material?

I headlined a really lovely theater on Bainbridge Island, Bainbridge Performing Arts, and I ran the hour there to sorta decide what jokes would work and what to take out. But I feel like I’ve been working on this long arc for a long time. So I’m kind of ready for it to be done, and stop looking at it so big. I have a 20-minute joke about meatloaf, which is I guess gonna be a big chunk of it. And then I talk about my nightmares, my wife, and the other things that are big parts of my life. But it should be interesting ‘cause normally [last] weekend we’d have a Weird and Awesome and it would’ve be my big birthday show. We’d have the tomato soup cupcakes and stuff.

How would you describe Weird and Awesome to those unfamiliar with the show?

Originally it was supposed to be a comedy showcase where I’d have a bunch of different types of comedy, and it’s not that. It’s a good thing and it makes people feel better. Sometimes it’s not even a comedy show. Sometimes people cry a lot. I think it’s like a safe space to fail, and a real great place to succeed. I have a spiel I do at the top of the show, and it’s kind of my love letter to Seattle and all the things happening inside of it. So I guess that’s sorta how I describe it.

And we are going to be doing kind of little Weird and Awesomes before the recording. We’re going to do the Song and Story and Sharing segments featuring the people who have been a big part of the show. So Allison Lizotte, who works the door and is a great local comedian as well, will be showcasing her haunted dollhouse museum at one of the shows. And the cartoonist Ellen Forney, someone I find really inspiring, will be telling a story on one of the shows.

Do you feel like Seattle comedy is in a pretty good place right now?

I think there are some really exciting things happening right now. I’ve kind of seen it all. I mean we get a lot of people that get really good really quick and then leave to other places, which is fine. Then some people stay and continue to do wonderful things. I think right now there are a lot of really beautiful independent comedians and producers kind of coming to bloom.

This new generation isn’t just standups, a lot of them are very cross-genre: they’re storytellers, or do improv, or write sketches, and that’s really exciting. Because when I started, it was pretty much standup or bust. And I got a lot of flack for not fitting into that hole, but I think its also one of the reasons why I have survived and why I’ve had some of the opportunities. So I like the fact that there’s not just one best show or one group that kind of dominates it all. There are several scenes, and audiences and comedians can pick and choose. As a consumer and a participator, you still have to explore it and find these kind of wonderful caves of art. I think its always been that way with Seattle. Maybe it needs to change as we have more and more new people living here. Maybe we need our neat stuff to be more accessible to folks. But that’s a completely different conversation that I could have for hour.

For right now I’m really, really happy with what’s going, especially the amount of diversity. Comedy Womb started a few years ago, and its goal was to bring more women into standup. And a handful of people who started there have kind of graduated from the open mic scene and are now on their way to becoming very talented and hardworking people. We have a pretty large queer scene. I mean its still small, but it’s bigger than most cities. We’re getting a lot of different voices, cause we’re kinda helping change sort of the stereotypes that standup is just a bunch of sad bearded dudes. But there is room for those guys too, fortunately for me. [Laughs]

Nationally there’s a lot of change happening I think comedy is both very easy and difficult to do right now, cause the big path of success which may or may not have been real—you know, start working at the clubs, and get noticed, get on Carson, and there we go, you have a career—is just not real now.

You have to be very creative to make a living at it. There’s a handful of really strong kind of headliners that work locally and nationally: Derek Sheen, Brett Hamil, Elicia Sanchez, Kortney Shane Williams, myself. Both Brett Hamil and Derek Sheen released great albums this year, so Seattle is actually pretty good at contributing to the national scene. So my goal is kind of to be able to contribute to that, like another great Seattle album. Plus, there’s the great generation of veterans who have been doing it for decades: Kermit Apio, Brad Upton, Cathy Sorbo, folks like that. But this kind of new generation is real, real neat. They’re doing some real stupid and wonderful shows.

This is the first year that locals and nationals will be on the same bill at Bumbershoot, which is something I’m very excited about. I got to have some insight by kind of working with them on the program.

Also, you know, open mics are real gross. The problem with standup, or just comedy in general, is you can declare yourself a comedian and people will give you the benefit of the doubt. But sometimes you’re just a monster with a microphone. Cause if you actually want to be a doctor, somebody has to show you how to be a doctor. But then everybody doctors the same way, hopefully, where comedy is kind of its own path. And I think that when people look at Seattle comedy, they have to look at its extremely large and active amateur scene—which is the open mics—and then maybe look at the smaller, more refined, but still very beautiful professional scene. The journey from one to the other is real long for some, and intense.

And in addition to the album recording and the regular monthly Weird and Awesome, you also still host the weekly The Magic Hat show on Mondays at the Rendezvous, right?

Yeah. If you wanted to see why I am excited about what is currently happening in Seattle comedy, that’s a good [show to check out]. It’s not just standup, it’s storytelling, and characters, and you know.

Sometimes we do this thing called secret party where we turn off all the lights in that basement of the Rendezvous and I give people five minutes to declare their secrets. We enter a tontine, which is a treasure pact… like Abraham Simpson and Montgomery Burns are members of a tontine over Nazi [paintings]. The whole idea is this thing of value can only be redeemed if you’re the last living member. So we enter into a tontine over these secrets and, man… when those lights go off and the secrets come out—not just from the performers but also the audience—you realize that you kind of live in a strange and beautiful place. That’s what I want to do—create a strange and beautiful place.

Weird and Awesome: Emmett Montgomery Album Recording
June 11 & 12, Annex Theatre, $10