The few hundred people huddled inside The Sinclair clutching their PBRs are watching The Okay Win with the kind of easy temperament that greets most opening bands. It’s a mixture of cool relaxation coupled with mild appreciation, subtle head nods, end-of-song applause and all. They like what they hear, but the band is not the night’s main draw.

But while those in attendance might not know it, a great story is unfolding onstage before everyone’s eyes. After a near-constant string of unanswered emails sent trying to book shows in an already crowded local scene, The Okay Win somehow stumbled into the show of their dreams opening up for Stephen Malkmus and the Jicks. Malkmus was booked to play an aftershow following night one of Boston Calling on September 25, and Bowery presents tapped the band as the night’s opening act only 24 hours earlier. We caught up with front man Stephen MacDonald to talk about how the band’s struggle to find gigs nearly broke them, and how the show with Malkmus helped reverse their fortunes.

How did this all happen?

To be honest it was kind of random. Bowery Presents, they book The Sinclair. I’ve known them for years because they also book Great Scott. I just wanted to build a rapport with some of those guys. A few years ago, back in 2011, we got to open up for Kevin Devine at Royale, and through that I got to meet one of the other guys at Bowery. I’ve always stayed in touch with them to put our name out there in case anyone needs an opener, but it never works. I emailed some of the guys about three shows that were scheduled for November and December at Great Scott. I told my drummer, you know, “This is it. If they don’t reply I’m done trying.” I didn’t know what to do anymore. I thought it was over for us.

You came that close to ending it?

Yeah I mean, we’ve gotten very lucky. We’ve gotten to be the local opener a bunch of times and we’re grateful for all of our opportunities. It’s hard, it’s very hard. Part of it I think is the kind of person I am. I don’t live directly in the city, I’m married, I’m in grad school, so I’m not out every night at shows. That’s kind of a hindrance to us being able to do stuff. It’s not as easy as it used to be to get shows. I remember it was a Wednesday night. I was sitting with my wife and told her, “I think the band’s over.” She said, “No, I think something good will happen. I bet you’ll get a big show.” The next day this guy Josh from Bowery emailed me and said, “How about you open up for Stephen Malkmus at Sinclair tomorrow?” I was at work at the time. I emailed him back like, “Holy shit, are you serious? Is this a joke?”

Was it all hands on deck at that point? Did you just have to drop everything to practice and get ready?

I was shaking. It was funny because we have a band text message thread. The last message on the thread was Adam, our guitar player, seeing if we wanted to go see Stephen Malkmus. The next text was me saying, “Hey guys, we got asked to open for that show.” It was a funny turnaround from thinking we weren’t going to get any shows to what for me was the biggest show I’ve ever played in my entire life.

When was the last time you had played or practiced together at that point?

This summer has been really tough. The drummer who played with us for that show, he was the original drummer in the band. In 2010, he left. We had another drummer since then up until this past June. He had a kid, so he left. Right after that we got asked to open for The Ataris. I don’t know if you remember them.

Sure.

They were doing a tour behind one of their old albums, and we got asked to open for them the day after our drummer left. Matt, our original drummer, had to jump back in and relearn everything. But to answer your question we’ve had a few shows this summer, and each one we had to practice the day of the show to get ready. We all have full time jobs, and our bass player lives in Western Mass now. When this happened, we hadn’t played in the same room since July. Everyone dropped everything they were doing. People called in to work, so we threw everything for a loop.

Did you turn around and run through your set that night?

We actually only practiced for 20 minutes before the show. We booked a pay-by-the-hour place to practice from 5 to 6. We figured we’d practice the set once and then go to the show, but the people who run the space showed up a half hour late to let us in. We literally ran in and played our songs. Some of the songs we played that night we hadn’t even practiced. It was like, “Whelp, let’s just see how this goes.”

Playing with Malkmus seems like it would give you an interesting out in that regard, though. A loose or shaggy set kind of fits the bill.

Oh yeah. Our bass player Ryan brought that up. He was like, “If we go up there and fuck up, people are gonna love us.”

What happens when you get to the venue?

Normally the places we play, like TTs, Middle East, or Great Scott, you load in all your own stuff and everything. But The Sinclair couldn’t have been nicer to us. We were nervous going in because they deal with major touring bands all the time. We were afraid they’d see this little local band and think, “Who cares about these guys?” But they were so nice. They helped load our stuff in, set us up for sound check, gave us food and drinks, gave us a green room, just all this stuff you never get. Usually they just hand you drink tickets. They were super attentive, more than we could have asked for.

We went over to the kitchen for food, and Malkmus and his band were sitting right behind us. I couldn’t even look at him. We’ve played with Kevin Devine, we’ve played the House of Blues. But to me he’s just such an icon.

Had you seen him before, either with Pavement or the Jicks?

I saw Pavement once in 2010. I’m 30, so I was too young to be into Pavement growing up. I never got to see them in their heyday. He’s on the level of somebody like Springsteen, to me personally. Seeing him, I just didn’t know what to say, so I didn’t say anything. I didn’t want to freak out and make a fool of myself before the show, so I left him alone.

Before the show, we went and hung out in back. They had their green room and we had ours. Their door was shut the entire time. He came out to grab a guitar and we made eye contact. Again, I didn’t say anything, neither of us did. I started to think, “Man, I’m going to play this show and not say a single word to him. I’m really gonna miss out on this opportunity.” We went out and played the show, then I watched the set and loved it. Afterward we saw the door to his green room was open. His guitar player invited me in. I still can’t believe it happened. [Stephen] was very complimentary of our set and thought it was rad. We just started talking about school, how we had the same name spelled the same way. I was present, but at the same time I thought, “I can not believe this is happening.” It was unreal.

It’s cool because they didn’t have to do that. They could have packed up and split without a word.

We’ve played shows where the touring band really couldn’t give two shits who you are, because they play with a different band every night.

Right, like it’s not worth the time to get to know you.

Exactly. They didn’t have to say a word to us, so it was super nice of them. My worry was I was going to gush, but we just talked and got to know each other.

It’s a weird thing, like, “How do I talk to this person like a normal person?”

Yeah, because you want them to look at you like a peer, not like a fanboy. Not that talent wise I’d ever get to his level, but I just wanted him to recognize me as another guy who’s trying to do it, a guy who loves making music.

What are your favorite records of his? Are there ones you keep coming back to more than others?

When I was in high school, I worked at a mall down by Plymouth. I worked in an FYE. We’d get these monthly mixes from corporate, and one of them had “Spit on a Stranger” on it, but it was by Nickel Creek, who’s a country band. I just thought, “Wow, this song’s great.” Then during the days of Napster and whatever, I found out it was a Pavement song. Once I got into college, I started falling out of the pop punk stuff and started getting into different things. Pavement and Kevin Devine were the big two bands for me. Slanted and Enchanted was great; I love the song “Here.” Admittedly, some of the stuff is a little too grating for me, but the songs that do hit it are amazing. There’s some songs I just want to live in. The feeling it gives me, I want to live in that feeling. That’s what a lot of Stephen Malkmus’ songs are to me. Crooked Rain, Brighten the Corners,albums like that are just so good.

There’s definitely a strong Pavement influence to your songs. Not in a derivative way, but you can tell it’s a point of inspiration.

Yeah. I always get from other people that I sound like Malkmus. I sing in sort of a talky kind of way like he does, so that’s a major influence. Growing up, everyone from Aerosmith to whoever had singers with these huge, powerful voices. Malkmus made me realize that you don’t have to have a great voice. A lot of what he sings is jibberish. But if you sing it in an honest way where people believe what you’re doing, that’s what it’s all about. That’s where I take most of my musical inspiration from him is vocally. He made me realize I could be a singer if I tried.

Did doing that show give you a second wind? Is it a shot in the arm?

Oh definitely. The history of our band, it’s always been an ebb and flow situation. Any time we get attention, I kind of freak out about it. All of a sudden I feel like I have to live up to something, my own expectations, and I retreat. I just take the band and hide for six months. But we’re still on a high from this. Even as we talk about this now I’m shaking. I’m so revved up. We’re looking for more shows, we’ve gone out and gotten our own practice space, we’re doing new merch, we’re gonna repress some of our records. We can’t do this all the time, but we want to ride this wave as much as we can. I’m really proud because we got this show on our own merit. It was all about staying in touch and making connections. I don’t have any disillusions about being a huge band, and I don’t know if I want to be one. But if people think to themselves,”Oh, the Okay Win. I dig those guys,” that would be awesome.

It’s really a great story.

I’ve had a lot of bands come to me and ask how we get some of the shows we do, and I think it’s really just about being nice and answering emails. If you’re a band and someone emails you about a show, just take two seconds and respond. Little things like that go a long way. Persistence is big too. It can take a long time, but maybe one email leads to a show, then two, then three, and then you’re opening up for one of your idols.

THE OKAY WIN W/ BIG BIG BUILDINGS, PASTURE DOG. THU 10.15. 8PM/ALL AGES/$10. OUT OF THE BLUE TOO ART GALLERY, 541 MASSACHUSETTS AVENUE, CAMBRIDGE. 617.354.5287.