The first time Indianapolis native and "Big Lebowski" superfan Tom Esterline, Jr. saw the 1998 Coen Brothers cult classic, well, he fell asleep.

"I’m pretty sure I passed out and didn’t see the movie all the way; it was an after-work viewing on DVD," Esterline, Jr. recalled. "It was only because I was tired, and it was very confusing to me, waking up and falling asleep and waking up at the end; the whole nihilist thing was blowing me away. I watched it again within the week."

And he watched it again. And again. And again and again and so on until he eventually reached well over 100 viewings. He’s now a superfan – an Achiever, as they are called – replacing "You’re welcome" with "The Dude abides," as well as becoming one of the most recognized faces at Lebowski Fests across the nation – mostly because that face comes shaggily dressed, as many are, like Jeff Bridges’ iconic character role of The Dude.

Decked in his finest Pendleton sweater, Esterline, Jr. attends as many Lebowski Fests as possible – and the next one on deck is this weekend is right here in Milwaukee on Friday, Aug. 21 and Saturday, Aug. 22 at Cathedral Square Park.

Before the credits and bowling balls roll this weekend, OnMilwaukee.com got a chance to chat with Esterline, Jr. to discover where his love of Lebowski came from, why the film still lives on and the lotta ins, lotta outs and lotta what-have-yous behind his Dudeness likeness.

OMC: What introduced you to "The Big Lebowski"?

TEJ: What got me going on it was that back then I was bartending, and a co-worker of mine came up to me and said, "Dude! You’re The Dude!" And I was, like, what the f*ck are you talking about? He says, "‘The Big Lebowski,’ man!" I’m like, OK, whatever. He saw it in the theater and comes and tells me this. So I have to wait for the DVD to come out, and he’s calling me The Dude for six months or more before I see it.

OMC: Even with that first failed viewing, it still obviously stuck with you. What about the film resonated with you, and keeps resonating watching it over and over again?

TEJ: Well, the whole buddy thing that some people refer to, where you have a Donny and a Walter and a Dude, it’s kind of the interaction I have between me and all of my friends. I was in a three-piece band, and we had a Dude, a Donny and a Walter in the band. Everyday life is portrayed in "The Big Lebowski," and vice versa.

OMC: When was the moment when you decided you wanted to dress up like The Dude? 

TEJ: Another guy I worked with at the bar said they were taking Lebowski Fest to L.A. I had already gone to my first Lebowski Fest in Louisville, which was the third annual in I guess 2004. He said, "Let’s go," and I thought, well, OK, he’s a good Walter; he’s kind of a heavy guy. So he kind of talked me into it, and I’m like, well, if I’m going, I’ve got to dress up. Everybody dressed up for the one in Louisville, and I didn’t; I just kind of wore an In-and-Out Burger shirt to my first fest.

I already had The Dude thing going. I had this huge beard, so I kind of went as this really enhanced Dude because I had this eight-inch long beard. I had a Dude sweater that I bought on eBay for, like, $38 or something. I put this half-assed version of what The Dude would wear together, and I did alright. It wasn’t my goal; I was just kind of in the mood and in the mode, I guess.

That was my first attempt, and everyday for the next three years was focused on improving on that. (laughs) Granted, I kind of gave up after about six years ago; I kind of said, "It’s just a representation, man. It doesn’t have to be perfect."

OMC: What was the hardest part to get for the costume?

TEJ: The hardest thing was figuring out the sunglasses The Dude has. I was able to do it; it just took forever. I guess they call them square aviators. That was a hurdle for me, because I just wore some big aviators the first time, and I got a pretty good awful picture from that L.A. trip. I met Liam, the guy who plays Liam; that’s where I first met him, and I’ve become pretty good friends with him. We keep in touch. It’s a whole world of Lebowskis. Keeps me going.

OMC: I would think the hardest part would be the sweater because it’s such a particular design.

TEJ: At first, nobody knew what they were looking for. I figured it out; I did lots of research and bought all of the books that talked about the movie – at the time – and there was one that had a chapter on costumes. You find it on eBay, you find similar ones, you narrow it down and you wait for one you can afford I guess. Back when I first bought mine, I bought more than one. They were pretty cheap, but as time went on, they got more expensive, and people started paying $500 or $1,000 for them. Then Pendleton released a re-issue of the sweater, which it’s the equivalent, and they even make one in a bigger size.

OMC: Do you have any pro-tips for anybody going to Lebowski Fest this weekend?

TEJ: My best piece of advice is just to take it easy, man. No aggression will stand at Lebowski Fest. I think if you’re going to the bowling party, try to dress up, and if you have no costume, wear all black and go as a nihilist. At least you’re participating.

OMC: Do you ever think "The Big Lebowski" will ever become so popular that it’ll lose its niche as a cult classic?

TEJ: I think it’ll have ups and downs, strikes and gutters. Corporate America can ruin it by trying too hard. There’s nothing wrong with corporate America, but why latch onto the good stuff and ruin it? Let it be what it is. It’s kind of why the Coens haven’t brought out a second movie. They’d probably do a good job, but it’s better to let it stand alone. I never bought any of the t-shirts, the official "Big Lebowski" t-shirts. I like the whole Dude lifestyle. People give me things that are corporate made; "Hey, this made me think of you," and then they give you a t-shirt they found somewhere on a clearance rack. It kinda sucks when "The Big Lebowski" makes the clearance rack.