Travels with Kyle, Dispatch #1: Los Angeles and Las Vegas

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“Finally, Mustard.”

It seems weird to have a password to get into a comedy show, but that’s what you had to say to get into RBar in Los Angeles’s Koreatown on Tuesday night. There was no cover, cheap beer, and a lineup of a dozen comedians trying out new bits and sharpening their jokes. One of them was the man I’d come to see, who I will be spending the next two weeks on the road with for his Great Mistakes Tour: Kyle Kinane.

For those who don’t know Kyle, he’s a 34-year-old LA-based comic who’s been doing stand up for over a decade and has had a hell of a last couple of years. Death of the Party, his debut album, came out in 2010 to rave reviews and was named one of the top ten comedy albums by The Onion’s AV Club. The man himself was named one of Variety’s Top Ten Comics to watch. He has opened for the likes of Patton Oswalt and Aziz Ansari, and he recently toured with Daniel Tosh. His first headlining gig was May of last year.

Kyle opens his set by talking about his recent DUI and subsequent 12-hour stint in jail. I was surprised to hear him joking about so recent a calamity. “That’s just how I process things now,” Kyle tells me when I ask him about it later. “My stuff is pretty personal and I want something to talk about. My comedy is getting to the point where it’s more conversational, and that’s part of the conversation. I’ll feel better talking about it.” The crowd feels better, too: he leaves the stage to the sweet sound of whistles and applause.

Not long after Kyle’s off stage we head out. It’s unlike either of us to call it an early evening, but we’ve got a long trip ahead of us. The Great Mistakes Tour of 2011 will take us from LA to Las Vegas; Boulder; Sturgis, South Dakota (where the 71st annual Sturgis Motorcycle Rally will be taking place); Omaha; and then, finally, a six-hundred-seat venue in Sioux Falls.

“There’s no way I’m filling that place,” Kyle says. I, personally, am worried about just making it there. Neither Kyle nor myself are known for saying no to trouble (“life mistakes are my co-pilot” is a personal motto), add that inquisitive nature to long stints of driving during the hottest month of the year, a love of all things alcoholic, and the fact that I thought it’d be funny to bring a Buck knife named “The General” that I bought off a gentleman on the street and you’ve already got some red flags. Not to mention the fact that the bikers who attend the Sturgis Rally aren’t known for their hospitality.

But in Los Angeles that all seems a long way off. The next morning we pack a few bags, toss them in the back of Kyle’s white Ford Ranger truck, and head off into the desert.

* * *

When we hit Las Vegas the sun is still in the sky and city has not yet begun to sparkle. We check in at a railroad-themed casino/hotel that’s off the strip and within walking distance of the venue. The gig that night is at Boomer’s Bar, a locals’ joint on the outskirts of town, where it’s easy to imagine the bodies of thousands of luckless gamblers and Vegas natives buried under the sand. The only other business on the block is “America’s First and Only Heavy Equipment Playground,” Dig This!. It’s exactly what it sounds like: an expansive sandy lot filled with giant tires, road cones, and backhoes for rent; oversized tonka toys for tourists excited to part with their dollars.

When we walk into Boomer’s I’m surprised by two things. One, I’ve been in San Francisco for so long I forgot there’re still places where you can smoke indoors in this great country of ours. The second thing: save for two dudes with ponytails and the bartender, who’s busily texting on her cellphone, there’s nobody in the joint. Kyle and I stand in front of the black plywood stage and its lone, depressing microphone as our eyes adjust to the gloom.

I walk up to the bar and order two Buds, thinking that naming this “The Great Mistakes” tour was maybe a bit too apt. I’m a rookie at the life of a touring comedian, though. Kyle just shrugs and says, “Let me see if there’s something in the back.” He disappears through a door I hadn’t even noticed. On the other side, the room is packed.

When the MC asks if anyone’s from out of town only one woman from Wyoming cheers. Other than that, it’s all Vegas locals. The crowd is young, made up of girls in short shorts and guys in baseball caps and polo tees.

The opening acts get the crowd going. These comedians are like so many all around the U.S., folks in the back-rooms of bars and basements of churches working hard for laughs. That’s not to say that their comedy isn’t unique — the stories are very Las Vegas, featuring large sums of money coming and going just like they’re doing in the casinos on the other side of the highway. And the crowd is fantastic: no heckling, just a room full of people who came to the back of Boomer’s Bar to laugh.

When Kyle gets onstage he looks out over the crowd and says, “Well, here I am, the last float in this broken people parade that is comedy.” He then entertains everyone in the room for over forty minutes with nothing save four stories, slow burning as the locals do nothing but laugh and listen.

Afterwards one of the fans calls the night “a monster of a show.” We’ve spilled out into the front of the bar to clear the room for a small group of older drinkers lining up to see a late-night magician. Out here, Boomer’s is all cigarettes and slot machines. We sell some of Kyle’s CDs, talk (there are many other comics in the room, and I’m learning that comedy is a favorite topic of conversation amongst those who practice the art), and meet many of the pretty women who were in the audience, all of whom are also wives.

Like any rockers on the road in Las Vegas, we end our night with In-N-Out burgers, then weave our way back to our railroad hotel while playing an impromptu game of “Shake Time Shakedown!,” which entails nothing more than Kyle yelling the game’s name and attempting to slap my vanilla shake out of my hand.

The next day we head out for Denver. The billboards for Little Darlings strip club and all-you-can-eat buffets give way to the red desert sands and rocky crevices of Arizona and Utah. “I’m so fortunate,” Kyle says, pointing to the landscape. “Doing comedy lets me see all this.”

Both of our windows are down despite the desert heat, which makes the highway look like it’s turned to water; a reflective, glassy blue that retreats before us as we drive toward the Rocky Mountains.

-Dispatch #2: Boulder, CO and Sturgis, SD

- Dispatch #3: Omaha, NE and Sioux Falls, SD

Isaac Fitzgerald has been a firefighter, worked on a boat, and been given a sword by a king, thereby accomplishing three out of five of his childhood goals by the age of 25. He has also written for AlterNet, The Bold Italic, McSweeney’s, the San Francisco Chronicle, and Mother Jones. He is the managing editor of The Rumpus. Follow him on Twitter.