The Bar Gig Files with Guest, Skyler Bolks "Tall Tales and Bike Trails"

 What happens when a 6'7" comedian, a 1,000-mile bicycle tour, and a lifetime of Midwest stories collide? 

Skyler Bolks, headliner on The Pub & Grub Comedy Tour, talks about life on the road, performing in neighborhood bars across America, writing razor-sharp one-liners, and the surprising inspiration behind his Jokes & Spokes bicycle comedy tour across South Dakota. 

Along the way, Skyler shares hilarious travel stories, behind-the-scenes insights into the life of a working road comic, and why some of the best comedy crowds you'll ever find are in small-town bars.

Whether you're a comedian, bar owner, or just love hearing what really happens between the gigs, this episode is packed with laughs, road wisdom, and plenty of Midwestern charm.

Topics include:

•  Touring the country as a full-time road comic 
•  Performing in bars vs. comedy clubs 
•  The art of writing great one-liners 
•  Skyler's 1,000-mile comedy bicycle tour 
•  Life as one of America's Best Bar Comics 
•  Why small-town audiences are some of the best in comedy 

Grab a drink, pull up a barstool, and enjoy another behind-the-scenes conversation from The Bar Gig Files

Transcript

SPEAKER_01 0:05

Today's guest has one of the most unique stories in stand up comedy today. Stick around for episode number ten of the bar gig five. And even completed a bicycle comedy tour across South Dakota. Let's have a virtual round of applause for Pub and Grub Comedy Tour, Bar Comedy USA Superstar, Skyler Bolks, everybody.

SPEAKER_00 1:15

Hey, thanks for having me, man.

SPEAKER_01 1:18

Yeah, there he is. There's your round of applause. Hey, buddy. I think you know, we've been working together for so long. We we haven't really had very many uh face-to-face conversations, have we?

SPEAKER_00 1:32

I don't think we've ever had any. We've had a handful of conversations on the phone, and that's about as far as it went.

SPEAKER_01 1:38

Yeah, yeah. So this is really cool. I'm glad you could do this. Thanks for being on, man. Uh, and and Skylar's go, he's what you're one of the pub and grub comedy tour originals. Like you've you've been doing this with doing these bar gigs with us with bar comedy, you say, for a long time now, and always get great reviews. Uh, so I appreciate you being on. And I like Skylar too because he's he's from the Midwest, just like I am.

SPEAKER_00 2:09

Yeah, buddy, South Dakota. You're an Iowa guy, right?

SPEAKER_01 2:12

Is there a uh difference that you've noticed? I'm an Iowa guy originally. That's right. That's right. Uh at six foot seven, uh, we always put on the promo flyers, probably one of the tallest comedians you've ever seen. And I gotta imagine that before anyone even hears your first joke, they've probably already formed an opinion. Yep, they've probably already actually some of the wildest yeah. What are there any wild assumptions that people make about you?

SPEAKER_00 2:53

Yeah, I think we've got a little bit of a delay here, but yeah, there's uh before the show even starts. A lot of times people have already come up to me and they've they've asked, they they they don't believe that I'm that tall. They've got to ask questions about all kinds of wild stuff. And the the weirder the bar, you know, the the the drunker they are. So Wisconsin, uh I get some pretty wild questions, some pretty outlandish things that uh not not necessarily G-rated questions that I get from some the some sweet old ladies sometimes, even really like like how do you fit together with uh your girlfriend, or like how yeah, there's like little logistics involved.

SPEAKER_01 3:42

Yeah, yeah, I assume you played basketball.

SPEAKER_00 3:48

I did, yep.

SPEAKER_01 3:50

Okay, cool. Who who did you play for?

SPEAKER_00 3:52

Well, I played so I played uh uh you know in high school and all that, and then I played at a smaller college in Yankton, South Dakota.

SPEAKER_01 4:01

All right, you know, I've got a theory that I've talked to a few other comedians about that some of the best comedians actually come from either high school or college sports backgrounds. And the reason why I have that theory is because if you are operating at a high level in high school or college sports, there's a lot like you've you've got to be able to push through. You probably are getting your balls busted quite a bit by even if it's just your coach yelling at you, and that type of experience helps develop the thick skin that you need for stand-up comedy. Is that something you would agree with?

SPEAKER_00 4:38

Yeah, and there's a little bit, I mean, to be a comic, you have to have some sort of tenacity, you do have to have that ability to push through. Uh, and and it's there is a lot of hard work, and you kind of uh can end up in some kind of uncomfortable situations, not only on stage, but sometimes all the travel involved. Uh, that's another thing that's kind of a good crossover from like athletics to comedy is that you're on the you have to go to the place to go play the other team, and that's what comedy's like too. You know, you have to go, you have it, you're not playing on the home field very often, actually, in comedy. So you're out usually out on the road. So I kind of had a a little bit of a comfort with being on the road like that, you know, sleeping in the back of buses and whatever, whatever needed to be done in order to get there and get the job done.

SPEAKER_01 5:26

Yeah, that's a that's something I hadn't even thought of is that the travel to the away games and sometimes at several hours away, that's also very uh similar to stand-up comedy. Like you you've still got to go through all that travel and then have the energy in order to bring your A game that night. Yeah, that's something I hadn't even thought of. Yeah, so when you're out on the road and let's you're on a long drive to get to the gig, are you are you downing coffee or energy drinks?

SPEAKER_00 6:00

Uh too much of probably both. It depends on what's available. I like I like a good coffee, like I like a good latte. I like to try stuff along the way on the road. Um, and I have my theories about places, like there are certain places if you got the right kind of decor, the right kind of name, like there are some places you can tell from the outside that they've got a good cup of coffee. Uh, but a lot of times, you know, we're going out to the small town Wisconsin, you're probably not gonna pass a Starbucks on the way out there, so your best bet is gonna be maybe an energy drink. You can get a coffee drink at the quick trip or whatever, but you gotta kind of go. Yeah, oh yeah, love love a love a truck stop.

SPEAKER_01 6:51

Yeah, uh, and and you've performed in how many states now so far across the country?

SPEAKER_00 6:57

37. 37. We're working on rounding out those last those last couple. Baker's dozen left.

SPEAKER_01 7:07

Those last 13. Yeah, yeah. The baker's dozen is left. Uh are you are is of of the of those states that are left, which one do you definitely want to get to?

SPEAKER_00 7:19

I Maine. I'm really excited about Maine. Uh, most of the states are actually uh north of uh New York, New Jersey, up in the New England area, and but uh yeah, Maine just kind of is really intriguing to me because it's kind of this uh the from what I've heard, it's kind of a Texas of the north, but it's like kind of got a Canadian flavor, and and and crab. I I like crab, so all of this sounds great to me.

SPEAKER_01 7:48

Yeah, yeah. I've I've done a few shows in Maine, it's beautiful country up there, and I've not heard that analogy before that it's the Texas of the North, but now that I'm thinking about it, that actually probably is a pretty good description, just with a different accent. Sure, yep, yeah, yeah. They they talk more like Canadians, yeah. Yeah, yeah, yeah. What's one what's one thing that you've noticed that all these small town audiences have in common no matter where you go?

SPEAKER_00 8:23

That's kind of tough because it's I mean, people are people, right? People like funny, and you you can go to one town, and a lot of them you you can get away with a little bit of dirtier stuff. Like I can I can pivot into a completely clean show, uh, but it's that part, I guess, doesn't really cross over because every once in a while Dolores from the church group is there or whatever to make sure nobody's laughing at dirty jokes, and then people all kind of check with her because she's gonna say something about it on Sunday or something. I don't know, but I I've had a couple of shows like that. But honestly, I people are just there to have fun for the most part. They don't want they don't want religion or politics in the in the humor, you know, they just want to have a good time, they want to get away from all the things that are happening in the world, and in these smaller towns, too, a lot of times these are like really hardworking people with like pretty tough physical jobs, so there's a lot of farmers and stuff like that. So they just want they just want a night to get away. They usually they the smaller towns drink more than the cities typically, so that's the one big thing that they have in common. And I got a lot of jokes about drinking, so we connect on that level. But for the most part, I think everybody they just want to get away from their daily life, they want to get away from the things on the news, they just want to have a little fun, sit back, relax, and and have a laugh.

SPEAKER_01 9:55

Yeah, that's that's right, it's an escape mechanism, and we're bombarded with that stuff every day, all day on the news and on social media. And I think that people do want to go out for an a night of entertainment to escape all that stuff, so that's a good philosophy that you bring. It's just just give them a fun time, that's all they want.

SPEAKER_00 10:20

Yeah, that's what that's what that's what I think. That's how I look at comedy. A lot of people say comedy has to be a good thing.

SPEAKER_01 10:25

You say you can adapt and give it to clean.

SPEAKER_00 10:31

Yeah, go on, sorry.

SPEAKER_01 10:35

No, we'll continue, continue. We are on a bit of a delay. I want to hear what you have to say.

SPEAKER_00 10:40

Oh, yeah, no, I forgot where I was going with that. Oh, though, uh how I look at comedy, I we're like we're kind of the coach of the fun team. Like, we're here to bring you guys a good time. I don't want to drag you guys down into you thinking about something that's sad or dark or whatever. Like we just I just want it to have be a good time for you to get away. And I've I don't feel like a lot of people think you have to speak truth to power, you have to do this, you have to do that, you have to have a message. And I do have a message, uh, a couple of different messages that I like to push in my show. They're kind of subtle, it's kind of underneath the the top layer. But the number one thing is just be funny. They want to go there, they want to laugh, and so if you can't make them laugh, you're doing something wrong because they wanted that outcome. And I think that's that should always be the number one thing. Just be funny first and figure out things along the way. If you really want to have a message and you can make it funny, sure, but it has to be funny first.

SPEAKER_01 11:49

It has to be funny first, absolutely. And a lot of times the message really could even be something lighthearted, you know, like just always have fun, you know. No matter who you are, where you come from, what your religion is, what your politics are. We all just want to go out and have a good time, and that's how you can actually unite people just with laughter and having fun. It could be on any side of the political aisle or whatever, but when they're in that comedy crowd, they should just be unified with laughter.

SPEAKER_00 12:19

Yeah. And one of one of my messages in the show is I encourage people to be organ donors, and that's packaged into probably the most absurd joke that I do, but it's just it's a fun light that's easy, it helps people, and and we move on from it pretty quick.

SPEAKER_01 12:37

So yeah, yeah, I like that. I like that. Uh and then coming from your your athletic background. What what would you say is more addictive? Getting laughs or winning games?

SPEAKER_00 12:56

Laughs. No question, laughs. No question about it, laughs. Yeah, it's it's a solo activity.

SPEAKER_01 13:07

Uh also your style is built around one-liners.

SPEAKER_00 13:12

So, like, yeah, that because I do a lot of team sports, it's the more individual, it's uh and it's immediate and repeatable, where you can get a laugh and you can get another laugh. If you win a game that feels good for a bit, and then it's a week until your next game.

SPEAKER_01 13:32

Yeah, right. And so if you get a laugh, and then you just get another quick fix and you do that three or four hundred times over the course of an hour. Uh-huh. Yeah. I like that. Uh, one-liners and storytelling, that's a unique style where you combine those two. You don't see that very much. Either a comedian will be a one-liner comedian, or they'll be a storyteller. You do both. Which comes easier?

SPEAKER_00 14:02

Um, the it took a while to kind of develop a better writing process for the stories to punch up the stories and get the jokes built in. A lot of times, you know, people tell a story and it's a long space between the funny parts or whatever. Um, so it took a while to kind of figure out how to tighten that up. The one-liner jokes have always been kind of like quick and easy for me in some situations. Sometimes that you do have to sit down and actually work on writing a good joke, but uh the the the stories come a little bit more naturally. I just had to develop the the strategies that to actually punch up the story and keep it interesting enough for stand-up. The one-liners are usually kind of a fun little thing, like I'll open the show with some just silly one-liners, we'll do some stories, and then I might jump into a couple more one-liners. Some of the stories just end it, the whole story was written to get to a really dumb one-liner that I thought would be fun.

SPEAKER_01 15:08

Yeah, yeah, I like that. I've I've developed a similar style myself where if you can get good at the one-liners, then when you go to write your story and you and you're working on your storytelling, uh, really the story is just a whole series of cohesive one-liners that sort of go together. Yeah, it's all a narrative flow.

SPEAKER_00 15:34

Yep.

SPEAKER_01 15:35

Yeah. Yeah.

SPEAKER_00 15:37

It also, I feel like the this is some the practice of writing headline or one-liners, um, it helps you to tighten up those stories too. Because you start to get used to this like setup punchline, and you get a laugh, you get a tag, setup punchline, laugh, tag. Like, and you get used to that kind of rhythm. And when you're going into a story and things are getting a little too long, it starts to feel really uncomfortable. And you want to get back into that rhythm of and these regular laughs.

SPEAKER_01 16:14

Right. Yeah, I think sometimes that's something comedians miss is they're telling all the details of the story in order to get to like some grand punchline at the end. But the theory that I have is the longer the setup is, or the longer the story is, the funnier that punchline better be.

SPEAKER_00 16:31

Right. Definitely agree.

SPEAKER_01 16:35

You gotta keep it quick. A couple years ago, uh, I was really impressed with this idea when you combined cycling with comedy on your jokes and spokes tour. Uh at what point did you come up with this? With this, I'm just imagining, you know, sitting around thinking that you know what this comedy career needs? You know, you know what the what a challenge that I really need for comedy? A thousand mile bicycle ride.

SPEAKER_00 17:11

Yeah, not maybe not my best decision. Uh, I'll say that. But uh, so I actually funny enough, I got into riding a bike in college in South Dakota. They changed the law. Uh, the dui chapter now says at the top of the chapter, you can no this chapter no longer applies to foot pedal or animal conveyance. So you can't get a DUI in South Dakota on a bicycle, and you can't get a DUI in South Dakota on a horse anymore. Uh, so I was in college in a small town, and I thought, what the hell? The bars are two miles away. It's a bit of a long walk. I can get on a bike and be there in five, 10 minutes, and I can ride back up to the dorms. And that's kind of what really I mean, I loved riding a bike as a kid and stuff, but that's what got me into these longer rides. One of my friends was like, You can't ride all the way to the next town over. The next town over was like 13 miles, so I just did it on the lunch break. And I kind of been into bikes on a little more of a casual level ever since. And uh a couple years back, I trained up to ride ragbri. There's a big ride across Iowa. There's 20 or 30,000 people that do this ride. It's a big, crazy, it was an incredible experience. But as I'm going across Iowa, I'm stopping in these towns and I'm looking at these venues. I'm like, I've done a show in that venue. And later that same day, I've done a show in this venue and the next day and the next day. And I kept seeing these, and I'm like, there's no reason why I can't like I could have I could have been doing shows this whole week riding across Iowa. So I just decided to throw it together. I was like, let's go for it. Um, so I did one last year, I did one this year as well. Uh last year I stayed, I went north and south across South Dakota, um, stayed on the east end of the state. This year I I left my front door in Sioux Falls and I rode all the way out to uh Rapid City. So I did uh Pier and uh Mitchell and Pier and Hill City and Rapid City, uh Alliance, Nebraska, and Garing, Nebraska, all on this big I did it. It was a another thousand-mile uh bike tour, and uh I did over I climbed more than Mount Everest. Like it was a crazy, incredible experience, but it is absolutely insane to look at comedy and go, you know what? This needs is more travel time. Yeah, I don't spend enough time on the road, I need to do more of that.

SPEAKER_01 19:47

Yeah, but yeah, I I need to get as sweaty as possible on my way to the show, yeah, and then take a shower in a crappy campground shower house.

SPEAKER_00 19:58

If you're lucky, there's there's a couple of shows I poked a hole in the top of a water bottle and soaped up behind a camper cabin to get cleaned up before doing the show.

SPEAKER_01 20:11

Oh, yeah, that's like an old school survivor man trick where you feel the water bottle and then you hang it from a tree branch or something. Yeah, yeah.

SPEAKER_00 20:20

I just I just did her squeeze style, and yeah, I wish I I wish I could say I've never had to do that when traveling to a show in a car, but I have so yeah.

SPEAKER_01 20:34

And that's the dedication.

SPEAKER_00 20:36

Yeah, there's been a few, just like travel falls through, there's not a truck stop nearby enough to catch a uh shower at the truck stop, the hotel's another 40 miles away after the show, whatever it might be. I've uh you end up getting yourself into some weird situations being out on the road like this.

SPEAKER_01 20:56

Yeah, I mean, along on one of those bike rides, did it ever cross your mind? I mean, I it's it had to, where you're like, shit, I don't think I don't think I'm gonna be able to make this.

SPEAKER_00 21:06

Yeah. Um, that actually this year, the first ride uh out to Mitchell, there was a storm that was supposed to come through in the afternoon, and the weather was supposed to be kind of clear up until it came through, and then the storm actually moved in earlier. And by the time I woke up, the storm was already like happening in town. So I decided to kind of wait it out. Well, on the back end of the storm, there was like 20 to 30 mile an hour headwinds, and so I was fighting headwinds like that for 75 miles all the way out to Mitchell. And I actually walked into the theater, leaned my bike against the wall, grabbed a Dr. Pepper, went in the green room, put on my jeans, and went on stage to introduce because I did a little intro of the show. I didn't have to do my set right up front, but I did a little intro for the show, brought up the feature act, and then I got to Go back and relax for a little bit, but that's uh that was one I did off a full bike ride without the shower. So if you bought Mitchell, thank you so much for dealing with my smell by the merch table.

SPEAKER_01 22:15

Yeah, you got a t-shirt and some body odor. Yep.

SPEAKER_00 22:20

Little koozie with some funk on it.

SPEAKER_01 22:23

Yeah, yeah. Did you I'm uh whenever I'm in a situation like that where it might have been a little bit stressful getting into the gig, oftentimes I'll find that that winds up being one of my best sets. Is it do you experience something similar to that when you go through stress to get to the show and then you get up there, you make it? It's like all that relief, it just like you just it just something brings out the best in you.

SPEAKER_00 22:49

Yeah, it's uh uh I feel like when I was opening shows, it was a little bit more of a mixed bag. Um, because then you go up and you still have that nervous energy, and maybe like sometimes that that can help a little bit, but maybe it takes a little while for you to break into the crowd. Like sometimes the crowds aren't really ready to go right from the the rip, you got to kind of get them used to loosened up and used to laughing and stuff, and then those shows, it just kind of puts you in even more of a frantic mind state for the the rest of the night. But but then that show in Mitchell was actually a really incredible show. So I uh a lot of times if I have just enough time to kind of sit down, if I have like five to ten minutes at least, if I can sit down, calm down, have a drink, and then get back up there and get after it. They it it does do something to you. I there's something about a survival mindset being in that fight or flight. You can hop right back into the show, and uh you kind of feel like you're you're fighting for your life when you're you're trying to make them laugh. And if you don't, you really will die, not just in the uh figurative sense.

SPEAKER_01 23:59

Yeah, you really will die. Yeah, yeah, I like that. I like that. Skylar Books, he's on the cover of the latest edition of America's Best Bar Comics, Volume 2. Volume three is going to be coming out this fall. Uh, I wanted to put you on the cover. You've been so dedicated going across the country. I mean, obviously you're dedicated. You get on a bicycle and you will ride hundreds of miles just to get to the gig. I absolutely love that, dude. I think that is so cool. What would you say, in your experience, makes performing in a neighborhood bar different, other than the extra drinking? What would you say is diff the biggest difference between performing in the neighborhood restaurant, tavern, neighborhood bar as opposed to a traditional sanctioned comedy club?

SPEAKER_00 24:47

I feel like well, so a lot of comedy clubs are in bigger cities generally, and a lot of times in bigger cities, there's a there's a an amount of pandering that goes on uh from a lot of times from the comedians, especially from the comedians that live in that city, you kind of know what people believe and expect, like politically or whatever, and and so it's a lot of like local references, or you're you're really pandering to the the bigger crowd or whatever. And that that's not always gonna fly in the small town because even in a small town, no matter what you think of what their politics or religion or whatever might be, you can definitely be wrong. I've been in places that you would think would be the most conservative place in the world, and it's actually surprisingly liberal, and vice versa. And so you just have to kind of just stick to being funny. You can't kind of play that that edge where you're trying to like it's the clapped or is what I've heard it called, yeah. So, you know, you tell people what you believe, and then they they have to clap for you, and that that that kind of breaks you into the show. And I don't like any of that. I'm just gonna start out by being as funny as possible. I'm gonna start out with some silly one-liners so that we can have some fun. Uh, and I I don't do anything that much different. Um, in a bigger comedy club, I might just really rip, like just start hitting the punch lines and cut out as much fat as possible. In the smaller towns, I kind of want it to be a little more conversational, where I kind of I want them to get to know me a little bit and I want to get to know them a little bit to make it a little more of a personal show.

SPEAKER_01 26:37

Yeah, you make a better connection, you make it more conversational because they all know each other in those small town bars and big city comedy clubs, it's gonna be more of a mixed bag of strangers, and yeah, that that's a smart strategy where just make the connection with because when you're in the small town bar, you're in their clubhouse, and so yeah, if you want to get up there and deliver like a one-in-show monologue, they will tune out. You got to bring them in and and make it like a conversation, like you just said. That's great, yeah.

SPEAKER_00 27:09

And and the fact that they all know each other, they're a little more likely to kind of jump in and rib you back a little bit, and so you gotta be ready, you gotta be ready to fire back off with those kind of things, and I think that's a little bit of fun, uh honestly, especially starting working shows with you guys in uh like Wisconsin was notorious for that.

SPEAKER_01 27:30

That's right, and and you know you're hitting, you know, you're being relatable, especially in those small town bars, they all know each other, and you could be talking about something that's just you know, uh, just some basic everyday life stuff that might frustrate you, but everybody in that town will know the story of Fred, who'd had a similar situation, they'll all start pointing at him, and you're like, Whoa, what the hell? And uh, so then you gotta kind of play with that because if you just roll over and ignore it, they'll they're gonna they're gonna feel ignored, and then they tune out.

SPEAKER_00 28:06

Yep, yeah, they want to be seen.

SPEAKER_01 28:09

They want to be seen. Well, I love it, man. Thanks for taking the time to do this. Go to Skylarbolks.com, check out his website, go to barcomic ticks.com. You can see where Skylar's gonna be headlining the pub and grub comedy tour coming up soon. And what about your social media? Anything you want them to check out there with jokes and spokes or anything else?

SPEAKER_00 28:30

Um, yeah, you can search jokes and spokes. Uh, all my social media is at Skylar Bolks, S-K Y-L-E-R, don't spell it A-R. I've got a lifelong feud with a Skylar who stole my name from my mom and mom's class. So that's a whole nother story. Go to my social media, maybe I'll tell that story someday uh on there. But everything's at Skylar Bolks.

SPEAKER_01 28:54

All right, and if you want to uh check out uh Skylar's page in America's best bar comics, you can grab that off of Amazon. I appreciate it, buddy. Thanks for doing this today.

SPEAKER_00 29:05

Thanks so much for having me, man.

SPEAKER_01 29:07

Yeah, let's hear it for Skylar, everybody. Virtual round of applause. All right, buddy. We'll see you soon down the line.

SPEAKER_00 29:15

Right on. Thanks, man. Have a good one.