While touring the nation as a standup comedian does have its perks – the occasional attractive groupie, the venue picking up your bar tab, and the ego boost of a live audience fawning over your every word, it’s not always a bed of roses. Just ask Adam Carolla. The comedian/former Man Show host has seen the not-so-shiny side of taking a comedy show out on the road. And after reflecting on some of his crazier experiences, he was inspired to write his latest cinematic endeavor, Road Hard. The film, available on Blu-ray and DVD on October 6th, follows Bruce, aka Carolla, on a fictional journey through trying to pay for his daughter’s college tuition via a reinvented standup comedy career. “There was some artistic license but a lot of stuff that was based on things that actually happened,” says Carolla, of the plotline.

Playboy caught up with the famed TV/radio host to discuss his worst comedy blunders, his one survival tip for aspiring standups, and why he’d rather hop off a bridge than reboot any of his past projects like The Man Show or Loveline.

Tell us about the inspiration behind Road Hard and why you decided to write it.
It’s been a while since I’ve done a movie. I had this platform with this podcast and I thought, maybe I can crowdfund this movie. I just started ruminating on what kind of movie I wanted to write. Usually the stuff I do is personal and I just thought, “Let’s talk about in a way what I had to go through over the last few years when the economy got bad and I lost my radio show job and I just went back out there on the road.”

In your real life experience, what is one of the toughest rooms that you ever performed standup for?
I went and played a college that was in Mansfield, Pennsylvania and it was just a preshow for a bunch of 19 year olds that didn’t care. There was probably 50 people that showed up in an auditorium that held 300 people. It was snowing outside and there was a cold Dominos pizza waiting for us when we got there. We were staying in Mansfield, Pennsylvania in a cheap motel with a bunch of rough neck oil drillers and I just remember thinking, “Wow. This is what it’s come to, huh?” I don’t feel sorry for myself too often but I actually felt sorry for myself. I was like, “Man. You just bottomed out!. Geez. Look at you.” I remember it was very humbling. I just remember thinking, “You had some pretty good success in this business and this is what it’s come to?” That’s probably about the low point for me.

You made your directorial debut with this film. How does Adam Carolla direct Adam Carolla?
I did another movie called The Hammer and we had a director but I ended up doing a lot of directing of myself. I feel like when you make this kind of movie and you’re in every scene, you end up just sort of directing yourself anyway because you’re in charge of your own acting and reacting. And as it pertains to the other people in the film, I wrote all the parts for them so I knew what I wanted them to do. I just sort of thought, “Let’s cut out the middle man.” Me and my writing partner, Kevin Hench, wrote it and we figured we might as well direct it since we’re more familiar with the material than any director would be. I would sit in the scene and I would have Kevin sitting in video village and I would do the scene and yell, “What do you think? Did we get it?” and he would yell, “No. Do it again” and that was about as much of the process as there was. Everyone turns it into some high salute and some ethereal artist endeavor but a lot of it is mechanical. The director of photography is the one who more often than not says, “Let’s do it again because we didn’t get the camera movement in the way that we wanted it. We didn’t get the lighting in the way we wanted it. When you lifted your hand up, you made a shadow across your face, turn this way.” It’s really a lot less artistic than people think.

You crowdfunded this film. Did you have to give fans that made donations any crazy gifts in return?
I was just in England doing a show and had dinner with a fan that lives in England after the show that was one of the donors. I did standup in somebody’s living room. There is fair bit of that. I’m not one of those people that looks at going out to lunch with a fan as a major inconvenience. As a matter of fact, I know a lot of people say this, but my fans tend to be very educated, fairy affluent, and super articulate. I end up going out to lunch with these guys and it’s just as interesting to me as I’d imagine it is to them. I learn a lot. These guys are not roofers. They are very interesting people and are smart and have a lot to share. I have a good time with them. So it’s like, “You’re telling me I gotta go to lunch with a bunch of people that really interested in what I have to say? Doesn’t sound like a chore for me.” You’re going to lunch anyway. You might as well do it with someone that worships you, right?

Your character gets approached a lot for being on a former show called Bro Code. You must be recognized a lot for things that you’ve done like Loveline and The Man Show. What’s the strangest fan encounter that you’ve ever had?
There is always the drunken person after the late show that is screaming, “It’s my birthday.” You don’t understand. You take a picture with them and then they scream again, “It’s my birthday” and you don’t understand. You take another picture with them and they are like, “Let’s take another picture” because it’s their birthday. There’s always the drunken fans. But honestly I have a high tolerance for that stuff. I’m not skittish or easily freaked out. You can put your hands on me and I don’t care. I’m actually sort of tailor made for drunken fans because I spent the whole early part of my life just wrestling with drunken friends. I’m fine with it. But I do have really good smart, just the best demographic you could ever want.

Is there one question that you get asked the most by your fans?
They do a “Bring back The Man Show! Bring back Loveline!” Sometimes “Bring back Crank Yankers.” There’s a lot of “bring back.” And that’s not how I’m wired. I’m not in the bring back mode. It just doesn’t make sense to me. To many, if you’ve got nothing to say or nothing to do, then you get the bring back mode. But I’m in what’s next mode, not bring back mode. That’s how I think everyone should be creatively. I don’t get how Sid and Marty Krofft sit around all day and try to figure out, which piece of shit TV show from the 70’s they can dust off and make into a movie today and then we end up with Land of the Lost The Movie. And it’s like, I’ll kill myself if 20 years from now, I’m trying to get Man Show The Movie made. It doesn’t make sense to me. It means you’re out of ideas, I’m guessing.

What’s one survival tip that you have for comedians who are headed out for a lengthy standup tour?
A lot of comedians may not be big smokers but when you’re done doing two shows and you’ve been drinking and you get back to your room at 1AM, you do want a cigarette. Most comedians smoke weed and the hotel room windows don’t open. So I was given a tip by my colleagues for those who want to smoke a cigarette in their bathroom or smoke a little weed when they come home after a good night of drinking or doing comedy. I’ve never done this but the tip apparently is you check into your room, you call down to the desk and you go, “Yeah just so you know, I did detect some smoke. It feels like someone was smoking in this room.” Then you proceed to smoke and later on if you get busted, you go, “Well remember when I checked in, I said I could smell some smoke?” Sweet right? Super considerate!

What was your first exposure to Playboy?
I used to babysit a couple of houses down for two kids and their dad had a Playboy. My dad didn’t have a Playboy but their dad had a Playboy. And I used to look forward to babysitting those kids because I used to stare at that Playboy every time I went over there. I knew right where it was. It was under the bathroom sink. As best I could tell, he had one or two; there was not a bevy of it. My friend in high school had a subscription to Playboy, I mean starting at age like 14. So he was a hero and we would go to his apartment and he had stacks and stacks of Playboys. It was a huge deal for us!

What movie scared you the most as a child?
Well it’s going to sound weird because it’s not really a horror movie, I just saw it when I was seven in the movie theater. It stars Dustin Hoffman and Steve McQueen and it’s called Papillon. And it’s a good movie and I recommend it but it will haunt you if you are young. It’s about a prisoner who escapes from Devil’s Island in French Guiana. It’s based on a true story. It’s a really good movie, anyway.

If you were on Death Row, what would you last meal be?
If they are going to put me to death, it wouldn’t be in California. I mean they have a Death Row but they don’t put you to death. So they would do it if I was in Texas. And so I guess I would have to be in Texas in which case I would ask for an In-N-Out Burger because I don’t think they have In-N-Out in Texas. Then they’d have to go to California to get it. I’d probably buy myself an extra 72 hours or something. And then when it got to me, I would complain that it was cold and I would send it back.

What was your first car?
My first car was a truck, which was a Mazda pickup truck from like 1977, which I had to drive because I was a laborer. I rode a motorcycle and my boss told me if I bought a pickup truck, he’d pay me another $1 per hours, so I bought the pickup truck.

What is your pop culture blind spot?
I would say just about any music after Steely Dan broke up. Probably any music of the last 10 years. I sit around and I see that Wiz Khalifa and Tyga and Iggy Azalea and all that are mega stars and I can’t figure out why they are mega stars. I have no idea what they are up to that is making them the money that they are making. I’m sure they are doing it honestly; I’m just completely out of touch.

What’s the first song that you knew all the words to?
I have to say “Happy Birthday” because that’s probably the first one that you join in on. I mean the words change depending what your name is but I’d sing “Dear Adam, Happy Birthday to you.” I probably learned that at three. And then after that, “Hell is for Children” by Pat Benatar.

What’s the biggest lie that you ever told?
I said I was in Chinook helicopter that was shot at over Iraq and it really wasn’t. It turned out we landed quite safely. There was that lie. There was another one about the time that I was in the second tower of the World Trade Center when the plane hit the first tower, that didn’t go so well. And then there was the lie that I just kind of got busted on about me and Caitlyn Jenner dating. That one was pretty embarrassing. Those three are probably my top three.