Welcome To Kaboom!

Join Today!

New Music

Crazy 8’s w/Comedian Will Miles

Crazy 8’s w/Comedian Will Miles

At the end of every day, Kaboom! Magazine trends to get a little crazy. So what we like to do is have some fun with one of our favorite celebrities, models, recording artists, or social media personalities by asking them eight of the craziest questions we can think of in our funniest feature entitled “Crazy 8”s.” Today, we get a little crazy with Chicago, IL comedian/writer Will Miles as he tells us all about how he has sex in his dreams, why Santa likes bad girls, licking a lightpole at 4am, and many more. Its only 8 questions, what can possibly go wrong?”….it’s Kaboom! Magazine…..so everything can go very wrong.

Will Miles Info:
Age: 33
Zodiac Sign: Gemini
Hometown: Chicago, IL
Occupation: Comedian/Writer/Actor
Instagram: @MrWillMiles
Twitter: @MrWillMiles
Facebook: facebook.com/WillMilesComedy
Snapchat: @mrwillmiles
Personal Website: willmilescomedy.com
If you could have one crazy night with one person (past or present) who it would have to be…..: I would want to go have a crazy night with Cheech and Chong at the height of their 1970’s success. I might want to bring some modern day weed but I’d try theirs first. But smoking with those guys all night has always been a dream.
Do crazy people exist: Yes. Most certainly. A lot of them are untreated and some even have really good jobs. Some run for president.
You know you’re crazy when….: You lick a subway pole at 10AM.
What is the craziest thing you’ve seen in the past 30 days: In LA, I saw a dude shit in the bushes on Sunset and then put a pile of clothes on top of it to cover it up. I saw that and still happily went to get Thai food a block away.


1. When was the last time you had sex in your dreams?
I have sex in my dreams at least once a week. I stay fuckin.

2. Why does Bugs Bunny walk around the cartoon naked, but he puts a bathing suit on when he goes swimming?
If there’s one thing I know about rabbit genitals, its that you don’t want to get those wet. I also know zero things about rabbit genitals.

3. If a homeschooling mom is talking to herself, is she crazy or is it a parent-teacher conference?
What’s weird is that when that woman masturbates, she is fucking her kids teacher. I would say it’s a parent teacher conference, but most certainly also crazy.

4. Is the reason Santa so jolly because he knows where all the bad girls live?
Santa is so jolly because he has all that access to North Pole weed, and i heard that shit is fire. That’s why he always wants cookies. And it’s creepy to go after women because you know where they live. When you got North Pole weed, they come to you.


5. Does killing time damage eternity?
nah. killing time is the reason there is an eternity. it’s like they say, you gotta kill time to have time.

6. Would you rather have the best house in a shitty neighborhood or the worst house in a fancy neighborhood?
By far I’d rather have the worst house in a fancy neighborhood, because then you know you are about to get a sick ass offer on that house so they can tear yours down and build a condo. With that money, you buy a new doper house in a neighborhood right in between fancy and shitty.

7. Have you ever dated two girls at the same time?
most certainly. a number of times throughout my 20s. But they kind of knew about each other. there were a lot of “don’t ask, don’t tell” situations going on. I didn’t care who they hooked up with, they didnt care who i hooked up with. i think your 20s are supposed to be a little wild. i didnt use the term “girlfriend” for real until my 30s when I actually meant it.

8. Why is a carrot more orange than an orange?
Thats just our eyes playing tricks on us, yo!! and carrots are good for the eyes, so they like fuckin with them all the time.

*Will Miles a Comedy Central “Comic To Watch” and he has a showcase in the New York Comedy Festival on Wednesday, November 2. He’ll be headlining a show at Cityside Bar in Boston at 8:30 on November 14. Will is also the cohost of the “Hopefully We Dont Break Up” podcast on itunes and a cohost of Comedy At The Knitting Factory every Sunday in Brooklyn.

Instagram: @MrWillMiles
Twitter: @MrWillMiles
Facebook: facebook.com/WillMilesComedy
Snapchat: @mrwillmiles
Personal Website: willmilescomedy.com