Hey guys! I've been on reddit for four years. I've been doing stand up for two and a half. Here's a video where I get incredibly sweaty while telling jokes. : http://www.youtube.com/watch?v=SsCRv_8Qvu4

I'm still very new in terms of comedy years. I've been lucky enough to open for Harland Williams, Sam Tripoli, and Tony Hinchcliffe. I also recently got to perform on a showcase at a festival with Kyle Kinane.

I also tour with a group of four other comics called Race to the Coffin Comedy. You can find that at www.Facebook.com/RaceToTheCoffin

Also just for fun here are a couple of my standupshots from /r/standupshots:





Will post a confirmation on my Twitter at www.Twitter.com/timrosscomedy

Ask Away!

Comments: 154 • Responses: 62  • Date: 

Rontastic27 karma

You're probably one of the funniest dudes I've seen in /r/standupshots. You're also a pretty solid guy (no pun intended) on Twitter also.

What are the three biggest things you've learned about stand up in the time you've been doing it?

TimIsWin31 karma

Thank you! The three things:

1) Failure isn't the end of the world. It's necessary and it is a tool to get better.

2) Comedy is hard.

3) Girls are nicer to ugly guys if they make a room full of people laugh for a little while.

w0rdean21 karma

I take partial credit for this AMA.

TimIsWin14 karma

You should haha

slartibartifart16 karma


TimIsWin75 karma

I'm working on a screenplay about a man with an incredibly small penis. My title is taken though. I was gonna call it "He's just not that into you"

davidhboyd15 karma

What is your go-to response to a heckler?

TimIsWin23 karma

I don't have a go to response. I'm kind of silly on stage so I can't be brutal to a heckler and then hop back into silliness. I usually just playfully make fun of them until they feel dumb and shut up. Sometimes they get mad. One time I shut a girl up and then later in the set called her out on the fact that she was texting each of her friends about what an asshole I was. She hated me but her friends laughed really hard haha.

A-Lo_in_the_B-Lo11 karma

To what degree is that photo you use an accurate representation of the current state of your beard?

TimIsWin13 karma

Not at all! My beard is much bigger now. I will try to find a more current picture.

stevebeyten11 karma

Do you believe women should be proud of their butts?

TimIsWin26 karma

Girls be proud of ur butts

frakkinadama8 karma

Tim, you are THE reason I subbed /r/standupshots and let me first say thank you for being awesome and funny hilarious. You wake my work days a lot more enjoyable.

As for the question:

Stand up comedy has always been something my sister /u/karafrakinthrace and I have talked about doing together but we really don't know where to start, do you have any suggestions? Local clubs? Bars? Or should we try the online community? Where did you get your start in comedy?


TimIsWin6 karma

You gotta do open mics! The only way to get better at stand up is to actually do it. If you live in a city check out badslava.com. if not search Google for open mics near you and go do some. Open mics are crucial.

frakkinadama6 karma

Thanks for the tip and the link! We will definently look in to doing some open mics and see where it takes us!

TimIsWin7 karma

Let me know how it goes!

ngumu7 karma

I'm black and I read but I don't have a British accent. Does two out of three count?

TimIsWin7 karma


SilentMarauder7 karma

Come back to the GroupMe, Tim. We out here now

TimIsWin9 karma

Miss u guys

Gravy-Leg__7 karma

Can you tell us the story of the time you bombed hardest?

TimIsWin11 karma

I tried to do a set of new material that I wasn't comfortable with or confident in. About three minutes into a five minute set I clenched up and said "that's all. I'm done" And just walked away. Also recently I ate it for twenty full minutes in a southern themed bar. That was frustrating. I was throwing my hardest pitches and just coming up empty.

YellowElevator5 karma

Has there been, or do you think there is anything else in your life that you've worked as hard at as comedy?

Do you have short-term, specific goals that you actively work towards or do you just take things as they come? What are they?

What has been the most valuable advice that you've received re: your comedy career and who was it from?

TimIsWin7 karma

Nope. I've done lots of things. I was in a band, I did slam poetry, I did plays. But I've always gotten bored with other things. And I'm also not good at anything really. I was terrible at focusing in school. I dropped out of high school and then left after two years of community college.

Short term goals: Getting booked more frequently, writing new jokes, getting better at certain things on stage. (Inflection, crowd work, storytelling. I'm an awful storyteller because I want to rush to the jokes.)

I ate shit really hard at an open Mic one time. My buddy TJ Amick was hosting and he told me "if you can count the number of times you've been on stage, you don't need to worry about doing poorly." It's absolutely true. Once you can no longer count you still do poorly sometimes but it doesn't hurt as much as it did when you started. Also my buddy Aaron Kleiber has given me tons of practical advice about being on stage. Check him out at www.Twitter.com/aaronkleiber. He's hilarious and has opened for Bob Saget and Sinbad and Bert Kreischer and a ton of other headliners.

pher14925 karma

Why'd it get so cold!

TimIsWin7 karma

It usually gets pretty cold in the winter.

pher14923 karma

But it was warm an hour ago

TimIsWin5 karma

I think you're going through menopause

jordanlasso4 karma

Hey Tim! Just listened to your stand-up! you're on the front page. Congrats. Hopefully it gets you some good views, but I have a question for you, why do all your bully guy voices sounds really mexican? Like if you would've added an "ESSSSSSSSAAAAAAAAYYYYYYYY" it would've been super mexican I thought it was hilarious, I was just wondering.

TimIsWin5 karma

I have no idea! Hahaha

CarPeriscope4 karma

if you were a hot dog and you were starving, would you eat yourself?

TimIsWin8 karma

Without a thought

quillyy4 karma

Have you ever masturbated to the Sims?

TimIsWin7 karma

Hahahahaha is this Naf ILU


What's the most played song on your iPod right now?

TimIsWin14 karma

Kendrick Lamar's entire Good Kid Maad City Album.

mostlynein3 karma

Any favourite comedy movie?

TimIsWin7 karma

Dumb and Dumber, Tommy Boy, Rushmore.

DieKnowSoar3 karma

I've been a redditor for only a few months. Are you better than me?

TimIsWin5 karma

No I've just traded away more of my social life

Gravy-Leg__3 karma

How do you come up with your material?

TimIsWin5 karma

A lot of it is just bullshitting with friends. If I say something that could work out on stage I take a note on my phone. I also like to pick a topic and just see how much I can mine from it. I have a bit about barbershops that came from that.

yarissey3 karma

what made you think that using /r/standupshots was a viable promotional tool?

TimIsWin4 karma

I think you're being sarcastic but I can't tell haha. Either way - I was already on reddit all the time before the subreddit was created so it just seemed natural. I like that I can share a joke with a few thousand people whenever. And it's gained me a bunch of Twitter followers, some of which are really cool and interact with me on there. So in that aspect it's totally worth it and a great way to connect with people I wouldn't have known otherwise!

CunthSlayer3 karma

Who is your biggest comedic inspiration and why is it ODB?

TimIsWin8 karma

Because Wu Tang is for the children.

Also Brian Regan and Mitch Hedberg were my two absolute favorites.

yomammary3 karma


TimIsWin6 karma

Hi French Canada

yourfriendjeffrey3 karma

Dude, 2 things. 1. You're hilarious 2. I hold your gaining momentum as the reason for the decline of the hxcboards.

TimIsWin1 karma


yourfriendjeffrey2 karma

No faceeater, also I supported the race tour. You should come to Louisiana man.

TimIsWin1 karma

Awesome did you get your shirt and stuff? They were sent out recently

yourfriendjeffrey1 karma

Haha yeah I got it, I'm sure I bothered the hell out of the dude that sent them because I msged him twice on Facebook asking what was up. But seriously dude New Orleans is great to comics.

TimIsWin1 karma

Word up man

Temporarily__Alone3 karma

I love your standup shots.

How does it feel to post an AMA just minutes after Trent Reznor?

TimIsWin5 karma

I feel Temporarily_Alone

greensign3 karma

What got you into comedy?

TimIsWin7 karma

I've always been interested in being funny and performing in general. I was in plays constantly and wrote sketches for my schools morning announcements. When I discovered Mitch Hedberg and Brian Regan I realized what I wanted to do. But it wasn't until I took a public speaking class at community college that I really decided to go pursue it.

bstraw143 karma

Who's you're favorite comedian?

TimIsWin8 karma

Louis CK

River_Guard3 karma

Who is the one comedian still alive today that you'd most like to perform with? (Sexually, or in a comedy show, although I imagine that both will have an element of sexuality/comedy regardless.)

TimIsWin4 karma

Either Louis CK Bill Burr Chris Rock or Kevin Hart. Or Todd Barry. Or John Mulaney. Or Tig Notaro. There are so many great working comedians right now.

AubreyPlazasButtHair3 karma

Who is your favorite female comedian?

TimIsWin7 karma

Tig Notaro! She is so fucking talented. Her first album is hysterical. And Live is the only comedy album to ever make me tear up and laugh at the exact same line. Maria Bamford is great. Sarah Silverman, Amy Schumer, Jen Kirkman, Chelsea Peretti. "Woman aren't funny" is a myth.

YellowElevator3 karma

I think we all know what answer you're hoping for.

AubreyPlazasButtHair3 karma

Yea I love Iliza Shlesinger

TimIsWin4 karma

Forgot about Iliza she's great

DanOlympia2 karma

Oh yeah, second question. What are your favorite podcasts?

TimIsWin2 karma

Didn't you tell me about WTF? My Inbox is so confusing right now Dan

DanOlympia2 karma

Could be. Lately I've been listening to Stop Podcasting Yourself (silly Canadians!) and Caustic Soda (Info-tainment!). I really like Pete Holmes' show too.

P.S. What does e-validation feel like? Is it anything like the proud nod of a father? Or your first lover's warm embrace?

TimIsWin2 karma

It's pretty sweet holy shit my Twitter is going crazy it's awesome

miles9202 karma

Do you have any more vids? You're hilarious and it would be great to see more content!

EighthHorcrux2 karma


TimIsWin1 karma

Gotta do it enough times in front of enough crowds!

GJENZY2 karma

The first thing I thought when I saw you in that video was "that guy looks like he likes beer". And then you started drinking from a can on stage. Was it beer?

TimIsWin2 karma

Sure was I love beer!

DanOlympia2 karma

I have a secret goal in my head of performing at my first open mic before the end of the year. I'm funny casually in conversation but it's hard to be funny on purpose when people are expecting to be entertained. Any advice?

TimIsWin3 karma

Dan I know you and you're hilarious just go do it.

TheSporkening2 karma

Tim, talk about your technique. I imagine the process being like this:

  1. Write bits in your head.
  2. Commit to paper/computer
  3. Try out on friends who have been honest
  4. Perform

Would that be accurate?

As an aside, I have only seen you in the imagur image/text stills like the ones you posted. I want to see more. I am going to be so bold as to suggest that you let me know when I can see you perform on TV.

"Masturbate Furiously" is the answer you should give to every question you do not have a legit answer to. Just sayin'.

TimIsWin3 karma

Technique is generally one of two things. Either I say something funny and write it down and come back later or I pick a topic. If it's the topic thing I will write that in a big bubble in the middle of a piece of paper and branch off a bunch of things relating to that.

Then regardless of the previous method I stand on my porch or sit in my car and just talk to myself about those things until I can start to form punchlines and trim away unnecessary words and sentences. Then I try it out at an open Mic or run it past a couple of comic friends that I bounce ideas off of.

Sometimes it just comes from riffing on stage and going off on a tangent or doing a bit of crowd work or something. Those bits are usually the most fun.

TheSporkening3 karma

You=the man. Keep on keep in' on.

TimIsWin2 karma

Thank you! Appreciate it man.

catsfive1 karma

I have seen this bubble thing of yours in "creativity" software (like mind maps, etc.). I wonder if the software would work for a comic.

TimIsWin2 karma

I'd imagine so. The mind map thing is basically what I do


What are some of your favorite subreddit(s) outside of the default ones? Congrats on the 4 year reddit anniversary!

TimIsWin2 karma

Your subreddit because I love tits a lot. /r/hiphopheads /r/mildlyinteresting /r/cringepics (I know it's mean but it makes me chuckle) /r/nfl


I love tits too! Thanks for the reply. My personal favorite are /r/ExpectationVsReality (I think you'd like this one), /r/CabinPorn, and /r/StuffOnCats

TimIsWin2 karma

Those are neat. I'm allergic to cats though so that is pretty upsetting

scalp_em212 karma

who would you say are some of your influences?

TimIsWin3 karma

Hedberg, Regan, Birbiglia, Louis, Mulaney, Buress.

RicsFlair2 karma

What was the funniest standup bit you ever heard in your entire life? And if possible, please link us it to youtube. BTW, I love your stuff in /r/standupshots.

TimIsWin3 karma

Way too hard to say!

johnnynoname122 karma

Does your clique of comic friends hate all the "alt comics"? also is david sedaris funny? I'm not a WASP so I was hoping someone can explain this to me

TimIsWin2 karma

Pittsburgh is a small scene so we don't clique up as much in that way. I hang out with all kinds of different comics. The guys I tour with would probably be considered "alt" by some people. I dunno. I just like funny.

I like reading David Sedaris.

racetothecoffin2 karma

i want to participate. how has john dick winters influenced your comedy? and you life?

TimIsWin2 karma

He's made me hate myself more so I assume that's made me funnier.

racetothecoffin2 karma

don't blame your self loathing on other people you hairy beached whale of failure.

TimIsWin2 karma

I love you

fscvatommygundacreep2 karma

Who's your favorite rapper and what's your favorite hip hop song?

TimIsWin2 karma

Too hard to answer. Right now I'm listening to a lot of Chance the Rapper and Kevin Gates

grobota2 karma

You mentioned being a fan of Tig. Just wondering if you've ever listened to her podcast, Professor Blastoff?

As a sidenote, I think you'd be an excellent guest on the show.

TimIsWin2 karma

I need to check it out. I love her! She's so quick witted

rhinojazz2 karma

I just watched your video and found this AMA. You're pretty funny. Do you have a website or anything? Do you have like a CD or anything we could buy to show our support?

TimIsWin1 karma

I don't yet! Best support is to tell your friends!

w0rdean2 karma

What got you into comedy? Do you plan on touring more?

TimIsWin2 karma

I've always been into comedy. As a child my grandmother used to get me gift certificates to bookstores. Every year I bought at least two joke books and read them cover to cover. In middle school I said I wanted to grow up to be Chris Farley (before he died). It's just something I've always loved.

Yeah! Hopefully Race to the Coffin gets back out on the road sometime soon.

w0rdean2 karma

I mean, not that I want you guys to leave town, it's just that I can tell people I know in other cities to see you. Although, Alex does scare me...

TimIsWin2 karma

One night Alex and I got very drunk and sat around watching British comedy and swigging from a bottle of whiskey. He's pretty harmless.

w0rdean2 karma

Scares me in a good way. He fucking killed at the Arcade theatre show. A uniquely disturbed set of material and delivery style.

TimIsWin1 karma

Yeah he's awesome. Just don't tell him that Monopoly sucks or he'll flip out he fucking loves Monopoly.

w0rdean2 karma

Drug of choice? Will there be another kickstarter? Can I get drunk with you guys some night?

TimIsWin3 karma

Alcohol! Weed sometimes. I also take Xanax but not for fun. I doubt we will do another kickstarter but possibly. Yeah man we get drunk pretty often. I plan to be drunk after the Dec 20th show.

jakkes121 karma

Why did you start doing comedy? Where and how did you start?

TimIsWin1 karma

I did a public speaking class and made all of my speeches funny. I loved the laughs and decided to try stand up. I started at an open Mic at a place called The Smiling Moose in Pittsburgh

thejshep1 karma

I have a friend who is single handily building the comedy scene in out city of 100k (booking the venues to hold the shows, booking the acts, doing stand-up himself etc.) What advice would you have for someone taking on such a massive task? Thanks in advance!

TimIsWin2 karma

Get other people involved! There need to be other comics setting up weekly open mics. That's the foundation of a comedy scene because it's where comics meet other comics and get good. He should teach them how to work a deal with a bar on an off night to bring in an open Mic. Most bar owners who have a slow night will pay the host a small sum of money to host a Mic that brings people in who wouldn't be there otherwise.

HansChuzzman1 karma

How long have you been doing stand up for? How long after you started did you get your first paying gig ?

TimIsWin2 karma

2 and a half years! First paid gig prolly five months in.

RhynoSorceress1 karma

Hey man your pretty damn funny. At the start of the video they say your from Pittsburgh. Do you know the comic Davon Magwood? He radomly started following me on twitter and I think he's pretty funny. Shitty question I know but was the only thing I could think of that hasn't already been asked. Wish I had the balls to get on stage and try stand up, keep it up man, your time will come!

TimIsWin1 karma

Appreciate it, man! I know Davon.

saatzer851 karma

Should Paul walker have slowed down?

TimIsWin1 karma

He wasn't driving but he should have told the driver to slow down cuz I like fast and furious movies

skimfreak921 karma

What do you say to the fact that www.redditcakeday.com says your cakeday is dec. 4th and not Dec. 5th?

TimIsWin2 karma

Apparently the cake was still showing up this morning! I'm a dummy