Hey guys. I've been doing stand up for four years now and I thought it would be interesting to give people some perspective for what life is like for a comic who isn't a national headliner. I host and feature for headlining comics and obviously I don't make a ton of money. It's taken me a lot of fun places though. I've been to Michigan, Indiana, Florida, Georgia, Minnesota, North Dakota and a slew of other places with my comedy. I got to perform on the same stage as Kyle Kinane at a festival in Florida. I've gotten to open for Harland Williams and Artie Lange and Big Jay Oakerson and a few other noteable guys.

I'm a frequent poster on /r/standupshots and I put together an album of some of my shots for you guys to check out: http://imgur.com/a/KZNdR

I love the people on that sub. Some really funny comics and really supportive users. Great sub.

If you are on reddit every day you might recognize me in this video from 2013 that hit the front page of videos: https://www.youtube.com/watch?v=SsCRv_8Qvu4

I was also on Steve Hofstetter's show Laughs: https://www.youtube.com/watch?v=88sHjNITI0U

And I have some other stuff at www.youtube.com/timrosscomedy

At any rate, that's what it is. I'm an unknown comic who performs at a non-headlining level. I do a lot of shows in VFW's and VFD's and bars and punk venues and lots of weird places. I sometimes tour with a group of guys who set up DIY shows at www.facebook.com/racetothecoffin

So go ahead. Ask some questions about doing comedy as a mostly broke depressed fat guy with anxiety!

Verification on twitter and what not: https://twitter.com/TimRossComedy/status/592387692777885696

(Although I can't imagine anyone would want to pretend to be me)

Comments: 100 • Responses: 34  • Date: 

imsupercereal413 karma

I love seeing you on /r/standupshots

In your opinion what is the best joke you've come up with?

TimIsWin10 karma

Man I honestly have no clue. Some of my favorite jokes I've written are really niche jokes. I love coming up with something accesible that I feel good about and can make a wide range of people laugh but I really love having a connection with the people in the crowd who get a weird joke with a weird reference. I usually don't tell them often though. Or I reserve them for a place like standupshots where a few people can enjoy them and I don't have to endure the silence that comes from telling them.

I think my personal favorite joke to tell is one of my silliest. It's an impression of Lil Wayne: https://www.youtube.com/watch?v=p_SeHz2cr8Y

HiHoBigBootyHoes10 karma

Should girls be proud of their butts?

TimIsWin6 karma


DoinItDirty7 karma

What do you do to deal with dead crowds? I remember one of your videos you were killing it but the crowd was just awful and quiet.

TimIsWin8 karma

Heh yeah that video was quite a while ago and it honestly wasn't as bad as it seemed. It was just a bit of a sparse audience. It really depends honestly. A lot of times I will try to engage the crowd. I'll try to talk people and do a bit of crowd work and try to get them interested and engaged that way.

Or sometimes you'll move a joke around in the set. Try and get to a big punch quickly to try and get them on your side.

But sometimes nothing's working and you just do your act and try to think about ice cream or boobs or something pleasant that isn't what is happening right now in the room.

DoinItDirty3 karma

Ice cream and boobs. You deal with bad crowds like I dealt with church growing up. Good on ya Tim. Thanks for the AMA! Also, I have a friend from Pittsburgh who would love to see your act. Where can she catch you?

TimIsWin4 karma

This Wed I'm closing out a show at a place called Caliente. It's called Joking Off (my buddy www.twitter.com/johndickwinters runs it and thought of the name BEFORE MTV2 did). It's a free show and I think it starts at 8 pm. It's in Bloomfield! Next month I'm going out of town to Frederick MD and Harrisburg PA

DoinItDirty3 karma

I move to Carolina and you go right through my area. Blah. Thanks man. Keep up the good work.

TimIsWin2 karma

Boooooo move back

spence406 karma

What advice do you wish you had been given when you were just starting out?

TimIsWin9 karma

Thankfully I got some of the best advice at my second or third open mic. I had just eaten shit terribly on stage and I was lamenting that fact to the MC. He shrugged and asked me "How many times have you been on stage?"

"Uhh..just a couple"

"Look man. If you can still count the times you've been on stage, you don't have to worry about bombing."

And it kind of gave me relief. Knowing that it was a long process and that you had to grow and get better. To know that it was OK to fail a bunch when you're first starting. It was really encouraging. And now I'm past the point where I can count the times I've been on stage and he's write. I still eat shit sometimes but now I just shrug it off and try to figure out where and how it went wrong.

ohseven10984 karma

Hi Tim, I think you're funny, but I don't want to drive to the other side of Pittsburgh to see you. Do you have any gigs closer to Butler County any time soon?

TimIsWin3 karma

Hey that's totally not far from me at all. Why don't we set up a show your way? I'll get some guys and you tell people about it. PM me and we'll figure something out.

hashbrownash4 karma

What is the funniest joke you have ever heard?

TimIsWin13 karma

My friend Alex Stypula has a joke that he closes his sets with. He goes "Aside from doing comedy I also play in a really awesome band. We're called "how to build pipe bombs and take down the government.

Please google us."

I laugh every time I hear it. Check him out www.twitter.com/AlexStypula

WhoIsZac3 karma

Hey, Tim, I appreciate you doing this AMA. I've been doing open mics for almost two years, so you're a few steps ahead of me. Here are some questions (I apologize if some are terribly generic, but I'm genuinely interested):

  1. What made you start doing stand up? Were you the class clown, a long time comedy lover, a guy who just decided to give it a shot on a whim, a combination of some/all of the above, none of the above, etc?

  2. What's your writing process like? Do you work most of your ideas out on stage or do you work it out on paper first?

  3. How do you make open mics feel productive to you? The majority of the ones in my city (Denver) are your standard "nothing but comics who aren't paying attention" setup, so it's hard not to feel like I'm wasting my time going to them.

  4. I went through a pretty major breakup a couple months ago and it, combined with the aforementioned open mics, has killed all my desire to go out and do comedy at the moment. How do you push yourself to go out and put in the stage time that is needed, even when you just don't "feel" it?

  5. What's your "plan" for comedy? Do you plan to try to scratch out a living solely from stand up or do you think you'll combine it with something like writing for a show?

  6. What was it like moving up to host/feature? When did you know you were "ready" or did you kind of fall into it?

  7. How many sets do you average a week?

Again, I appreciate you doing this. I've enjoyed your tweets and standupshots for a long time, so it's cool to be able to pick your brain. I might have a few more questions later, depending on how much actions this AMA sees.

TimIsWin0 karma

Hey man, thank you for asking good questions!

  1. I had done a few open mics before I actually started but then I just let it kind of fall by the wayside. I really started after taking a public speaking class. I just made all of my speeches funny and it reminded me of a dream I'd let slip away. So I scheduled a date to go out and after that first open mic I was just in it.

  2. It honestly depends. I think a lot of the time I'll write three minutes on a subject and I'll go up at an open mic and try to fill the other two minutes with that subject. I think my strength is more in sitting down and writing. (Well actually I generally pace and talk to myself for a long time haha) So instead of relying on that I've been trying to push myself to get better at being improvisational on stage.

  3. Just saying the words into a microphone with people present gets you more comfortable on stage and better at being a comic. Those mics are super tough though, man. It's hard not to fall into a habit of trying to make the back of the room laugh when the only people in the room ARE the back of the room.

  4. Man, I dunno. You just have to. I've been feeling super depressed lately. Yesterday I had a particularly bad set and on my drive home I thought "man, fuck this. I could totally just drive off the bridge." It was just a fleeting thought but sometimes it really doesn't feel worth it. It feels like an act of futility. But you just gotta keep going because you love it. And you'll never get to where you want to be unless you keep getting up on stage and pushing yourself.

  5. I would like to write for a show but I'd honestly love to make my living traveling the country headlining at clubs. It's just a blast to be onstage and I love the instant gratification.

  6. It was just sort of a natural transition. At one point I won a contest at the Pittsburgh Improv and started getting work there because of it. But as for other gigs a lot of it is just knowing people and them people thinking you are funny and nice.

  7. It honestly depends on the week. Sometimes it's 1 set Sometimes it's 7.

Im_Making_It_All_Up3 karma

What's your most controversial joke? Whether it's yours or one you've heard, maybe both for a bonus?

TimIsWin1 karma

I honestly don't have very many controversial jokes because my jokes are mostly silly. I do have an Anne Frank joke though:


NotForFap3 karma

What is your favorite food to eat your feeling away with? Mine is buffalo chicken and mayonnaise

TimIsWin8 karma

It's funny, you don't even realize how appropriate this question is to me and stand up. Here's a story:

The first time I did stand up, things went well. I got laughs throughout and I got off stage feeling good about myself. I had high hopes and I was ready to get back on stage again. The second time was way way worse. I didn't get a laugh for five entire minutes. It was just stone cold silence and awkward shuffling. I felt miserable.

I had gone to the show with a friend and she was driving. The whole ride back I had my head against the window just wallowing in self pity like a little crybaby. At one point there was a few minutes of silence and I (100% serious without even thinking about it) said "Man, fuck. I could probably eat an entire lasagna right now."

So pasta. Or buffalo chicken with mayo. That sounds good.

thatjacob3 karma

Has your opinion changed over the past 4 years? Are Cheetos chips?

TimIsWin7 karma


donteatpoop3 karma

I still laugh every time I think about your 'I broke up with my girlfriend because she likes to deep throat' joke. It kills. Just told my boss, he's crying.

Keep being awesome.

Besides being funny, what other talents do you have?

TimIsWin1 karma

I don't have any other talents that's why I try really hard to be funny. :(

ThePuffingtonPost3 karma

What's your creative process like when you write your material?

TimIsWin1 karma

A lot of times it's just me pacing around and talking to myself. And trying out four dozen different punchlines before finally deciding which one to go with. And then taking that on stage and when it doesn't work picking another punchline.

decentlyconfused2 karma

Can you talk a little about "running" the business of being a comedian (Finances, publicity, etc)?

Or is it just enough to "be funny" and everything falls into place?

TimIsWin-1 karma

There's a lot of stuff you have to do in regards to that sort of thing. I am very very bad at all of it.

wesisawesome2 karma

What percentage of your stand up shots end up in your set?

Have you started to write jokes that will specifically fit the stand up shot style?

Who is your favorite wrestler and why is it Dean Ambrose?

TimIsWin1 karma

  1. End up in the set? Well I've probably said at least 75% of them on stage at one point or another. Some of them just for a short time. Some for a long time and some only once. It's a really weird dynamic. Some things work super super well on there and just absolutely don't translate to the stage. There are definitely times where I'm like "yeah this one is just for /r/standupshots"

  2. Nah the stuff I've been writing lately is actually the opposite. I've written a bunch of new material that just doesn't work in that format, haha.

  3. My favorite wrestler is Kevin Owens because he is fat and bearded. Ambrose isn't far behind but my favorite main roster guy is most likely Rollins.

packetOFfries2 karma

Tim, I am a huge fan of yours ever since I saw a something you posted on /r/standupshots about being ginger... I think

Do you have any tips for any aspiring teenage standup comic?

TimIsWin2 karma

Hmmm I don't even know what that joke would be, haha. Appreciate that!


Get on stage. Whether it's at coffeeshops or school talent shows or wherever you have to go, get on stage. Since you're so young it's gonna be hard to get into clubs and bars so just try to get stage time wherever you can. In the meantime just try to be funny in as many ways as you can. Produce sketches on youtube, post vines, write jokes on twitter. Anything you can do to put yourself in the mindset of being consistently funny.

ThePuffingtonPost2 karma

No redditing?

TimIsWin3 karma

Sure why not? It can suck you in though. I've definitely lost a few hours commenting on things.

XaosZaleski2 karma

I know that you're somewhat into pro wrestling - what are your thoughts about tonight's WWE Extreme Rules card?

TimIsWin0 karma

I'm already disgusted at the fact that Ziggler is going to be kissing Sheamus' ass.

Ambrose and Harper are going to beat the shit out of each other.

I'm hoping the main event goes like this:

Rollins sets up for the curb stomp near the ropes. It looks like they're going for a repeat pop up RKO spot from mania but instead Rollins is launch into the air where he grabs the cage. He scrambles up and over before Randy even figures out what the fuck is going on.


YoureTheNews2 karma

What is your favorite joke that totally failed when you used it live?

TimIsWin8 karma

"Growing up I always thought The Red Sea (C) was the third book in the Scarlet Letter trilogy"

It's so so dumb but it made me laugh out loud when I came up with it.

Guckalienblue2 karma

What's your favorite way to eat pierogis?

TimIsWin4 karma

Every way

Guckalienblue2 karma

How do you like your scrapple

TimIsWin1 karma

With Syrup!

Guckalienblue3 karma

How do you like your yuengling

TimIsWin3 karma

In my belly

Guckalienblue2 karma

When can we expect more Pig Pen raps

TimIsWin1 karma

Very soon pigpen always writing

Guckalienblue2 karma

What's a body part I should be proud of?

TimIsWin1 karma

ur butt

Hamsterxl2 karma

Favorite place to perform ? And why?

TimIsWin1 karma

Arcade Comedy Theater in Pittsburgh. It's a great black box theater venue. The crowds are generally young and vibrant and ready to laugh. The staff is great. I've had a blast every time I've performed there. Check em out if you're ever in Pittsburgh www.twitter.com/ArcadeComedy

ohseven10982 karma

Do you still do music at all? Your vox for FTF were pretty solid.

TimIsWin1 karma

hahahahaha omg who is this

TibetanLesbian2 karma

Have you been close to getting booked on Scorch's PFG-TV?

TimIsWin1 karma

i dunno what that is

TommyPills2 karma

Hey, who do you look up to in the world of comedy? And what comedian do you think is killing the game right now?

TimIsWin1 karma

I look up to lots of people to be honest. Anyone who has managed to make a name and career out of this is generally gonna have some qualities to look up to.

As far as killing the game right now I'm gonna with someone who isn't yet well known. My buddy www.twitter.com/aaronkleiber is an absolute killer who is on the rise at the moment. Dude's getting attention from a lot of different places and he's one of my favorite local acts to watch. He just headlined a bunch of sold out shows at the Pittsburgh Improv a few weeks ago. Definitely a dude to watch out for.

Zim_Zam_the_Spaceman2 karma

Who is your favorite comedian? Huge fan, by the way.

TimIsWin5 karma

My all time favorite comedian is Mitch Hedberg. I used to sit in my basement and listen to his albums all the time. Thank you!

thehofstetter1 karma

Hi Tim! Great to see you doing an AMA. Has reddit helped you as a comedian, either as a writer or professionally?

TimIsWin1 karma

I think the standupshots have definitely helped with writing and being concise. Also I met you on here and you put me on TV haha

thehofstetter3 karma

You put you on TV.

TimIsWin1 karma


windflail1 karma

I misunderstood you sending a link to one of your comments on twitter and called you out on it resulting in many downvotes.

On an unrelated note, how much of a difference to your career has reddit and standupshots made?

TimIsWin1 karma

Man I felt so bad about that! I checked in a few times and the votes just kept coming. I was genuinely confused about what you meant. Standupshots has made me a better writer and I've met some really cool people because of it.

iamanis1 karma

Will you be getting a haircut and beard trim ever? Big fan. Love you. You're favorite guy in the rttc group. Cheers.

TimIsWin4 karma

I just got a haircut! http://i.imgur.com/bgyZUNQ.jpg