A Cup of Coffee with Geoff Ross

Recently, we were able to sit down and catch up with Geoff Ross; an improviser, filmmaker, and all around good guy.  In this conversation, we cover a variety of topics including the differences in comedy across the country, the lengths one will go through to impress a girl, and how comedic influences don’t always come from television.  

Brace yourself - there will be bits.  



IB: In the truest sense of improv, can I have a one-word suggestion to start this interview?


GR: Your word is Hunger.

IB: When I think of hunger I think of grabbing lunch.  In my experience the funniest bits always come out when I’m out to lunch with a friends and that’s when the bits come out.  That seems to be when the magic happens.   Did you have a similar experience that drew you towards comedy?

GR: This would have been early on.  My first audience was my three brothers.  When I discovered at a fairly young age that I could make people laugh on demand, it was the most fun I could have.  It was a great feeling knowing that I could get all my brothers on board.  Personality wise, we were very different people.  We all got along, but we had very different interests; [my brothers] were very similar.  I always felt that they thought I was doing my own thing out of spite, but I just didn’t share their interests.  When I realized I could make them laugh, that became something we could all do together. 

When I discovered I could make adults laugh and that they enjoyed that I was around that was another big step for me.  We’d be visiting with friends and all the kids would get together and do one thing and the adults would go off and do something else.  I would get bored with the kid thing pretty quickly and wander over to see the grownups and they seemed to find me amusing.  I didn’t really know why or what they found amusing, but I enjoyed the fact that I could do that. 

That continued to develop and I started getting involved in performance activities at school and performing kind of became my thing. 

IB: So it wasn’t like you were walking through the lunchroom, tripped, food went everywhere and all of a sudden you realized, “Oh my God, I can make people laugh!  These pratfalls… they work!”

GR: ‘Can you believe it?!  Chevy Chase was right!’  No, I never had that specific moment where everything just clicked.  When it became the most valuable for me was when I moved from Illinois to Minnesota because I realized I could make friends really quickly by the fact I was funny.  I realized, “Oh this is a valuable social skill… this can get me out of a jam!”  That’s where being amusing became critical to me as a person.  That put a stop to what would have probably been loneliness and isolation in a new place. 

IB: Being uprooted and moving right before high school can’t be easy.  I’m sure you felt you had to adapt super quick.

GR: It was a big change.  It went well, but it was a big change.

IB: So from Illinois – a comedy epicenter – to Minnesota.  

GR: Oh yeah.  We lived in the Chicago area, so comedy was everywhere.  I got to go to a show at Second City on a family trip back to Chicago.  I have no idea how I got in; it was definitely not a show aimed at kids.  It ended up being a show with a young Horatio Sanz and a young Amy Poehler before they were ‘people you would know.’ It was really cool seeing them perform just a few years before they were on SNL. 

IB: Was that your first improv experience?

GR: That was my first improv.  The show I saw was called Paradigm Lost.  Some of it was scripted and some of it was improvised and all I can remember is being legitimately entertained.  I knew there was a lot of material going over my head, but [judging by] who was laughing at what, I could tell who each joke was aimed at.  I made mental notes like “Clearly this is an adult joke and I don’t know what it means, but I should probably laugh!” 

IB: Compared to Chicago, what did you think of Minnesota?

GR: I lived in a town called Rochester, MN.  It’s known for two things – the Mayo Clinic and being an agricultural center so there were a ton of doctors and legitimate farmers – and those were my classmates.  I found it really interesting that I was living in a place full of people that normally would never interact.  Minnesota as a place is… weird.  There are not a lot of minorities in Minnesota, which was a change for me, but it’s still a progressive state. 

I didn’t get into performing comedy while I was there.  I didn’t really consider performing comedy until I went to college.  While I was in Minnesota, I did a lot of plays.  I wound up auditioning for the school play because of a girl I was interested in at the time.  I was hanging out after school and she said casually ‘Oh, are you auditioning for this?’ and I said ‘…Yes!  That’s what I’m doing here.’  So I auditioned and wound up getting the lead role.

IB: That’s fantastic.  What play was it?

GR: It was the musical FAME.  

At this point, Geoff and I start singing the theme song.  No one else in the restaurant was impressed.

IB: Here’s something strange about FAME - I didn’t realize that FAME was based on the high school that 2Pac went to. 

GR: Wow I didn’t realize that until right now – 2Pac went to a performance high school? 

IB: Yeah – he went to the FAME high school and I think that’s how he and Janet Jackson became friends.  Then he was on ‘A Different World’, and then he joined Digital Underground, which brings us to… today.  Nothing else really happened with 2Pac, right?

GR: Nope, that’s the end of his story.  They did The Humpty Dance and that was it.  What ever happened to him?  Did he ever get out of Digital Underground? 

It would be hilarious if everyone’s common knowledge of famous people stopped RIGHT before they got famous.  ‘James Brown had this back up guitar player… Jimi…. Hendrix?  He seemed really talented.  I wonder what ever happened to him.’

IB: It would be like knowing everything there is to know about Star Wars Episode I: The Phantom Menace and nothing about the rest of Star Wars.

GR: I wonder what happened to that plucky little kid in Phantom Menace?  He seemed like he was headed for big things. I wonder why they never made any more of these movies?  I could see myself watching at least five more of these.  Oh well – a mystery forever!  Hollywood – am I right?

IB: So where did you go to school?

GR: One hell of a segue.  I went to New York University – I went for Film & Television.  When I was there, I became aware of the UCB Theater.  I knew they had a show on Comedy Central, but I never watched it.  A friend of mine told me about the theater and suggested I check out a show.  I figured a show in New York?  That’s got to be like $600 bucks, so imagine how excited I was when I found out it was like $5 and wound up being like the funniest thing I’d ever seen. 

Amy Poehler had recently started on SNL and she was still performing regularly at UCB.  So there is this celebrity… and she’s doing a show… in a basement… and it’s hilarious.  At the end of the show they mentioned that they offered classes, but I didn’t think it was for me.  I figured I was funny enough for my friends, but not in a way that would translate into the type of performance I had just seen.

IB: That’s very interesting considering the conversation we’re having right now.

GR: I kept telling myself that I should take classes, but would always talk myself out of it.  New York for me was actually a fairly depressing place.  I sailed through high school and with that came terrible study habits and as it turns out – college is MUCH harder.  Socially I wasn’t as successful as I had been the last time I made a huge move, so things weren’t going great.  I was alone, and not doing well, and shit sucks, and everything was a lot harder.  I didn’t realize how big of a mountain the Film & Television world was.  I figured I’m going to the best school for this medium and that will be my foot in the door and not even that is enough in most cases.  The existential problem of spending a fortune and still not being able to do the projects I wanted was so hard. 

One day I knew that I had to just feel better.  I was tired of being miserable all of the time; that is just not acceptable.  At this point I had been considering taking improv classes and I told myself that if I take the class and it sucks, well, I’m out a few hundred bucks, but at least I’m trying to do something that will make me feel better.  On the plus side, if I had fun then GREAT – I had fun and that’s what I was paying for.

The first class I took was with Kate Spencer.  Their 101 class is similar to ours in that the main goal is to just get on stage and play and have fun.  I was getting addicted, and I think that’s how you tell if you’re into it or not – if you feel compelled to keep going.  Not that you’re owed anything at the end, but if you just want to keep going and going. 

For the first time in New York, I felt like I was meeting people that were like-minded – that didn’t regard me as a weird person but as a funny person.  It’s a difference that matters a lot.

IB: Agreed.  What kind of steps were you taking to perform outside of the class structure? 

GR: After my 401 class, me and several of my classmates formed Casual Sex Offenders, also known as CSO.  It was a lot of fun performing with them – they still perform quite a bit in New York.  Performing with CSO was my first experience with performing regularly.  At this point I was really addicted to it. 

Eventually I moved to Boston for grad school to continue my film studies at BU.  The lesson I took from my New York experience was that I needed to get into the improv scene much faster so that I could avoid all the same mistakes I had made previously.  My first class at ImprovBoston was with Sasha Goldberg.  One day she mentioned that IB was holding auditions for Harold teams.  At that time IB was primarily focused on short form.  Coming from UCB I was very familiar with the Harold, so I auditioned as soon as I could.  I thought I did ok.  That night I got the call that I had made a team.  I’ve been on a Harold Team ever since.

IB: What was the show schedule like at that point?

GR: In 2009, Harold Night was fighting for it’s spot on the schedule.  We were struggling to fill the studio space because it wasn’t something that our audience was really familiar with.  But we were a scrappy group and we had ambitions, and we were all determined to do well.  A lot of serendipitous things happened and we were able to gain some momentum.  One of the main stage shows, Bastards, Inc., was breaking up so that created an opening in the schedule, which somehow Harold Night was able to get into.  We were more or less on probation at the start – there were certain audience goals we had to fill just to keep that spot.  We were able to do it and now Harold Night is a tradition.

IB: Was this a big change from what you were used to in your previous improv life?

GR: If I were in New York, I probably would not have gotten the chance to contribute at the same level.  When there are auditions in New York, 400 people show up, so I wouldn’t have had the same opportunities.  What this forced me to do was really focus on my craft and make sure I was putting on the best show possible because now there is an audience that is paying to be here.   Because we were still earning a reputation we knew we had to be good.  We had to give the audience a reason to tell their friends they had to come see the show. 

I took a class once with Shannon O’Neil from The Stepfathers at UCB and she once said – and I’ll never forget this – ‘If you guys really want to get good at this, you need to be practicing outside of this class.’  That for me was the differentiator because I realized that for me, this wasn’t just a class.  This was something that I really wanted to do and I had to find other people who felt the same way.  At UCB, the 201 level is that breaking point – that’s when people figure out if they’re going to do it or not do it because that class is when it starts to get harder and notes start to get really specific.  That stood for me because the people who continued were now surrounded by other people who wanted to get better. 

I tell my classes something similar now – if they really want to get better they have to find a way to somehow get more practice in and keep working on things outside of class.  I’m not going to make them do it – it’s something that you have to want to do.  The people who say ‘yes’ to that challenge are the people who become good.  They don’t just say ‘I’ll pick it up in the next class’ – they say I’m going to somehow, someway find a way to keep doing this as much as possible.  I’m going to get my like-minded friends together and whether we’re doing shows or just practicing in someone’s living room, we’re going to work and figure it out and see shows and just keep at it. 

IB: I feel like the shows you see in Boston are more than just watching someone actively doing their hobby – you’re watching someone do what they do.  They are constantly trying to get better. 

GR: Boston is a unique scene in that respect because here you get rewarded for good work.  If you work hard and really refine your act, there are opportunities to be had.  The openings are small in Chicago, New York, and LA because the markets are so flooded.  So even if someone has a tremendous amount of talent, they don’t always get the opportunity to use it because the openings are so few and far between.  They don’t always have an outlet.  That’s why I always liked the independent scene in New York.  The independent scene in Boston is getting stronger as well – it’s much better than it was when I started here in 2009. 

IB: Having done comedy in places several different cities, what is it that you like the most about doing comedy in Boston as opposed to a market like New York or LA?

GR: In my experience audiences in Boston want you to do well.  The audiences here are ready to laugh at what they’re seeing on stage.  The reason why I think that’s good is because it’s very welcoming when you’re trying out new forms and different things.  The audiences here have the mentality of ‘Hey man – I’m ready to see whatever weird thing it is that you’re trying out.’  I’ve only recently started doing character monologues which can get weird, but I’ve had audiences that wanted it to work – and you can feel that.  


It wasn’t an antagonistic mentality of ‘you better make me laugh’ like you might get in some larger markets.  I think that comes with the territory because in those other places there are so many options.  They’ve seen huge acts perform on a regular basis because that just happens to be where those acts are based. 

One of the aforementioned Character Monologues

IB: I have a few friends that are cast members at ImprovOlympic in Chicago and they have a much different philosophy and approach to comedy than Second City does, which is a much different approach from what Annoyance does.  So you’re right – the audience probably has a much different mentality because they don’t have to be there. 

GR: That’s a big reason why I encourage people to do comedy in as many different places as they can.  Try to get into a festival show, or try to get a set somewhere as often as you can.  That way you know what to work on and you can continue to improve.   It’s so much harder when you don’t know anyone there.  The plus side is that if someone in a new market tells you that you did well it really means something because they don’t have to do that.  They know that you’re going to vanish tomorrow – they could tell you to your face that you were terrible. 

It’s somewhat harder to start in one of the big markets.  When you’re starting you don’t know really know what your style is or what your comedic voice is and the audiences there will let you know how you’re doing almost immediately.

IB: ‘C’mon kid we’re not paying by the laugh.  Let’s go.’

GR: Exactly – ‘c’mon sweetheart.’  I’ve always appreciated that so much about Boston.  It’s a very welcoming and supportive community not just for comedy, but for all the performing arts. 

IB: How much of your personal creative aspirations to you carry over into teaching classes? 

GR: Right now I only teach 301, but I’ve been toying with the idea of teaching 401 to see if I have prepared any of my students at all to move along into the higher levels. 


IB: I think about it like this: 101 and 201 are kind of like sixth grade math.  There’s addition, subtraction, multiplication, and long division and as long as you have a piece of scratch paper, you’ll be able to figure out the problem.  301 is like jumping into algebra.  Now there are variables and you have to solve for X.  There are patterns you need to draw and a story you need to be able to convey to the audience as a group without discussing it during the show – you all just need to be on the same page.  It’s a tough jump to make and a difficult muscle to start stretching.  401 isn’t as hard because the groundwork has already been laid down and now you’re drilling the new skills you’ve learned. 

GR: It can be terrifying.  I can be harsh in my classes and it’s not because I’m picking on people but because it has to be tough now so it goes easier in front of the audience.  I have to be harder on people in class because during the show there’s a billion things that are going to happen on stage and you have to remember all of it because you have to bring it back two more times in 20 minutes.  You’re going to have a better time if you really know the form and I promise that it’ll be more fun then if it’s much harder right now. 

Eventually you get to the point where you’re not worried about the structure because you know it and you can just focus on having a good time even if that isn’t today.  It’s like if you just learned how to play baseball– it’s a complicated game.  There’s a lot of rules.  Eventually – you’re going to enjoy it. 

IB: If someone reading this were on the fence about getting involved in comedy, what would you say to that person?  Please keep in mind that you are an instructor at ImprovBoston.

GR: Ok so don’t mention that this literally pays my bills?  Alright.  I would tell that person that I have been in your shoes.  I’ve been on the same fence.  You owe it to yourself to see if you like it.  Take the class — you don’t have to commit to every single level on the first day.  If you don’t like it, that’s fine.  It’s not for everyone.  But try to do something outside of your current comfort zone just to see what it feels like.  One thing that improv can do for you is show you the world through different perspectives.  Getting on board with people you don’t know but have a connection with…. It’s like a lifestyle change.  People who advance through improv really have a new way of moving through everyday life.  Give it a shot.   


As it turns out, 2Pac did NOT go to the actual Fame High School, but DID go to a performing arts school.  You learn something new everyday.  

You can see Geoff Ross perform at ImprovBoston Thursdays at Harold Night, or right now on YouTube through Respectability Films.  Follow Geoff on Twitter at @geoffisfamous.  You’ll be glad you did.