How to become a headliner (I’m trying to learn too)

This week I fell into some headlining spots at the St. Louis Funnybone (Wednesday and the Saturday midnight show).  And before I even get into this entry I’m not claiming I am one, especially at an A room.  It just made me wonder what steps I needed to take to get to that point.  The first thing is that I need to be comfortable doing at least a strong forty-five.  As a feature you can get away with a “solid” (insert time), but as a headliner it has to be strong.  So just like in the jump from MC to feature, it’s not just a quantity of minutes, it’s the quality of what you’re giving the audience.  Over the years though, I’ve worked with a number of headliners who weren’t any funnier than me or a lot of the other comics at my level.  But what’s the one thing they have?  Experience.

So the first step to being a headliner for a week at a comedy club is getting a lot of time as a headliner at one-nighters.  I don’t have a ton of experience with that so I went to someone who did, Steve Sabo.  Steve also books dozens of rooms so he was the perfect person to ask about what bookers look for when promoting features up to the headlining spot.  He also mentioned what doesn’t work so I’ll talk about those things first.

When a venue calls to give feedback on the show and the manager says, “That middle guy should headline!” bookers can tell the manager was instructed to say this from the feature as a favor.  Managers don’t talk like that in bars who host these shows.  They simply say if the person was funny or not.  He also advised against trying to be hard to follow by being extremely filthy and talkative with the crowd.  As a feature, you shouldn’t be relying on any crowdwork in your set (there’s much more about this in my book, Don’t Wear Shorts on Stage).  There are better ways to become tough to follow. 

It’s a tough leap to make because most of the headliners out there aren’t going anywhere.  There’s no higher level so the market becomes saturated and competative.  Sabo stated that a headliner’s set needs to be more than just jokes.  It has to have that extra layer.  I’ve seen a lot of headliners have a theme, message, or some extra variable that makes their show more than just 45-60 minutes of jokes.  Even the setups need to be funny.  No matter how funny a comic is, they have to have experience to get by and make an audience laugh under any circumstance.  There are tough spots a comic just won’t experience in his or her first five years.  Today’s headliners are prepared for everything.  So how does Sabo personally start considering someone to bump up?  He waits until he has three different venues rave about the feature. 

The biggest challenge or concern I have when headlining is, “Can I fill my time?”  I tend to slow down (which I actually need to do anyway), but I sometimes put in older jokes that I shouldn’t really rely on anymore.  Usually I get the five-minute light and I still have fifteen minutes of better material that I can no longer fit in left on my mental setlist.  So my next goal is to become comfortable with how a solid forty-five minutes feels (I’ll work on making it stronger as I write more this year…I have a strong thirty plus, but not 45).  I have a few chances coming up this fall so I’m excited about that.  If you have questions, ask a booker or club manager.  There are a lot of other factors that go into it but this should be a start.  Good luck.


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