I have an upcoming one-nighter where I’m co-headlining with a comic I’ve never met or worked with. We’re both doing the same amount of time and both making the same amount of money. So who goes first? She’s a female comic four years younger than me, but I’m going to offer to go first because I don’t have an ego. What does it matter what the middle of Illinois thinks (no offense middle of Illinois) because they’ve never heard of either of us, and probably won’t hear of us again. If the other comic tells me she would prefer me to go last, then that will work to. Here’s what ultimately will decide it…Who works cleaner?
The cleaner comic should work earlier in the show because once you take an audience (down?) to a certain level, it’s really tough to bring them back up. That’s how you should approach your set as well. Save your dirtier stuff until the end. If she works clean then I’ll have no problem with her going first, but if not, I’d prefer the opening spot.
This can apply for other shows as well with more comics. You should have a pretty good idea the amount of “blue” in each comic’s act and can loosely arrange your show from that. Again, do this with your act as well.
A few weeks ago a first-timer did a joke a piece about Jesus and (insert the worst thing you can do to Jesus) towards the end of his set. It was epically awful, but then he followed it with a bit about “Why does cotton advertise?” The funniest part was following the Jesus bit with a simple observation piece about cotton (If you’re that comic and reading this know that a few people pointed out that someone’s already done that cotton bit…also, drop the Jesus bit).
So again, ignore your ego and remember that it’s easier to follow clean than dirty. On a Bob & Tom Tour a few years ago a lot of comics all decided to let April Macie close that show out. Though they were bigger names and more successful, no one could follow how dirty she was. Everyone was happier once they made this adjustment.
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Don't Wear Shorts on Stage 
I don’t know that most audience members know, or care, about the order of the show in how it relates to ‘headliner’ vs. ‘not headliner.’ They just know they went to a show and had fun. On a rare occasion when an audience member tells me they liked everyone but then continues to tell me whom they liked better I just point it “It’s entertainment, it’s not a competition. As long as you had fun, we all won.”
Right! Thus making ego even sillier to worry about. Sometimes I wish the audience secretly knew the discrepancy in pay between comics though. “That first guy wasn’t that great.” …Well yeah, he’s been doing it for eight months and just pocketed $25, cut him some slack!
Well, if he’s been doing it just eight months why is an audience paying to see him? Unless it’s a short set and he was introduced as a new comic they’re giving some time to.