If the comedy community had an FAQ page, "How did you get that?" would be at the top of the list. Asking isn't always popular because everyone wants to be chosen, but in my experience, asking for what I want has always gotten better results than waiting.
Before I did comedy, I worked in the music industry, interviewing bands and reviewing albums.
Before I worked in the music industry, I was a person that wanted to work in the music industry but wasn't sure how to break in. I started by writing an email to a local radio station that played the kind of music I wanted to write about and asked if they would consider me for an internship. I was 15, and there wasn't an actual internship I was applying for, but I knew I wanted to be part of what they were doing at 98.3FM. I pitched an idea of what I wanted to do, why I thought I would be great at it, and when I was available to begin doing it. I got lucky, and the right person read my email, and over the next several years, I worked my way from intern to full-time host. Once I had honed my industry skills a little, I knew I wanted to interview more prominent bands and review major release albums. When I was 19, I started a blog next to nobody read, but I kept posting 2-3 times a day. Eventually, that blog became the portfolio of writing I submitted to significant publications. By 21, I freelanced for people who granted me access to the influential names I wanted to interview.
I've approached comedy pretty similarly: I decided I wanted to do it, I found ways to practice, and once I felt confident, I started asking the people to consider me for opportunities. As silly and fun as comedy is, if your goal is to do it at any level beyond open mics, you have to treat it like a job- and it is pretty rare to get a job without applying.
If you have been consistently developing your act at open mics but haven't gotten booked on a show, the person running that show probably hasn't seen you yet. Even in a minor comedy scene, many faces cycle in and out, so it is ridiculous to expect anyone to pay attention to your growth.
In my experience, the people who book rooms are much more likely to consider your booking request if they've seen you watch their show before. Comedy is often a give and take, but it is essential to remember that attending a show is not a bargaining chip. You don't get to say, "I came to your show, so now you have to put me on." but you can tell the showrunner, "I think your show is great, and I would love to be part of it. How can I be considered?". Try saying hello in person (aka put a face to your name) and then send a polite follow-up message to the show's social media or booking email expressing your interest.
There is a vast difference between asking, "Can you book me?" and submitting your work for their consideration. Never ask a booker how to get on their show during the show. It isn't polite, and they 100% also will not remember you asked- they're busy!
If you see a show or comedy festival posting about needing volunteers, offer your help. Shows often need someone to work the door, help set up chairs, and post flyers- a ton of work goes into running a successful comedy show. Offering your help gets you face-time with people who can book you, shows your investment in making the show a success, and your respect for the showrunner's work. Not to mention it's a free lesson in show running!
A great message to send a show you have already been out to support:
Hey (booker's name OR name of show),
Last night, I had a great time at (Name of Show OR venue ). You run a fantastic room! I wanted to send a tape for your consideration and hope to perform with you sometime soon.
Thank you,
(Your first and last name)
(Link to a video/website/media kit/etc.)
If they don't reply to your message, wait a few weeks and follow up. If you still get ignored, do everyone a favor and leave it be until you have a new tape. Sometimes, no answer means no. Once you have submitted your information, you have no more power over the process- trust that they'll have you on if it is a good fit, and if not, there are plenty of shows out there.
A good video should be well lit, easy to hear, and 5-7 minutes long (unless told otherwise, this is pretty standard). Most bookers want to see unedited tapes (not a highlight reel) and are not interested in your crowd work, so keep that in mind as you try to get a new clip for submissions.