I was moments away from being on Oprah! Okay, 2 days away. but I was darn close to getting my BIG break. I was scheduled for the segment. I had the plane tickets. I was ready. And then  . . .  something completely beyond my control happened.

Rewind to a few weeks earlier. My best friend Rob, who was also a comedian while keeping his lawyer “day” job, called to say that one of his college friends was a producer on Oprah, and that they were looking for an unknown comedian! Perfect! I was as unknown as you could get at the time.

It seems Oprah was doing a series on fulfilling your dreams. She was taking people who had always dreamed about doing something and helping them achieve it. Like if you wanted to be a pilot, she’d get you some flying lessons and off into the skies you’d go!

Well, there was a housewife in Texas

who always wanted to be a comedian. Sooo, Oprah was having the fantastic comedian Wanda Sykes work with her for a week. Wanda would write jokes with/for her and help her with delivery and all the other gazillion things that go into being a comedian. After a week or so of this “comedy immersion,” the woman would then do a 5-minute comedy set at the Washington, DC Improv. They would tape the show and then – this is where I come in – put her tape up against an unknown comedian’s tape (me) and let people vote on who was the “real” professional.

This was so perfect for me in many ways. My video tape that I used for marketing was also taped at the DC Improv (my home club) so the tapes would be similar, AND I was already scheduled to be in Chicago for an event the day that our tapes would air on Oprah! Wow, could it have been more in sync?

Yeah, it was so perfect except for one tiny fact. You cannot become a comedian in a few short weeks, regardless of having the best of the best comedians, Wanda Sykes, helping you. Apparently this became very obvious when the newbie went onstage at the Improv. Rob called me after the show and gave me a heads-up saying that, in his opinion, they could not put my tape next to this person’s tape because there would be no contest. He said that aside from messing up material, the newbie went over her time, and had no stage presence. Stage presence is what you get from the good, the bad and the mediocre gigs; you can’t rush this process.

Sure enough, as Rob predicted, the producer called me the next day. They were very nice but said they had changed the segment and wouldn’t be needing me. I was crushed that I wouldn’t get my shot on Oprah, but also a little pleased that someone couldn’t waltz in and become a comedian overnight. I have no idea if the segment aired; I couldn’t bear to watch for it. 

Morals of the story: 1. The easier something looks, the harder it probably is to do so don’t skip the work in-between that makes you good. 2. Don’t put too much weight on fame. I never needed Oprah to be successful. It would’ve been nice, but, in hindsight, I’ve had a great career, without being famous.

Check out my website at TheWorkLady.com and other blog stories such as this one here about 400 Square Feet to Success.

400 Square Feet – it helped me tremendously in my comedy career. For anyone looking to make the jump into comedy writing full-time, or really anything other than what you’re doing, this article is for you!

If you want more of my articles like this, I publish them every week (usually Tuesday) on my Facebook Business page – click here

Here’s the Article:

My first “apartment” (if you could call it that) in Los Angeles was 400 square feet. There were 3 places to sit AS LONG AS SOMEONE HAD TO GO TO THE BATHROOM. It had a chair, a futon and a toilet. My cat was confused about the futon because she knew that when we lived in Virginia, she could get on the bed but not the couch . . . but in her cat brain, the rules changed when the bed TURNS INTO a couch.

And it wasn’t in a great section of town. My friend comedian/keynote speaker Frank King used to say “Jan and I are such good friends that I’d take a bullet for her. And when I saw where she lived, I thought I might have to.” About once a week the cops would shut down my street as they chased fugitives by car and helicopter. Extra excitement! I got so used to this that on one July 4th, as I was headed out to the driving range with my golf clubs, I ran into 2 cops trying to get into my gated parking area. They asked if I could click them in, so I did.
 

Thinking nothing of it, I walked in with them, one on each side of me, when suddenly, they both drew their guns and pointed the guns directly at the recycle bin. One cop was shaking a so hard I’m not sure how he could even aim. It’s like he just now realized he’s a real cop with a real gun. I was shaking too because I didn’t have a gun, just a 9-iron.
 

I hightailed it up to my car, dove in, and called Frank to say “I may have to take a bullet for me too!” I realized that if this criminal gets away from these shaking cops, I’m the only one with a clicker and a getaway car!

After a couple minutes, I looked up, and the cops had him in cuffs. Whew! Then one of ‘em yelled, “hey, can you click us out?” I did.

That apartment may have almost killed me, but it also saved me. Though I looked about as unsuccessful as you could get, I actually felt pretty good about living there. Lots of people move to Los Angeles or New York, hoping to find fame and fortune. They get an expensive apartment, in a nice part of town and then realize that that they need to take on a waitress or bartending gig to actually pay for it. My 400 sq foot apartment in that dicey neighborhood was $400 bucks a month . . . It gave me the FREEDOM and the ENERGY to focus on my career and figure out what I was doing without the pressure of needing a lot of money. That strategy worked!

My advice – don’t worry about how something looks to others; you just have to know why YOU are doing it. If it fits in with your plan, then go for it!

Check out another story from my comedy career by clicking this link!

Getting my name in lights on the Las Vegas strip was a bumpy road, and it really wasn’t what I was aiming for. But it happened many moons ago and it’s a great story. And it all has to do with my comedy writing!

Here’s what happened. . .

“One-nighter.” It’s a word (or words?) that conjures up all sorts of memories – for some people it’s memories of too much alcohol. LOL. But if you’re in entertainment, it actually means a gig that is one night long – usually a bar gig.

Back when I worked comedy clubs, the club would usually run Tuesday through Sunday night, and then be dark on Monday. So, a local bar in town would have the comics come over to perform. We’d make some extra cash and the bar would get a great show with nationally touring comedians.

The problem was, many times the bar didn’t advertise the show, so when customers showed up on a Monday night, trying to find a “traditional” one-nighter (ya know, the one with alcohol), they got comedy! Plus, bars usually aren’t set up great for comedy –the customers want to drink and talk, the mics stink, no mic stands, AND Monday nights there may be a football game on the TV. The bar owner would usually turn off the game and send us up there. How fun for us!??

These gigs were tough for me, and usually not my “style.” I once had a bar owner meet me at the door. Take one look at me. Take one look at his audience/bar. And declare “you aint got any of them thinkn’ jokes, do ya?” Like I was going to accidentally educate his crowd. Yes, I had “thinkn’” jokes. And yes, they didn’t go over well.

I had some tough nights in one-nighters, and no, I’m not opposed to drinking or carousing, but from my angle as an entertainer, I hated these bar gigs. Many nights I skulked away after a bad set, while the other comics, who had more “bar friendly” material rocked the room.

One comic in particular that I worked with a lot at these gigs, I’ll call Tom, did phenomenal. He had pot jokes, and drinking jokes, and sex jokes. He really had the crowd rolling. My jokes on kids and work did not compare. But I kept doing my thing because I realized that these bars were not the venues I wanted to excel at. This led me to some excruciating nights of bombing for me, but I stuck to my guns.

Years later, after I had (thankfully) moved on from the bar gigs, I ran into Tom in Las Vegas. He was there for vacation, and I was working at the Excalibur hotel on the Vegas strip with my name and face in lights up on the big marque. He said “Wow Jan, you’re doing great! You’re in Vegas. When I started out in comedy, I swore I wouldn’t do any pot jokes. I now have 60 minutes of pot jokes. I can’t get hired in Vegas.” He did not stay with his plan, possibly because it got too hard, and it was just easier to write pot jokes to appease the audience in the moment.

Lesson learned: Don’t stay on the path that is given you if it’s not what you really want.

Keep on doing your thing until you find your fit. It is so worth it!

If you’re looking for a GREAT speaker for your next event, check out my website www.TheWorkLady.com

(The picture above is my first time working Vegas. Ironically I didn’t have enough money to buy a camera! Luckily the club manager loaned me one)

Check out my other stories – this one is Five things I learned from Forensic Files! https://www.comedywriterblog.com/2023/09/01/five-things-i-learned-from-forensic-files/