In April, while in lockdown in my apartment in New York, I got a phone call from a guy I had met at my comedy club in Aruba. We had spoken after a show, and bonded further at the poker table. He was the CEO of a music publishing company and was looking for ways to entertain his employees who had been working remotely. “There are only so many motivational speakers they want to hear from,” he said. “In fact, they are starting to become unmotivated. They’re Zoomed out.”
He asked me about doing an online comedy show for his troops, who had been working from home for over a month. I was reluctant at first; the comedy show he saw in Aruba was very very good; Aruba Ray’s is rated number one for all nightlife activity in Aruba, which I’m really proud of, and I didn’t want to lose any of my shine because of an awkward attempt at comedy through a webcam.
But I wasn’t making any money sitting at home bingeing Peaky Blinders and rewatching Game of Thrones, so I figured a new challenge made sense. If this online comedy failed, the pull-up bar I had ordered had just arrived, and I could kill a few days trying to attach it to my doorway before never using it.
So I assembled a lineup of terrific comics I had worked with before, both in NYC and Aruba, each of whom had multiple TV credits, and were very funny and reliable. I knew they wouldn’t show up on their laptop drunk.
I came up with a format that I thought would work, taking into account the attention spans of people watching comedy online that I learned from my earlier web talk show “Late Net.” When watching comedy on a computer, shorter clips of awesome guests like Fran Drescher and Chevy Chase worked far better than longer ones.
I served as host, something I’ve been doing for years on stage and TV, and I rotated through my lineup, moving along as instinct dictated. It was a bit clunky at first, there are a lot of moving parts on a Zoom show; I had to time when to highlight a comedian, how to locate and engage audience members, dropping in bits, checking and addressing the comments in the chat, and monitoring the audio flares on the webcams. It was my first time using Zoom, and the platform wasn’t originally intended to be used as a virtual comedy club.
From years of doing standup, I know how to work a crowd, but doing so through my computer, and into another person’s computer is a completely different beast. In a comedy club, you pick up on the body language of audience members, the energy of the room, and work it accordingly. With an online show you need to do the same thing, but without knowing if a person is nervously tapping their foot, or fidgeting with their date’s jacket. It’s the difference between driving a car on a clear sunny day on an empty highway versus during a rain storm in traffic at night. You know how to do it, it’s just less common, and you need more focus. And you have to keep the windshield dry.
The show went great, the audience loved it. The timing and duration of each act worked, interspersing banter with the crowd paid off, and I discovered that spotlighting a person on Zoom during an online show is the new way of being featured on the Jumbotron in Times Square. The good-natured joking online is missing while working at home, and it was a fun way to connect with colleagues in a fashion never been done before.
From that first positive experience, I knew there was something there. I felt really energized for the first time since the quarantine started, with the most excitement prior to this being the purchase of an air fryer. I started bringing Aruba Ray’s Comedy Shows online every week, modifying the format, and also learning which comedians were solid at performing on a webcam. There are many comedians who are outstanding onstage but terrible online. Some just don’t have an interest in it. Others would like to participate, but just don’t pop through the screen.
I sold tickets to people from my mailing list who had presumably seen me at The Comedy Cellar in New York or in Aruba, and donated the ticket sales to charity, (a food bank in Aruba happytogiveback.com, and a fund for unemployed comics in NYC, supportcomedians.org). There were hundreds of people at home who wanted to connect in an upbeat way, wanted to laugh, and wanted an escape that broke up the monotony of quarantine.
I officially formed Comedy Cloud in May. Sixty-plus online shows later, the process has been honed. Word of mouth has brought in a variety of clients, from nine webcams to nine hundred, with colleagues zooming together to form an audience from all over the world. For one company, Spirit Music Publishing, their Comedy Cloud show simultaneously connected their employees in Australia, England, Los Angeles, Nashville, and New York. Everyone was watching in a different time zone, but had an outstanding bonding experience, with the biz dev team sipping their morning coffee as the copywriters enjoyed their port wine.
I have produced and hosted live interactive online shows for company happy hours, lunch breaks, and award ceremonies. There have been fundraiser events, country club events, and using the show as a device to help companies attract new clients. There have been more financial services companies and law firms that want to laugh than I ever imagined.
I’m incredibly pleased with the growth and success of this unexpected venture. For now, traditional standup comedy is not happening. Yes, there is the occasional live show in a parking lot or field. But with Comedy Cloud, I have done as many as nine shows in a week, any time from noon to midnight. Online comedy is without question far more challenging than a traditional live standup show. But very gratifying.
And every show is different. I have a core roster of comedians I work with, but I can customize the show for any group. I have put together a lineup of all female comics for a women’s organization, a lineup for a company composed of all 20-somethings, and a roster of Italian comedians for — you guessed it — an audience of Italians.
This has been a bizarre and unprecedented time for everyone, and if overworked, lonely people stuck at home feel rewarded, I do too. Comedy Cloud has helped me fill a void created by the pandemic, and has given me another way to stay connected to people and entertain them. Workers are thrilled for the break, comedians are happy to be working, and I am pleased that I started something new that is personally rewarding. There are only so many masked conversations my doorman and I can have at two in the morning.