The Penthouse on Seymour has many allures.

There’s the simple fact that it’s a strip club. Then there’s its truly illustrious musical history. Then there’s its marquee.

For many years now, The Penthouse has used the sign above its entrance for witty quips that simultaneously promote itself and poke fun at itself.

“THE WRECK BEACH OF NIGHT CLUBS”, reads one.

“BRALESS SINCE 1947 STRAWLESS SINCE 2018”, reads another.

They change about once a month, giving people a very good reason to keep coming back—even if only just to walk by and chuckle.

Fun, flirty, and a little dirty, these signs have become their own Vancouver landmark. And they’re all thanks to a guy named Benjamin Jackson.

Originally from Ontario, Jackson has worked at The Penthouse since 2015; he started as a barback and eventually moved to a role as a bartender. These days he’s the bar manager, social media manager, and prolific “sign guy.”

After meeting him at a recent Secrets Of The Penthouse tour, we caught up with Jackson via phone to learn more about his very niche craft.

So. How did you originally find yourself working at The Penthouse?

It was through a friend. I had never worked in a bar or restaurant or anything in the service industry before The Penthouse. One of my best friends, Matt, was a bartender there—he still is. This would have been back in 2015. And I guess as one does when your friend works at a strip club, you go visit your friend all the time. So I was just doing that. And then over a few drinks every now and then I’d be like, “Hire me!” as a half joke. I wanted to be a bartender, but I had no experience. One day I got a phone call from Matt and he said, “Hey, we need somebody tonight.” I obviously panicked. I was like, “Full disclosure, I have zero experience,” but they knew that. Matt said, “We don’t really need a bartender—we just need a barback for the night.” Which is a completely different job—another one that I had zero experience in. So he met me down there and showed me the ropes: cutting limes and changing a keg. I was completely new to everything. That’s how I got my foot in the door. From there, I was persistent. I knew I wanted to be a bartender, so I stuck with it and then more opportunities came about.

When did the sign stuff start?

That would have been shortly after I started, I want to say 2016—2017 at the latest. When I started, I still remember quite vividly that the one side of the marquee said, “BOOK YOUR STAG NOW” and the other side said something along the lines of, “I WISH YOU WERE BEER”. So I said to my GM [general manager] at the time, “I can do better than this.”

Pokemon Go was released in the States before it was released here—only by a week or two, but it had blown up so big in America that it was huge news all over the world. We knew it was coming to Canada, and I think it was right before the release. [Editor’s note: Pokemon Go was released in July 2016.] I said we should put something up along the lines of Pokemon. So the first time I ever changed the sign, I changed it to: “RARE POKEMON INSIDE”. Everybody was kind of hesitant, but they let me put it up, and it went viral. I couldn’t believe the reaction from it. We had people waiting outside with their kids, assuming there was actually a Pokemon inside and asking if they could go in before the club opened.

It truly opened the door for the GM at the time: he saw the potential and he let me run with it. Ever since, they’ve let me have free range for whatever I want to do with the sign.

How did you break it to the children that there was not a Pokemon inside?

I kind of let the bouncers do that [laughs]. The GM would be there during the day and he would get people ringing the doorbell and saying, “I know my kid can’t come in when it’s club hours, but we were hoping to come in right now.” The GM would be like, “I’m pretty sure it’s a joke.” But he didn’t know anything about Pokemon Go—nor did I, realistically.

Every now and then I would come to work during that month and the bouncers would be like, “People are looking for your Pokemon.” And then I’d have to tell them, “I’m sorry. It’s a joke.” 

It might be time for a Kate Middleton sign.

[Laughs] I’m really excited for the NHL playoffs. I have poked fun at the Canucks over the years because they haven’t been great. Now they’re playing good, so I’m waiting for the playoffs to start so I can poke fun at whoever we’re playing. And then maybe poke fun at myself for making fun of them in the past—take back my previous jokes, or something to that effect. If they do well in the playoffs, I’m fully willing to apologize for poking fun for all those years.

How do you come up with all of your ideas?

Stuff hits me in the weirdest ways. I could be getting up to get a glass of water in the middle of the night or walking along the seawall; it might not even be a full joke, but something could just pop in my head where it’s even even a funny word or a punchline that doesn’t really have a joke on top of it. So I always just jot things down if I find them funny.

Or I’m trying to bank on current events. If something’s happening in the world that’s, as the owner always calls it, big news—whether it’s marijuana being legalized or Donald Trump running for president—we try to go with that. Other than that, I truly have a never-ending list in my phone. 

I only have about 40 characters, with spaces, to make a joke.

Forty characters is not a lot.

And for instance, a W—the actual letter is a lot wider than an I. So even when I’m thinking of stuff, I have to realize, “Yeah, I do have 40 characters, but I can’t necessarily necessarily write WWW-dot.” That would take up half of a line.

I’ve had friends be like, “Why don’t you put half on one side [of the marquee] and half on the other?” But I would hate the idea of someone just seeing half of it and not getting it. 

You’ve been at The Penthouse for a long time. What keeps you excited about the job?

It keeps my brain working in more of a way than just being a bartender in my day-to-day job. I joke with the owner Danny every now and then, like, “Hey, I’m tapped out. I think I’ve said everything there is to say about a strip club on a sign.”

I like the pressure a little bit; it keeps me on my toes.

The idea of not having anything, or having to admit that I’ve run out, terrifies me. [Editor’s note: aside from a few holiday-themed ones, Jackson has never repeated a marquee.]

If you ever leave, will you pass the torch to someone?

I could pass it on. I would love to see somebody do it, but who that person is, I couldn’t tell you. Hopefully me until it’s no longer an option. I’ll do my best to keep them coming until then. But if it came to a point where I couldn’t do them, I would love to see somebody carry it on. It would be a cool feeling to laugh at a sign that wasn’t mine.

This interview has been edited and condensed for clarity.