My Strangest Job: I Was as a Pirate Cigarette Girl

Probably the oddest job I’ve ever had was when I dressed-up like a pirate, strapped a tray of over-priced cigarettes, candy, and light-up toys to my shoulders, and sold them to drunk people in San Francisco bars.

It was early 2009. I’d just quit my nice corporate Costume Designer job in San Diego, so I could finish my bachelors degree. My goal was to switch my career to something more meaningful and less soul-crushing. So I’d traveled back up north to Oakland, to finish my diploma at the college I’d started it at 11 years prior.
Of course, this was also when the economy had just tanked into a recession.

When I got to Oakland, I applied for flexible jobs I could work while in school full-time. I applied to all sorts of things. I had tons of retail and food service experience, it should have been a cinch. But, given the economy, NO ONE was hiring.
I went from a salaried job to having an ice cream shop not even call me back. The financial cushion I’d worked to save was running out, made worse by the fact that when I gave 3 weeks notice to my design job they let me go on the spot. (Lesson: NEVER believe a company who says their employees are “like family”. You’re not. You’re just a cog in their machine.) After getting no bites for months, shit was getting desperate. My credit cards could only keep me afloat for so long.

Then I saw an ad on Craigslist. A company called Peachy’s Puffs was hiring. They wanted girls to be the classic “cigarette girl”, to dress up in costumes and work parties and bars. Heck yes, I thought. I am a sucker for retro anything, and I love dressing in costume, so I was sold.

I applied, interviewed, and got the job. I breathed a huge sigh of relief.

The job turned out to be… interesting, to say the least. The company’s history was great, it had been started by one enterprising young woman in 1988 who called herself Peachy D’Ambrosio. She’d sold the company by the time I worked there, but they retained the name Peachy’s Puffs.

Their website looked pretty slick and had glamorous photos of the girls.
What I found in reality was not glamorous in the least.

Here’s a little snippet of what it was like to be a Peachy’s Puff in 2009:

It was 8pm on a Friday night and after being in classes all day, I drove out to San Francisco and parked my car near the Peachy’s Puffs office. I punched in the door code, then descended the stairs to the basement level office space. The office was also our dressing room, and it was a sad, run-down, florescent lights and scuffed linoleum floor affair. A funky old vending machine dispensed soda and beer.
I set my huge tote bag of costumes and supplies down at one of the dressing stations, got out my curling iron, and plugged it in. One girl was already there, she was brand new, and this was her first night. I said hi, and she meekly replied, shyly hunched over, applying her eyeliner. I knew she wouldn’t last at this job past tonight. This gig was not for the shy or meek. Poor dear.

I shimmied on my pirate outfit, it was a ice blue and white lacey dress meant for a sexy Marie Antionette costume, but I paired it with a pirate hat topped with a huge, jaunty blue feather, fishnets, and knee high black Fluevog boots. I started to curl my hair, and other Puffs rolled in soon after. A brassy new gal with a Jersey accent sat down next to me. Her name was Cindy, she’d just moved from the East Coast, and she was just working this job until she could find a waitressing gig. Next to her was a petite gay boy named Alexander. He wore a perfectly fitted bell boy costume with super short shorts, and he only worked the Castro neighborhood (the “gay” neighborhood of San Francisco.) I’m sure he made a ton of money there.

Cypress as a Cigarette Girl Pirate. This is a photo from my first night, when I wore one of the costumes from the staff closet.
Cypress as a Cigarette Girl Pirate. This is a photo from my first night, when I wore one of the costumes from the staff closet. It was soon replaced by my own costume.

The rest of us were assigned our routes, and I got North Beach, again. More senior girls got first dibs on the best routes, and while you could make money in North Beach, it was also super sketchy due to all of the strip clubs in the area. Cindy and the meek girl were also on my route. After finishing with hair and make-up, we counted in the items in our trays, and our driver, Matt, told us it was time to get going.

We drove away in Matt’s 90’s sedan that reeked of weed, while he blasted metal through the stereo. He dropped me off first, on a street lined with bars. He wrote down on scratch paper the names of the bars I was to go to, and what corner I’d meet him on at 10:15. I had his cell number plugged in my phone just in case. Then he drove away to drop the other girls off at their sections.

I took a deep breath, adjusted my heavy tray, fixing a glow stick that had fallen over and turning my electric pink “tips” sign outward, and walked into my first bar. It was pretty packed for so early in the night. As I did with every bar, I acted like the cartoon character of a cigarette girl, bubbly and bright and cutesy cute. If you know me, you know how difficult this was- I hate selling things, and I hate being fake. But I had to fake it to do the job, so the little voice in my head yelled “WORK IT, GIRL!” and work it I did. I talked to everyone in the bar that I could, charming the folks who looked hungrily at my M&Ms, dodging snarky looks from ladies who were there with their boyfriends, and coyly cutting short conversations with men who were just flirting and wouldn’t buy a thing. Most people were nice or neutral to me, but some just gave me disgusted looks. I knew wearing a skimpy outfit and selling crap in a bar made some people look down on me. I tried to blow it off and keep moving. With all that work, I sold only one pack of over-priced peanuts. So on to the next bar I went.

I efficiently worked my way through my list of bars, sold a decent amount of items, but it was still early, people would buy more later on when they were drunk. I stood patiently on the ending corner for my ride. Matt pulled up to the curb, and I jumped inside. We picked-up the other girls on their corners and off we went to our next routes.

This string of bars was a little more spread out, and a bit confusing because I wasn’t familiar with the neighborhood. The first bar was a two story monolith I’d never seen before. It was frequented almost exclusively by transgender women and the fellas that love them. It was a bit slow, but I sold some chocolate bars to a couple of gorgeous ladies who begged their “daddies” to buy them treats.
The bar after that was a rocker dive, and the bartender exchanged pirate jokes with me, then gave me a free shot because he knew “how hard my job was”. Then I walked down the bustling main drag in North Beach, and things were really beginning to hop. People were filing in and out of bars and strip joints flashed their neon signs.

At a tiki-themed bar, I took a brief break to dance to “Groove is in the Heart” while wearing my tray. Afterwards a drunk jackass grabbed one of my candy bars and threw it across the room. I panicked, as each over-priced thing on my tray would be charged to me if it went missing. Luckily I found it on the ground, and it looked fine, so back on my tray it went.

At the next bar, a gorgeous sit-down place with stained glass windows and a spiral staircase, a darling Irish guy, on vacation I’m sure, chatted me up right when I walked in. He had that starry-eyed look when he saw me, and I practically melted when he said in his fabulous accent that I “looked like the girls back home.” He tried to sweet talk me into hanging out with him all night. And I almost threw down my tray then and there… but, no. I had a boyfriend and I was working. Time to move on.

Walking to the next location, I took a wrong turn for a moment, accidentally walking down a dark street, when I realized I was alone there, I panicked and started to briskly walk back. A guy in a car also spotted me, and like a perfect predator immediately pulled to the curb and tried to call me over. I walked faster, and made it back to the populated street. I took a big breath to calm down my thumping heart.

A group of guys standing outside the next bar started to chat me up when I approached. At first I wasn’t sure if they’d buy something so I entertained them.

“What’s your name?” one of them asked.

“Lulu the Merciless.” I said in a Betty Boop voice.

“No, what’s your real name.”

“That is my real name.” Coy smile.

I saw their eyes dart right behind me, and I realized one of their buddies had snuck behind me, lifted my skirt, and taken a cell phone picture of my butt (I wore shorts underneath, thank god.)
I told them all they were uncouth and stormed away to my meet-up location.
I noticed my hands were shaking a bit. Breathe. I needed a drink.

The next route was a simple one, as the two clubs were huge and packed with people. The first was in an industrial district, booming with house music, and I sold a few things. This was the perfect time of night to sell my $10 packs of cigarettes. People’s laziness and drunken nic fits had overrided their outrage at the price.

At my last stop, there was a line to get in. The bouncer lifted the velvet rope for me and let me inside. The Hip Hop blared in this sparkly, posh, multi-room dance club. I really wanted to make some more sales at this place, this was go time. But as I walked around I quickly got the hint that I was invisible here, who knows why, maybe these people didn’t like pirates. Barely anyone would even look at me, and no one would speak to me. Still hopeful, I walked through all the rooms, then just sat, dejected at the bar. I ordered a whiskey sour and got off my throbbing feet for a minute. What a bust, and this is the prime time of night for people to buy things. Damn.

Matt picked me up outside at 2am and we drove back to the office. Cindy was chatty as ever, bragging about her score of selling 5 cigars AND the vibrating penis-shaped lighter to one group of people. The meek girl was crumpled against the corner of the back seat, sunk into herself, eyes glazed over. Yep, that one was done for.

At the office, we deliriously counted our trays back in, and our percentage of the revenue was calculated. We got some measly cut of it, around 25% at the most. The office manager handed me my $65. I sighed. She told me that was actually really good, most people made less.

Looking around at my co-workers in their ragged, 2:30am haze, I realized this job was for people on the precipice. It was for people in between something else, or, for those who felt they were running out of options. And it was difficult, emotionally and physically taxing, and disheartening for most. As most jobs that have to do with bars, nightlife, exploitation, and low pay, it felt like we were teetering above a dark abyss of desperation. I had my toes firmly on the ledge, but I could see how it might push a younger or more delicate person over.

I changed out of my pirate costume and said my goodbyes to the motley crew of Puffs still packing up their gear. I slumped back into my car, my back and feet were beyond sore, and I made the groggy drive back to Oakland at 3am, not much money in my pocket, but at least it was something.

Soon after I found a stable retail job, blessed be. But from that day forward, whenever I see a cigarette girl in a bar, I always buy something from her and give her a tip.


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