Bartender Spotlight: William Pineapple Feels At Home in NYC

After stints in Dublin, Belfast and London, making drinks in the Big Apple still feels like top of the hill.

photo by Gabi Porter

“My uncle told me if I wanted to travel, people have to eat and people love to drink, so learn to be a chef or a bartender and you can get work anywhere in the world,” says the bartender known as William Pineapple, who in the past 3.5 years, most notably at Holiday Cocktail Lounge, has made the bustling drinks scene of New York City his home. He says this advice prompted him to start bartending at age 14 in his hometown of Werribee, Victoria in Australia at a local Italian restaurant where bartenders were also expected to make all the desserts. Since then he’s come a long way, and like many career bartenders with more than a decade behind the stick, is looking toward the next chapter, as well as ways to find a healthy mental and physical balance with what can be a stressful vocation.

These days, now that he has moved on from Holiday, that means a mix of bartender shifts and working with brands--work that is a culmination of his experience. Pineapple says he gravitated toward cocktail making from the get-go. “It was always cocktails for me, I can’t explain why but maybe it’s something about the art and the creative side of my life. I was a good musician but terrible at drawing.

Past gigs and bartending inspiration

After leaving Australia for Dublin, where in 2009 the drinks scene was just emerging, Pineapple went on to Belfast, eventually working under Jack McGarry at The Merchant, before heading to London. There he was introduced to the late, great Dick Bradsell while at the now closed Paramount Club. “He was an absolute gem, from the second I met him there was a mutual respect. I have no idea why he respected me, he had never met me and at the time I’d only been in London a few months but maybe that’s why we ended up so close. He was brilliant all the way to the end, no bullshit, just hospitality. I miss and think of him often.” Although Pineapple was working regular bartending shifts, if Bradsell needed a barback in a pinch, Pineapple was happy to oblige, no questions asked.

Finding balance

Up until landing in New York, the vagabond lifestyle didn’t allow for much of a cocktail book collection, but Pineapple says Gary Regan’s Joy of Mixology (now available in a newly revised edition) has been somewhat of a bible, and he often gifts it to new bartenders (who can now also access his Worldwide Bartender Database here). But one of the things no cocktail book has really delved into is the physical and mental stress of bartending full time. “There is a lot of pressure these days. Back when I started, everyone just wanted to make drinks for people,” says Pineapple. “There was no money in bartending, there was no fame. There wasn’t even a global completion to my knowledge. Then social media happened and boom, there changed my life and my industry forever.”

More pressure to be noticed means more after hours activities, being “on” in a down mood, and less regular meal times, sleep or workouts. “‘Balance’ is a word thrown around all the time in our industry but in my opinion balance is a personal thing. Everyone’s balance is different. I love sleeping late but recently I started working out again. It’s really changed the way I look at balance.” When working brand events, well-rounded meals can be tricky since eating times are so irregular, and defined by whatever’s available, whether it’s the not-so-nutritious party catering that typically comes in fried ball form or dependence on whatever a nearby food truck might be serving.

Americans drink (and order) differently

Between the five countries Pineapple has worked as a bartender, there are major differences in service and what people drink. In Australia, for example, he says it’s all about cranking out Espresso Martinis since it’s such a coffee culture. In London, gin is in, and the more intricate preparation, the better. In America (where he had to get used to people ordering drinks without saying “please” - just “I’ll have a…”), he is surprised by how often customers request their spirits neat, especially whiskey and tequila. “When I moved here full time, I did start drinking a lot more American whiskey. It’s just easier to get here and even the cheap stuff is absolutely delicious.”

However, he’s really a rum guy. “I was born in a town [near Bundaberg] where we have sugarcane, a distillery, a ginger beer and pineapples [hmmmm. Hence the nickname?]. I think maybe it was a birthright.” Pineapple admits he also could have learned it on the job. “Or maybe it’s that I worked at Trailer Happiness in London for around 3 years. One of which I was the GM. Trailer is like the home of tiki for Europe in my opinion.” It has a lot in common with Holiday in New York City. “It’s a great bar that has been through some rough times but it’s still there and still opening its doors every day.”

If you can make it there…

photo by Gabi Porter

Of his favorite NYC bars, Pineapple is more drawn to neighborhood hangs - Little Whiskey, 7B (a.k.a. Vazacs Horseshoe), Swift, Sweetwater Social, Subject. When he’s in the mood for a well made cocktail, he’ll venture to by Amor y Amargo, Attaboy, Bar Goto, Pegu Club and Dear Irving. He says that being in New York this long has changed the way he looks at service. “I feel I’m more relaxed with my guests.” Even with that softer approach, he says the energy of the Big Apple has honed his response time skills, “I have more tools to evaluate situation quicker.”

After 16 years of bartending, Pineapple still feels drawn to the big city. “I’m not done with New York yet.” Eventually, he’d love to have his own place if the circumstances allow, especially now that he has a better understanding of how the hours and activity can affect his wellbeing. In the end, he can see himself bartending for decades to come. “There’s an energy that’s almost sexual to making drinks. It’s alive. It’s creative.”

Welcome home.