Whether playing to a boisterous crowd of hundreds in New York or to a more intimate crowd here on the Vineyard, deejay Josh Tucker knows how to show people a good time.

He deejays at Oak Bluff’s premier nightspot, the Lampost, where he’s been spinning records for going on 15 years. How has he earned that kind of longevity on the notoriously mercurial scene of disc jockeying? With care. “You have to observe the audience and watch how they’re responding to the song,” Mr. Tucker said. “When I was starting off, I saw a deejay playing Barenaked Ladies to a primarily New York crowd [here at the Lampost]. I just knew I could do better.”

Mr. Tucker explained the delicate balance of catering to the audience and introducing people to new music. “If it was up to me, I would play house music [new stuff] all the time. But on the Island a lot of people are into Top 40.” So after deriding the dearth of quality in viral sensation Teach Me How to Dougie, he proceeded to play the song on request. While the dance floor exploded, Mr. Tucker laughed at himself for caving to the demands of an anonymous birthday girl.

For Mr. Tucker, deejaying is not about dropping the latest songs on an unassuming audience, but instead giving them what they want to hear. “Ultimately, a deejay is someone who can keep a party going,” he said. Timing is key. Sure, Empire State of Mind, the iconic Jay-Z track, is played to death, but do you really care when Mr. Tucker plays the track at midnight on Saturday night and you’re on the stage in the club? You don’t. But that isn’t to say Mr. Tucker is incapable of throwing a mean curveball. Just when you are expecting another auto-tuned dud you’re tired of hearing, he’ll throw in some hip-hop classic like Gin and Juice by Dr. Dre and Snoop Dogg, or an obscure electronic track such as Illegal Beat by Magic Mushroom.

Mr. Tucker also likes to play Lil Wayne and LMFAO. But these fresh hits are tethered to deep cuts from the 1970s and 80s, such as The Stroke by Billy Squier.

His insider tips? “Never treat this like a job,” he warned, “because the moment it stops being fun you’re finished.”

Mr. Tucker favors catchy beats over memorable lyrics. “Everybody likes to sing along to a chorus once in awhile, but the beat is what will keep the audience going,” he said.

In Oak Bluffs, a stone’s toss from the Flying Horses carousel, the Lampost setting exudes old-fashioned, natural Island charm. Dockside, the fish are jumping. So are the folks on the dance floor at the Lampost, from graying baby boomers to millennial babes.

A bit wary at the beginning of the interview, Mr. Tucker opened up when asked what makes the music scene in the Vineyard unique. “Everything here is natural,” he said. “Homegrown. People actually use instruments instead of computers.”

He eschews mash-ups (a mash-up is a combination of two different songs, such as Tambourine Reckoning by the Hood Internet which samples both an Eve song and a Radiohead song), favoring traditional tunes that people know and love. “Mash-ups throw me off,” he said.

He acknowledges his forbears, giving thanks to people like Steve Mack as well as the Davies brothers for teaching him the intricacies of the spinning wax. Despite over 20 years of professional deejaying, Mr. Tucker still treats the art form as a hobby and not a job. He has two day jobs, selling real estate and driving a cab. He’s also a family man; he met his Canadian wife at the Lampost through a friend, and spent several years in Quebec living with her.

While he reminisces about playing to crowds of hundreds while getting started in New York in the late 1990s, these days he is focused on the family and often skips the after-party to return home. And he has big plans for the future, including several off-the-record projects. He allowed that he acquired a new software that allows him to mix and blend videos the same way a deejay mixes songs.

“I love music because it’s constantly evolving,” he said. That’s the same reason you might want to visit the Lampost: There’s always a new song, a new face or a new approach, couched in a familiar setting. Who knows? If your luck runs anything like Josh Tucker’s, you could meet the love of your life — right here at this venerable Oaks Bluff landmark.