In 1992, Leigh Henry tried to sell Pete Aitkin a karaoke jukebox.
The Black Duck owner said no.
But he asked Leigh — a 1968 Staples High School grad, with a long and varied music career — if he’d host a karaoke show instead.
Leigh said yes.
Which is why — a quarter century later — the Duck is celebrating 25 years as Westport’s go-to karaoke restaurant/bar.
Leigh is a storied figure in Fairfield County. While still a Staples student, his band — Mandrake Root — opened for the Doors, and Sly and the Family Stone.
Leigh spent 15 years organizing shows, then booked music for clubs and private events. For 3 decades his band Celebration has played weddings and parties. He’s the vocalist in another group — the Leigh Henry Band — and also DJs.
In the early ’90s Leigh was selling karaoke machines, like those in Asia where people pay to sing. But Aitkin thought that if the Duck sponsored karaoke, there should be a host.
Before the opening show, Leigh wondered if anyone would come. He still recalls the first person — a woman named Maureen. She sang “Leaving on a Jet Plane.”
At that moment, Black Duck karaoke took off.
Black Duck karaoke, in the early days.
“Tuesday nights were wall to wall,” Leigh says. He added Mondays too, for 23 years.
Leigh’s karaoke fans like older music — classics. Not a lot of hip hop. The 3 all-time favorites, Leigh thinks, are “Livin’ on a Prayer,” “Don’t Stop Believing” and “Sweet Caroline.”
The Duck itself plays a huge role in Tuesday karaoke’s long success.
“The vibe is completely comfortable,” Leigh notes. “It’s a great equalizer. There are no pretensions. Bikers, tech guys, yuppies — everyone leaves their attitude at the door, and mucks in together.”
Just another Tuesday at the Duck.
The layout helps too. “There’s a bar where people sit safely. They can engage or not,” Leigh observes. “You can sit at tables. The place is small enough to be intimate, but large enough so there’s a lot of energy.”
Mike “Wolfie” Connors — the popular bartender from Day 1 to 2015 — also played a big role, Leigh says.
Five years ago, the Duck celebrated 20 years of karaoke with a party — and a fundraiser for the American Cancer Society.
Westport’s favorite karaoke spot.
For this 25th, Leigh upped the ante.
Tuesday, June 13 and 20 are “Applause for the Cause” nights. They’re like Relays for Life — except people sing to raise money, rather than walk.
The 1st night is “Only a Pay-Per-Tune”: donate $25 to sing a song.
The 2nd evening is a “Sing-a-thon.” Team leaders who raise $500 earn a 3-tune mini-set. They can perform themselves, or offer their slot to friends.
Leigh’s goal is $10,000 for the American Cancer Society.
Good times never seemed so good.
(To become a team leader, sign up for a song or make a contribution, click here. For more information, email email@example.com)
Brett is one of many Black Duck karaoke stars.