Jackopierce: “Young & Free”

In 1985, almost 4,000 people crowded into Longshore. They were excited to hear Hall & Oates. The duo — known for smash hits like “She’s Gone,” “Rich Girl” and “Private Eyes” — were about to perform, as part of Westport’s 150th anniversary celebration.

Except no one told Hall & Oates. A local nanny — claiming to represent the group — scammed the town.

Fortunately, the crowd got a bit of music. A local band called Pseudo Blue stepped on stage. It was their first paying gig.

Not bad for a bunch of Staples High School students.

Cary Pierce, in the Staples HIgh School 1987 yearbook.

Cary Pierce remembers that day well. He and his good friend — fellow rising junior Doug Dryburgh — were in Pseudo Blue.

The band did not last beyond graduation. But in his first year of college, Cary met Jack O’Neill. They formed their own duo: Jackopierce.

They shared stages with Dave Matthews, Counting Crows, Sheryl Crow, Lyle Lovett, Matchbox Twenty and Widespread Panic. They performed in clubs and at colleges across America — and before 500,000 people at the Texas Motor Speedway.

Thirty years later, they’re still going strong. Jackopierce has just released a new single. “Young & Free (The 80s Song)” is an homage to growing up listening to Joan Jett, Joe Jackson, General Pub, Pretenders and Book of Love.

In fact, the song mentions 85 bands and singers — Flock, Till Tuesday, Talking Heads, Tears for Fears, Big Country, Devo, Smithereens. You name it, they’re there.

But it’s the first line that is of particular interest to “06880.”

Cary sings:

I remember lying on my bed
Borrowed guitar across my chest
Mean streets Westport, Connecticut
The New Wave running through my head

My sister dated drummer boy
Parents’ basement we made some noise
The Call, the stage, the lights, the girls
Who doesn’t want to rule the world?

Cary Pierce today. He has not changed much.

“Young and Free” channels Cary’s youth. For years, he and Jack have joked about growing up on the “mean” suburban streets. (Specifically Greens Farms, Cary notes.)

This might be the first time our town has been mentioned in a song since Pearl Bailey’s “I Caught Her in the Kitchen Playing Westport.”

Its influence on Cary is strong. It was here that he learned to play guitar and keyboard. At Staples, he and Dryburgh started an annual Band Bash that grew to include a dozen groups.

He listened to New Wave bands on WLIR. He watched the new sensation — MTV videos — at his friend Matt McClellan’s house.

Cary figured he’d go to a small New England college like Wesleyan. But, he says, “my guidance counselor had a better handle on my grades.” She suggested Southern Methodist University.

Cary had never been to Texas. But he fell in love with the Dallas school, and applied early decision. “It was the best decision I ever made,” he says.

He was involved in theater program and journalism. But his time there was most defined by his collaboration with Jack O’Neill, who he met in 1988, on one of his first days on campus.

They quickly learned covers of songs by the Eagles, Jimmy Buffett, John Denver and James Taylor. They played fraternity and sorority dances, then branched out to colleges across Texas and Oklahoma.

Fans who heard them told friends and siblings. Soon Jackopierce was driving 9 hours to play at the University of Kansas, and flying to gigs at the University of Michigan. They’d sell 100 CDs, which paid for the trip.

Jackopierce, on stage.

Jackopierce’s first record — independently done — sold 45,000 copies. An attorney in Nashville got them a contract.

The label connected them with T Bone Burnett. The legendary producer (Los Lobos, Gregg Allman, Roy Orbison) helped move them from “earnest frat boys” to appearances on Rosie O’Donnell and Conan O’Brien, and stories in Rolling Stone.

Their first album with Burnett sold 100,000.

So did the second. Not seeing any growth, Cary says, “the label yawned.”

Management talked Jackopierce into a farewell tour. Jack moved to New York. He and Cary did not speak for 5 years.

“It was my first divorce,” Cary says. “I didn’t see it coming. It was painful. I learned a lot.”

Five years later, he went through an actual divorce. He felt “completely broken.” But then — providentially — Jackopierce reunited.

That was 2002. They’ve been together ever since.

Jack O’Neill (left) and Cary Pierce.

Jackopierce has devoted — even rabid — fans. They’re all across the country. Most don’t know Westport.

But Cary does.

“I have no idea if people there will be offended” by the winking “mean streets” reference, he says. He hopes not. He still loves the town.

“I had no idea what I had back then. It’s an incredibly beautiful, very privileged place. I had an old 14-foot Boston Whaler. I’d go from Longshore to Peter’s Bridge, get a sandwich, then head to Cockenoe. It was la la land.”

“Young & Free” has been released in “a strange time,” Cary says. COVID has canceled live shows. He and Jack are marketing it the old-fashioned way: grassroots, by themselves.

They’ve contacted all 85 artists mentioned in the song: Depeche Mode, Billy Bragg, Hooters, Toto, Blondie, Men at Work…

Now all of Westport can enjoy Cary Pierce’s musical trip down memory lane too.

“Young and Free (The 80’s Song) is available on Spotify, Apple Music, YouTube, Pandora and Amazon Music. Click here for links.)

12 responses to “Jackopierce: “Young & Free”

  1. Ah yes, the Mean Streets of Westport. Reminds me of driving through Westport with my son when Bruce’s “My Hometown” comes on. I like to tousle his hair and substitute lyrics like “closing down the textile mill” with things like “shuttering hedge funds” and “closing down the marketing agency.” He puts up with me.

  2. Wow, that post just brought me right back to high school! Although Cary and I did not know each other, I remember him. (I was class of ’88). I remember the Hall & Oats debacle and Pseudo Blue saving the day. I was at Band Bash and several other things that Cary was involved in. I had no idea he had gone on to such a great career. Congratulations Cary!!!
    I no longer live in Westport but I’m so glad I grew up there when I did. I, too, joke around that I grew up in the ‘hood. People just laugh and roll their eyes.
    And thanks for the memories, Dan. That was a great way to start a dreary day!

  3. Jennie G Pickering

    I was 10 at that confusing Hall + Oats event….you could cut the anticipation, and confusion, with a knife! Just wonder why there haven’t been outdoor concerts like Hall + Oats etc at Longshore since then…random

  4. Well done; very catchy tune.

    And thanks for the post. I learned something new about Westport’s music history.

  5. Michele (Coppola) Mottola

    This is amazing, brings me right back to the mean streets of Westport. Congratulations Cary, so happy for your success. Love the song.

  6. I had no idea the “Pierce” in Jackopierce had Westport ties. I was still climbing on the canons at Compo when he was at Staples, but, I love hearing these stories.

    Thanks to Dan for bringing us these stories we’d otherwise never hear.

  7. Roseann Spengler

    Good story, Dan. And, good memories. Thanks!!

  8. Fountains of Wayne, in “Laser Show,” on their 1999 album Utopia Parkway, includes the line “They come from Bridgeport, Westport, Darien, down to the Hayden Planetarium”.

  9. Peter Gambaccini

    I have one of the Jackopierce CDs produced by T Bone Burnett and it’s still on pretty heavy rotation in my home. Like others here, I had no idea Pierce was from Westport. You live and learn.

  10. Actually, Westport did make it into a rather famous song between Pearl Baily and Cary. In 1970 REO Speedwagon recorded their first album in Bridgeport, and the lyrics tell the story:

    “We flew into town on Sunday
    Had to find a place by Monday
    Tried Bridgeport, tried Westport
    ‘Til we found a place that we thought would do
    157 Riverside Avenue

    Saugatuck River’s flowin’
    Mother nature’s colors were showin’
    So cold, so rainy, we couldn’t help feelin’ blue
    Not enough time, too many things to do
    So we just sat back and played some

    Well we met a young girl on Main Street….”

    and so on….
    They’ve sung it in concert forever, one of their trademarks, and probably would do it now if they were touring.

    Next time you drive up Riverside, take a look across the street from the school…#157. (It’s a new house, the old shaggy one REO rented is in a landfill)

  11. Diana B Pils Marino

    Great article. I loved the link to the song. I was at Longshore for Hall & Oats. I brought several work friends from Xerox Corp and we got hornswaggled … but I never knew the backstory. Thank you! Jackopierce is great!!

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