Tag Archives: Staples High School yearbook

Friday Flashback #512

Posted on July 17, 2026 | 9 comments

Printed high school yearbooks are forever.

Video yearbooks are not.

Briefly the rage in the 1980s and ’90s, the concept faded quickly once the cutting-edge technology became yesterday’s news.

And then unusable.

But whether your video yearbook is gathering dust somewhere (and you long ago tossed your VCR machine to play it), or whether you never bought one — or if you were not in Westport (or even alive) when these relics were made, but would love to see what Staples was like, back in the day: You’re in luck!

Staples grad Nick Wiener found 5 video yearbooks on YouTube. They’re from 1987, 1988, 1991, 1995 and 1997.

The picture and sound quality isn’t great. But that’s not the point.

Three and 4 decades after they were filmed, edited and distributed — and soon thereafter, forgotten — they live on.

Click below, and relive the glory days: of Staples High School, and video yearbooks.

The 1997 video yearbook cannot be linked directly. But you can click here to see.

Go Wreckers!

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9 Comments

Posted in Friday Flashback, Staples HS

Tagged Staples High School yearbook

Unsung Hero #422

Posted on February 18, 2026 | 6 comments

Stephanie Mastocciolo writes:

When Staples High School said that the deadline to submit senior baby pictures to the yearbook was the next day, I said to myself, “I have hundreds!”

Then I read the specifications of what and how to submit, and felt lost.

Of course I had plenty of recent ready-to-download-and-send photos of my daughter’s toddler and teenage years. But I remembered that all of our actual baby pictures from 2008 are stored on CD-ROMs.

Remember these?

So I turned to the younger generation: my children. My puzzled and confused high schooler and middle-schooler) asked, “CD what?!” They could not help.

Having recently moved to a new home within Westport, our old desktop computer was still in a box somewhere.

We all use laptops. None has an external CD drive.

The deadline was near. All I had was a CD, and some physical photos in family albums. The instructions specified “no low resolution pictures of a picture.”

I thought the Westport Library must have a CD drive, where I could upload my picture to send to the yearbook.

I drove over with an hour until deadline, and headed to the computers. All I saw were USB ports.

I walked over to the reference department. Michelle Fleisher listened to my problem, then sprang into action.

Help!

She didn’t know if she could help. But she called to find answers.

Within minutes, a man appeared — with an external CD drive. He said I could sign it out, to take home.

Michelle insisted we try it right there, and connected the device. She walked me through each step.

I am not the most technologically savvy person. But I learned something new.

I want to thank Michelle. She not only answered a simple question; she also offered patience, a friendly attitude, and a willingness to assist, teach and guide me.

She went above and beyond. I submitted my child’s baby photo in the correct format, on time — and was even able to store all my images to an updated digital folder, for future use.

Saved from a CD — and submitted on time.

Thank you, Michelle. The Westport Library is lucky to have you!

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6 Comments

Posted in Library, Staples HS, technology, Unsung Heroes

Tagged CD-ROM, Staples High School yearbook, Stephanie Mastocciolo

Friday Flashback #165

Posted on October 25, 2019 | 10 comments

Today is Staples High School’s Homecoming. There’s an afternoon pep rally; all fall teams will be introduced. There’s a football game at night. The stands will be full. Captains of all sports are announced at halftime.

That’s it. No dance. No Homecoming king or queen. No

It’s been that way for a couple of decades. Dances are out of favor. King and queen are not cool. Floats got the kibosh years ago, because the heavy trucks that pulled them damaged the track.

Several years ago, when lights were added to the football field, the Saturday afternoon event moved to Friday night.

So here’s a look back, 50 years ago. In 1969, Leslie Wilker was Homecoming Queen…

… and here’s a typical float. Each class built one (somehow, the seniors always won).

Floats did not always have a G-rated theme. In 1984 — when the drinking age in Connecticut was 18 — the senior class celebrated Homecoming with a bottle, and this slogan:

That decade-plus of 18-year-old drinking made Staples a different place. In 1982, administrators gave a special gift to all seniors, at the prom: a beer mug.