Sailor Boy Penny Candy from Cracker Jack – And Cracker Jack!!

I’ve always looked at Cracker Jack as more of a snack food than a confectionery product, but it really is a confection.  Because of that, on it’s own it could be considered a legitimate topic for CollectingCandy.

Recently however, a wrapper surfaced from the early part of the 20th Century which provides a direct link between Cracker Jack and classic wrapped candies.  It’s one I never knew existed.

Produced by the Cracker Jack Company of Chicago, Sailor Boy penny candy was a wrapped treat sold in the 1930’s.  The wrapper features the classic Cracker Jack sailor boy mascot and dog, holding a box of Cracker Jacks.  Here’s the wrapper:

Cracker Jack Company – Sailor Boy candy wrapper – 1930’s

That Sailor Boy wrapper is a pretty great piece of confectionery history, because it firmly ties the world and history of Cracker Jack together with that of standard wrapped candy.

Even before this discovery I’d been interested in Cracker Jack packaging and picked up a number of interesting pieces over the years.  I’m going to take this opportunity to share a number of them today.  So let’s get to it.

First, a couple oddball pieces that diverged from the standard Cracker Jack formula.  This is a package for Cracker Jack Popping Corn:

Borden – Cracker Jack Popping Corn – file copy plastic pack – 1970’s

And here is the second version box design used for a 1980’s Cracker Jack branded cereal:

Ralston – Cracker Jack Cereal – free inside – bike spoke reflector – cereal box – 1985

And here’s the look of the cereal box from its initial release:

Cracker Jack cereal box design from 1984 – via Gregg Koenig

Now onto some actual Cracker Jack:

Borden – Cracker Jack foil box wrap – 1968

Borden – Cracker Jack – candied popcorn snack box wrap – late 1970’s

Borden – Cracker Jack – 1 box free – snack box foil wrap – 1970’s

Borden – Cracker Jack – Marvel Super Heroes toy surprize inside – box panel scans – 1979

In the 1980’s, Cracker Jack would get a run of nostalgic packaging, each one telling the story of the history of the brand:

Borden – Cracker Jack – Nostalgia package wrapper – Bear Postcard – late 1980’s

Borden – Cracker Jack – Nostalgia package wrapper – Bear Postcard alt – late 1980’s

Borden – Cracker Jack – Nostalgia package wrapper – Airplane Spotter alt – late 1980’s

There was also a short-lived flavor-extension for Cracker Jack that was released in the early 1990’s:

Borden – Cracker Jack Butter-Toffee – New Flavor – package wrapper – 1991

Borden – Cracker Jack Butter-Toffee – Nickelodeon game card – package wrapper – 1992

Borden continued to produce Cracker Jack with its classic design well into the 1990’s.

Borden – Cracker Jack – box wrapper – 1994

Borden – Cracker Jack – Looney Tunes prize inside – box wrapper – 1996

In late 1996, Borden would take their classic mascot illustration and give it a significant update with this look:

Borden – Cracker Jack box wrapper – New prize inside – 1996

Borden – Cracker Jack – Scooby Doo Prize Inside – box wrapper – 1997

In 1998, another major change for the Cracker Jack brand occurred when Frito-Lay took ownership of it, as you can see here:

Frito-Lay – Cracker Jack box wrapper – prize inside – 1998

Frito-Lay – Cracker Jack – snack package bag – Ploids coupon – 1998

Cracker Jack has been a part of the Frito-Lay family since 1998, and remains so today.

Frito-Lay had experimented around with some exotic flavor extensions like green apple flavored Cracker Jack, but I’ve not yet been able to track any of those down yet.  But when I do, I’ll come back and write about them here on the site.

So for today, that’s everything I’ve got to share on this wonderful confectionery classic.

See you next time!

About Jason Liebig

A New York City based writer, editor and sometimes actor. After spending much of the 1990′s in the comic book business helping tell the stories of Marvel Comics’ X-Men as series editor, he has since split his time between developing his own entertainment properties while still consulting and working on others. Having been described as “the Indiana Jones of lost and forgotten candy”, Jason is one of the country’s premier candy collectors and historians with his discoveries appearing in countless blogs, magazines, newspaper articles, and books. Always happy to share his knowledge and unique perspectives on this colorful part of our popular culture, Jason has consulted with New York’s Museum of Food and Drink and has also been a featured guest on Food Network’s Heavyweights, France’s M6 Capital, and New York’s My Google Profile+
This entry was posted in 1960's, 1970's, 1980's, 1990's, Boxed. Bookmark the permalink.

3 Responses to Sailor Boy Penny Candy from Cracker Jack – And Cracker Jack!!

  1. Dave B says:

    Have you seen the latest packaging for Caramel Cracker Jack? Its an old-style Jack-and-Bingo with a red Cracker Jack slash and Prize Inside in the blue circle on a plain brown background that even has subtle fake antiquing at the box edges.

    Nothing about it on the Fritolay website, so it aroused my curiosity.

    I’ll send a picture if you like.

    I’m a fan of the 1893 Chicago Exposition so Cracker Jack is naturally part of my world!

    Thanks for your site. Well done!

    Dave B

    • jasonliebig says:


      I HAVE seen the latest “retro” Cracker Jack packaging showing up. Always fun when they give us one of the classic designs!

  2. Ryan says:

    I have two of the Marvel cracker jack boxes sealed in a hard plastic case, wonder if there worth anything?

Leave a Reply

Your email address will not be published. Required fields are marked *