The original, invented by Richard LaMotta (1942–2010) in New York City, was made up of vanilla ice cream sandwiched by two chocolate chip cookies with the sides rolled in chocolate chips which stick to the ice cream.
While ice cream sandwiches have been sold in New York City since the 1890s, Richard LaMotta created Chipwich in 1981. A guerrilla marketing campaign, in which he trained and enlisted sixty street cart vendors (mostly students) to sell them on the streets of New York City for a dollar each, established Chipwich as a successful brand. 
As an independent, the company struggled to find capital to expand. In 1984, burdened with heavy debt, Chipwich sought Chapter 11 bankruptcy protection. By 1987, co-founders Metzger and LaMotta had reorganised the company and obtained a $1 million investment from Swedish holding company Hexagon AB, which guaranteed loans and licensed its products. In 1992, the company was back in Chapter 11 bankruptcy after incurring a $1.4 million loss on sales of $4.8 million; an accounting scandal involving inventory overstatements at Peltz Food, a subsidiary headed by Mr. Robert Peltz, were at the root of much of the problem.
CoolBrands International bought Chipwich in 2002, becoming North America's third-largest ice cream vendor. Due to a series of financial difficulties which began with the loss of its Weight Watchers/Smart Ones frozen food licence in 2004, CoolBrands sold Chipwich, Eskimo Pie and Real Fruit to the Dreyer's division of Nestlé in 2007 as part of a larger divestiture of core assets which left the company as little more than a publicly listed empty shell.
The US trademark was abandoned; "Retrobrands USA LLC" with a long pattern of trademarking once-famous but abandoned names (like Ken-L Ration pet food, Hai Karate aftershave, Tegrin dandruff shampoo, Puss N Boots cat food, Tender Vittles cat food and Sani-Flush toilet cleaner) has claimed the mark. As of July 2014[update] "Chipwich Gelato" pint-size container of kosher Italian ice cream manufactured by Gelato Petrini is now available in NYC. through Marina Ice Cream, which has also re-launched the Original 5 oz CHIPWICH novelty brand both in Vanilla and Chocolate. It is currently sold in NYC with plans for all USA and Canada distribution.,
- The original brand is defunct. Chocolate Chipwiches by Susan Whetzel is one example of a chipwich recipe.
- "Dividends: War of the Chocolate Chips". TIME magazine. 1981-09-28. Retrieved 2014-07-28.
- Raisfeld, Robin (2006-08-17). "Our Ice-Cream Sandwich Taste Test". New York Magazine. Retrieved 2014-07-28.
- "COMPANY NEWS; Problems at Chipwich Unit Result in Chapter 11 Filing". New York Times. 1992-08-04. Retrieved 2014-07-28.
- "Passing the Hat...Again". Inc. Magazine. 1990-09-01. Retrieved 2014-07-28.
- "CoolBrands sells Eskimo Pie, Chipwich brands to Dreyer's". CBC News. 2007-01-24. Retrieved 2014-07-28.
- CoolBrands press release announcing sale of Chipwich to Dreyer's
- SCOOPS2U Ice Cream Catering Company's truck uses "chipwich" as a generic term for ice cream sandwiched between cookies
- "RetroBrands USA LLC, "Bringing back American iconic legacy brands to the marketplace"". Retrobrands.net. Retrieved 2014-07-28.
- Press Release: Iconic Chipwich Ice Cream Brand Launches Italian Gelato Pints in NYC
- "Marina Ice Cream Corp". Retrieved 2014-07-28.