1

$125 million for a Grade-school math error

Image: Aaron Lefler

Imagine losing a hugely expensive spacecraft due to a simple mix-up between English and metric measurements . That is exactly what happened to NASA in 1999 when a Mars orbiter designed by Lockheed Martin was lost in space.

The confusion caused a malfunction on the $125 million craft, resulting in the probe’s loss. Although it was unusual for Lockheed to use English measurements for a NASA design (since NASA had stipulated using metric measurements for many years), there were still several instances where the error should have been caught but wasn’t.

2

Toys ‘R’ Us blunder

Image: Taylor Heery

If you think an action figure of a drug dealer isn’t the best idea for a toy store , you’re not alone. Yet, for some reason, Toys "R" Us decided otherwise in October 2014, possibly hoping to cash in on the massive success of the Breaking Bad TV series.

Unsurprisingly, the giant toy retailer was forced to pull from its shelves four collectible dolls based on characters from the AMC hit show, each doll featuring a detachable sack of cash and a bag of meth.

3

Apple Maps' rocky beginnings

Image: CardMapr.nl

When Apple decided to launch its own map application on iOS devices after a conflict with Google in 2012, users quickly realized that the Apple app was not nearly as launch-ready as it should have been .

Locations were mislabeled, roads were missing, and it occasionally steered people in entirely the wrong direction. The problem was eventually, though largely, resolved, but it was an embarrassing misstep for a company known for never launching a product before it was as near-perfect as possible.

4

Bank of America debit card fee

Image: Ali Mkumbwa

Back in 2011, when the backlash against the banking industry had not yet reached its boiling point, Bank of America announced it would charge customers $5 per month to use their debit cards .

It was a bad business decision. More than 300,000 people signed an online petition, and Fox Business Network’s Gerri Willis cut up her debit card on air. The bank pointed to federal regulations as the reason for the charge but ultimately capitulated to consumer demand after a month before the fees went into effect.

5

$33 airline tickets from Toronto to Cyprus

Image: Miguel Ángel Sanz

If buying a business class ticket regularly priced at $2,558 for just $33 sounds too good to be true, it probably is. Except in 2006, when an Alitalia employee accidentally forgot to input two extra zeros when pricing business-class tickets from Toronto to Cyprus.

Due to the exchange rate on that day and the blunder, hundreds of buyers managed to snag fares for just $33. The airline honored those deals, accepting the heavily discounted price for the 509 people who purchased tickets before the error was detected.

6

A $70 million comma

Image: Nattipat Vesvarute

As the folks at NASA and Alitalia have shown us, small errors can lead to costly mistakes. The following blunder comes courtesy of Lockheed Martin , which issued a contract to a customer with a missing comma in the sale price .

The astute customer held the aerospace company to the contract, costing Lockheed Martin $70 million for a C-130J Hercules aircraft in June 1999.

7

Sears misses the ship

Image: Estefania Cortes

A retail giant that faced a situation similar to the one Kodak faced—embrace the new and unknown or cling to the old, successful recipe—Sears sold everything from socks to tires via mail order, shipping across the U.S.

Choosing to stick with the old method, the company ended its catalog and delivery business in 1993 . In 1994, Amazon was founded , filling the business void that Sears had just created. The rest is history.

8

Passing on Microsoft

Image: Jaime Marrero

$60 million might seem like a lot of money to us regular folks, but for someone with very deep pockets like Texas businessman and two-time U.S. presidential candidate Ross Perot, it wasn’t all that much.

In 1979, he was offered the chance to buy Microsoft for that sum. However, his final offer to the tech company was just $15 million, and as a result, the Texan missed out on the opportunity to own what would become one of the biggest companies in the world .

9

Blackberry sticks with the old

Image: Thai Nguyen

Another case of a brand sticking with the old instead of embracing the new, BlackBerry was all the rage at the start of the 21st century— until Steve Jobs came along with the Apple iPhone .

While BlackBerry Messenger was extremely popular, with over 80 million users worldwide, the device lacked the new touchscreen functionality and sleek design of the Apple product. From being a market leader, BlackBerry’s market share plummeted to 0.2% by 2016.

10

RadioShack’s downfall

Image: Jelleke Vanooteghem

Not so long ago, RadioShack was a familiar presence on the streets and the go-to place for buying batteries and electronics. But it was that same brick-and-mortar presence, coupled with a reluctance to embrace e-commerce , that ultimately led to its demise .

Eventually, poor profit margins on what they could sell, combined with a loan they couldn’t repay, brought down what was once the go-to place for electronics.

1

Blockbuster

During the 1980s and 1990s, Friday night often meant one thing for American families: a trip to Blockbuster. Browsing the aisles for a movie, debating what to watch, and grabbing popcorn at the counter became a weekly routine. But nothing lasts forever.

Born in 1985, Blockbuster conquered the massive home-video market with thousands of stores by the late 1990s and early 2000s, catering to families with at-home VCRs. Then technology changed everything. First came DVD-by-mail services like Netflix, followed by streaming, which left Blockbuster struggling. Late fees and inconvenience only pushed more customers away. The company filed for bankruptcy in 2010. Today, just one official store remains in Bend, Oregon, where visitors still stop by for a dose of the video-store era.

2

Kodak

Back in the day, almost every vacation, birthday, wedding, or holiday gathering seemed to include a Kodak camera, or at least a roll of Kodak film. Founded in 1881, Kodak helped keep the moments that filled family photo albums for generations.

From the 1960s through the 1990s, Kodak dominated the world of film and photography. But that success also made the company slow to accept that technology was changing. Ironically, Kodak helped invent one of the first digital cameras in 1975, yet it hesitated to embrace the future. By the 1990s and 2000s, digital cameras (and later camera phones) quickly replaced traditional film. In 2012, the company declared bankruptcy.

3

Pan Am

Long before flying became an everyday experience, Pan American World Airways, better known as Pan Am, was already carrying Americans across the world. It was founded in 1927, and during the 1960s and 1970s, the airline became a symbol of glamorous air travel.

Its famous blue globe logo was instantly recognizable, even to those who rarely flew. But by the late 1970s, rising competition, fuel costs, and financial troubles began weakening the company. After years of mounting losses and debt, Pan Am shut down in 1991. Even so, its fame was such that even today, more than 30 years later, we still remember it.

4

Woolworth’s

Before Woolworth's made the "five-and-dime" famous, shopping in America looked very different. For decades, Americans visited Woolworth’s for everything from toys and school supplies to household goods and everyday essentials. By the 1960s, the brand had become a familiar part of American life.

Created in 1879 by Frank Winfield Woolworth, the chain grew into one of the country’s largest retailers. But in the 1970s, malls and discount giants like Walmart changed the way Americans shopped, and Woolworth struggled to keep up. By the 1980s, the iconic chain was slowly disappearing. Most stores closed during the 1990s, and the Woolworth retail chain officially ended in 1997.

5

Circuit City

Testing giant stereo systems, browsing rows of CDs and video games, and shopping for the newest TV were all part of the experience at Circuit City, once one of America’s biggest electronics chains.

Founded in 1949 by Samuel S. Wurtzel in Richmond, Virginia, as "Wards Company," the retailer adopted the Circuit City name in 1984. During the 1980s, 1990s, and early 2000s, it became the go-to place for Americans buying a TV, stereo, computer, or any electronic device. But like many companies on this list, Circuit City struggled as shopping habits changed and online stores became more convenient. A controversial 2007 decision to lay off thousands of experienced employees further hurt the company’s reputation. Circuit City couldn’t survive mounting losses and closed all remaining stores in 2009.

6

Borders

Remember Borders? Born in 1971, its huge stores, filled with books, music, magazines, and cozy reading spaces, invited customers to spend entire afternoons there.

During the 1990s and early 2000s, the rise of large shopping malls actually helped Borders thrive, turning its bookstores into popular destinations inside malls across the US. But eventually, the company ran into a challenge it couldn’t overcome: online shopping and digital reading. Competitors like Amazon surged ahead, while Borders struggled to adapt and made costly business decisions, including outsourcing its online sales to Amazon for years. The company collapsed financially in 2011 and soon closed all remaining stores.

7

Bugle Boy

In the late 1980s and early 1990s, teenage fashion became almost synonymous with Bugle Boy. Famous across the country for its casual jeans and memorable TV commercials, the brand became a major part of American mall culture and was sold in department stores nationwide.

But fashion never stands still, and brands have to constantly adapt to survive. By the late 1990s, newer youth-oriented labels had taken over with fresh styles that quickly made Bugle Boy seem outdated. Sales began to fall, and after years of struggling to keep up with changing trends, the company closed its stores in 2001.

8

Howard Johnson’s restaurants

During the 1960s and 1970s, a stop at Howard Johnson's was part of the classic American road-trip experience for many families, and that was no accident.

Founded in 1925 in Quincy, Massachusetts, the famous orange-roofed chain reached its peak when America’s expanding highways and booming car culture made roadside travel more popular than ever. But by the late 1970s and early 1980s, the growing popularity of fast-food chains like McDonald's began changing the way Americans ate on the road. Drivers increasingly wanted meals that were faster, cheaper, and more standardized, while interstate highways also redirected traffic away from many older roadside locations. Unlike some other brands on this list, Howard Johnson’s faded away slowly over the decades. The last restaurant finally closed in 2022.

9

Burger Chef

In 1958, a name emerged as one of the pioneers of America’s growing fast-food industry: Burger Chef. By the late 1960s, the chain had more than 1,000 locations across the country and had become one of McDonald's’s biggest competitors.

Long before Happy Meals became famous, Burger Chef helped popularize the idea of marketing meals directly to children with toys and themed publicity. But during the fast-food wars of the 1970s, competition became fiercer than ever. While McDonald’s and Burger King expanded by leaps and bounds, Burger Chef struggled with financial problems and changing consumer tastes. In 1982, the company was sold to Hardee's, which gradually converted most Burger Chef locations into Hardee’s restaurants.

10

Sports Authority

Throughout the 1990s and 2000s, many Americans looking for running shoes, gym shorts, and sports gear headed straight to Sports Authority.

Known for its huge stores packed with athletic apparel, exercise equipment, bicycles, camping gear, and team sports products, Sports Authority became the ideal shopping destination for families and athletes across the US. But as online shopping rapidly changed retail in the 2000s, the company struggled to adapt. Heavy debt from expansion efforts and a slow shift to e-commerce eventually caught up with the chain. Sports Authority declared bankruptcy in 2016 and closed all remaining stores later that year.

1

Peanuts

Image: ZENG YILI

We’ll start with what some describe as "arguably the longest story ever told by one human being." When Charles Schulz started Peanuts in 1950, he wasn’t aware that he would single-handedly produce a plethora of amazing stories until his death in 2000. The original Peanuts run, which introduced iconic characters like Charlie Brown, Snoopy, and Linus, appeared in over 2,600 newspapers and has been translated into 21 languages.

2

Marmaduke

Image: Oliver Bichard

As any Great Dane owner can tell you, these massive dogs can sometimes be a handful. However, if the comic strip Marmaduke has taught us anything, it’s that no matter how messy their lovable dog is, the Winslow family will always care for their Great Dane, the titular Marmaduke. This comic strip was created in 1954 by cartoonist Brad Anderson, who continued to make Marmaduke comics for 61 years until his death in 2015.

3

Krazy Kat

Image: Shelby Murphy Figueroa

While perhaps not as well-known as other comic strips in this article, George Herriman’s Krazy Kat (also known as Krazy and Ignatz ) is considered by many critics to be one of the most influential comic strips in history. At first glance, Krazy Kat , which ran from 1913 to 1944, appears to be a simple gag-a-day comic depicting an anthropomorphic cat and his mouse rival. However, Herriman’s impressive artwork and groundbreaking creativity have led critics to regard Krazy Kat as one of the most significant pieces of American art .

4

Garfield

Image: Jason Yuen

Garfield is a strong contender for the title of "world’s most famous cartoon cat." True, he is competing with heavy hitters like Tom from Tom and Jerry or Felix the Cat, but this Monday-hating, lasagna-loving orange cat is truly a force to be reckoned with. Created by Jim Davis in 1976, Garfield was first introduced in a comic strip named Jon after the cat’s owner. However, Garfield quickly took the spotlight, and the comic strip was renamed Garfield in 1977. From that point onward, Garfield became an international icon, earning the Guinness World Record for being the world's most widely syndicated comic strip.

5

Calvin and Hobbes

Image: cogdogblog, CC BY 2.0

Can you remember the stuffed animal you would carry everywhere as a child, going on imaginary adventures all across your backyard? Well, for many of us, Calvin and Hobbes perfectly encapsulates those beloved memories. Created by Bill Watterson in 1985, this comic strip depicts the adventures of a young boy named Calvin and his best friend Hobbes, a whimsical and friendly tiger. What’s most moving about this comic strip is that both Calvin and the readers see Hobbes not as a stuffed animal, but as the best friend a young boy could have.

6

The Far Side

Image: Luis Cortés

Up until this point, we’ve been focusing on multi-paneled comic strips, which have several panels at their disposal to tell a compelling story. However, The Far Side has the remarkable distinction of making us laugh heartily with just a single panel. Written and drawn by Gary Larson, this comic strip combines surreal humor with unexpected punchlines , often depicting social situations or the author’s unique view of the world.

7

Dilbert

Image: The Conmunity - Pop Culture Geek from Los Angeles, CA, USA, CC BY 2.0

The break rooms of offices across America are filled with newspapers, which tired employees read during their breaks before returning to work. In that sense, artist Scott Adams perfectly chose office humor as the ideal backdrop for his comic strip, Dilbert . First published in 1989, the strip tells the story of the titular Dilbert, a white-collar engineer trying to navigate the hilarious madness of working in an office.

8

The Family Circus

Image: William Fitzgibbon

At times, the chaos of living with a big family might seem not too dissimilar to the frenzy and excitement of a circus. This seems to be the premise behind the beloved comic strip The Family Circus , created by cartoonist Bil Keane and continued by his son Jeff after Bil’s death. This comic strip revolves around an unnamed family and the many adventures that their three small children and modern life bring to them.

9

Popeye

Image: Jonathan MONCK-MASON

Years before becoming the world’s most famous sailor, Popeye debuted in 1929 as a character in a comic strip called Thimble Theatre . Interestingly, he first appeared when the series was already in its tenth year, but he quickly became its most famous character, eventually overshadowing the original cast and becoming the protagonist. In due time, the strip was renamed Thimble Theatre Starring Popeye before being simply shortened to Popeye in the 1930s.

10

Little Nemo in Slumberland

Image: Hayffield L

We’ll end with the oldest comic strip in this article, which many believe to be the father of all American comic strips. In 1905, American cartoonist Winsor McCay first published Little Nemo in Slumberland . The comic revolved around the titular Nemo, a young boy who often found himself embarking on wonderful adventures in the dream world. McCay’s remarkable artistry and surreal imagery influenced generations of cartoonists and visual artists throughout history.