Peanuts had a talent for transforming familiar childhood experiences into unique Peanuts punchlines - like the strips that showed the Peanuts kids trying to make some money. Whether they were picking up odd jobs around the neighborhood or making their own kid-approved inventions, the Peanuts kids were quite the enterprising bunch, including good ol' Charlie Brown.

Some of the gang were much more business-savvy than others. For instance, Charlie Brown was never the best salesman or pitcher of his abilities (to no one's surprise). Meanwhile, Lucy saw some success thanks to her psychiatry booth, but that was not the only business she started. Even more of the Peanuts gang have gotten in on the action over the decades, from Snoopy to Peppermint Patty and so many more.

10 "Dogs Don't Give Valentines"

February 13th, 1999

Rerun is a bit of an offbeat kid, much like his siblings - as well as the rest of the Peanuts characters, for that matter. In one strip, Rerun makes hand-drawn valentines not to give to classmates, but instead to try to sell. His business is not all that successful, and he doesn't gain any customers.

One potential customer, who just so happened to be Charlie Brown, thought that the hearts on the valentines looked more like baked potatoes, which is not ideal. Then, Rerun goes by Snoopy's doghouse to try to sell some of his red-heart-covered valentines. Snoopy is not the best customer, however, because apparently dogs do not give valentines, although they will take them. Given how many valentines Snoopy receives yearly, it is wildly convenient that he can accept them.

9 "Willy Loman of the Leaves"

October 28th, 1993

Charlie Brown leaves the house, ready to make some money by raking neighbors' leaves. Putting on his most optimistic view, Charlie Brown is confident that he will be successful with his raking business due to his salesmanship, perseverance, and being well-liked (which does not sound like Charlie Brown at all). Regardless, Charlie Brown's explanation to Sally reminds her of the main character of Arthur Miller's Death of a Salesman, Willy Loman.

Willy Loman's deteriorating mental state leads him to live in a fantasy world where he is popular, influential, and successful, which is at odds with his reality. Much like all of Charlie Brown's businesses, he does not make a single sale despite his hopes and positive thinking. As a result, Sally ends up trying her luck at business, offering to rent people the rake instead. Much like Willy Loman, things do not go great for good old Charlie Brown.

8 "He's Getting Paid?!"

July 28th, 1986

When Peppermint Patty's dad and teacher both think that she is in dire need of a tutor, she meets the smart aleck Maynard, whom Peppermint Patty affectionately calls Captain Tutor. Marcie comes by during a tutoring session, at which point Peppermint Patty learns some important information: Maynard is Marcie's cousin, and more importantly, Maynard is getting paid to be her tutor.

Not thrilled at all with the news that he has been getting paid, Peppermint Patty pushes him and defends her attack by letting him know it is because she thought he was tutoring her out of the goodness of his heart, not for any money. While Maynard is just trying to make a buck, Peppermint Patty wants her tutoring done from the heart, not from the wallet.

7 "Snap Out of It!"

March 27th, 1959

Most normal kids would have a lemonade booth, but not Lucy, of course. Lucy provides counseling services at her psychiatric help booth. When Charlie Brown, Lucy's most frequent customer, describes deep feelings of depression to her, her words of wisdom, expertise, and advice are to "snap out of it!" Content with the services she gave him, she asks for her five-cent payment.

This comic strip marks the first appearance of Lucy's psychiatry booth.

If there is one quality Lucy seems to be low on, it is empathy. Consequently, having a psychiatric help booth is an odd choice for the brash and bossy Lucy. Then again, she is a big proponent of tough love being used for her so-called patients, albeit to no avail. Knowing that time is money, Lucy is not going to give her friends advice for free, necessitating five cents if they ever want her two cents.

6 "Do You Know What You're Doing?"

November 21st, 1985

Charlie Brown takes another shot at entrepreneurship when he tries to sell Christmas wreaths to his neighbor. He does not get off to a great start though, as he starts around Thanksgiving, so no one wants a Christmas wreath yet. This snag did not deter Charlie Brown for long, as he continued to make his rounds. Going door to door selling Christmas wreaths, Charlie Brown is lectured by one of his potential buyers, Franklin.

Upset about Charlie Brown's wreath selling, Franklin lectures his buddy about how he is adding to the commercialization of Christmas with his door-to-door sales attempts. Charlie Brown does not agree, at least not until he can finally sell a wreath. The round-headed kid does have a point there, and luckily for Franklin, Charlie Brown's chance of actually selling a wreath is zero to none.

5 "I Take It Back..."

December 5th, 1990

While many Peanuts fans are familiar with Charlie Brown's crush, the Little Red Haired Girl, he actually had a girlfriend in the '90s comic strips named Peggy Jean. In a Christmas season storyline, Charlie Brown racks his brain on how to get his girlfriend some gloves. At the store, Charlie Brown enlists the help of Snoopy and Lucy to buy Peggy Jean some gloves for Christmas.

The gloves he wants to get her are not cheap, costing $25, which is $25 that Charlie Brown does not have. Lucy offers a solution to Charlie Brown's money woes: sell Snoopy. She then rethinks her suggestion, since she realizes that Snoopy would probably only fetch fifty cents from any potential buyer. Lucy and Snoopy have a love-hate relationship, with them always getting on each other's nerves, as this strip suggests.

4 "They Belong to the Trees"

November 16th, 1976

Trying to make money for Christmas, Charlie Brown tries to do odd jobs for money, like many kids the world over. Offering to rake leaves for Franklin's dad, Franklin turns Charlie Brown away because the leaves are not his dad's but rather the trees'. Walking past the tree responsible for all the leaves on the ground, Charlie Brown draws a line in the sand, letting the tree know that he has no intention of asking it if he can rake the leaves.

This comic strip was the only interaction that Franklin and Charlie Brown had in the 1970s.

While Charlie Brown may struggle to defend himself against the rude words or harshness of his peers, he apparently is not willing to take any guff from the plants of his neighborhood. It is yet another "no" for Charlie Brown and his odd jobs business, in line with the character's perennial rejection.

3 "That Was the Ol' Schmuckle Ball"

June 25th, 1980

Inventing her own kind of pitch, the schmuckle ball, Lucy teaches it to Charlie Brown and advises him to schmush the knuckles around the ball and then throw it as hard as he can. As it turns out, her invention is a huge success and actually helps the Peanuts' baseball team, which is always in desperate need of assistance.

Charlie Brown throws out a pitch that is incredible by any standard and an all-out feat of amazement considering that it's Charlie Brown, so he explains that it was really Lucy's invented pitch. Lucy sees the results of her stellar invention and demands royalties every time the pitch works. Knowing her worth, Lucy will make sure she is compensated for her work. Lucy has tried numerous business strategies, but the schmuckle ball seems to be the most promising.

2 "I Think We Need Better Packaging"

December 17th, 1982

Going into business with her big brother to make some money during the Christmas season, Sally s Charlie Brown in his Christmas wreath-selling venture. Unsurprisingly, they are not met with many sales. In fact, they do not make any sales at all. With no success yet in their Christmas wreath business, Sally thinks that their wreaths need packaging that shows off their product in a more appealing way.

Sally's grand packaging idea turns out to be just sticking the wreath on Snoopy's nose for display. The nose turns out to be distracting as Sally accidentally says she is selling a nice Christmas nose instead of a nice Christmas wreath, not helping in garnering any sales. Snoopy does not appreciate being used as a prop either, eventually leaving Sally high and dry with the wreath still on his nose.

1 "Goop 5 Cents"

May 28th, 1968

​​​​​​​As Snoopy walks past Lucy's goop business stand, she attempts to be a persuasive salesperson and tries to convince him to try some, as well as offering to let him pay by credit card if he does not have the money on him. Snoopy takes a bite of the goop and is instantly queasy, obviously not pleased with Lucy's product. Not one to take constructive criticism, she yells after him that he wouldn't know good goop if he tasted it.

Interestingly enough, before Snoopy, Charlie Brown had tried some of Lucy's goop and had a better opinion of it than Snoopy. That said, he did not think it was great either, thinking it was just okay, but he was placated by the fact that there is nowhere else to get goop for just five cents. One is left to wonder what goop actually is after this Peanuts strip.