The Greatest Wall Street Comics of All Time

A reader shared a decades-long collection of Wall Street comics with a financial writer, who selected favorites highlighting 1990s tech stocks and Alan Greenspan, the dot-com bubble's brutal aftermath, and the negativity bias in financial media. The collection includes timeless cartoons on market prediction difficulty and bear market humor.

One of my favorite parts about writing over the years is the regular feedback I get from readers. People send me questions, ideas, charts, movie recommendations, books, old magazines and the occasional grammar/spell check.1 A reader recently shared with me that he’s been collecting Wall Street comics for a few decades. He wanted to send me the entire collection, clipped straight from newspapers and financial publications over the years. I’m a sucker for a good finance comic so I was happy to sift through the whole pile and pick out some of my favorites to share. The 1990s comics had two main focal points — tech stocks and Alan Greenspan. I know there are a lot of comparisons right now between AI and the dot-com bubble the 1990s feel like they were in a different stratosphere: When talking about my book a number of people asked me if we could ever see another Great Depression-like calamity https://awealthofcommonsense.com/2025/11/why-we-cant-have-another-1929/ in the stock market, which was down more than 80%. You don’t have to go back that far to see this level of pain in tech stocks. The aftermath of the dot-com bubble was brutal. The Nasdaq Composite was down nearly 80%. The Nasdaq 100 crashed more than 82%. That’s a Great Depression-like crash in tech stocks not all that long ago. It was painful: When the Nasdaq dropped almost 40% in 2000, the Down was down just 6%. In 2001, the Nasdaq dropped more than 20% while the Dow fell 7%. Investors did have a place to hide out in the more boring dividend-paying blue chips: Alan Greenspan made his now famous irrational exuberance speech https://awealthofcommonsense.com/2025/08/is-this-1996-or-1999/ in 1996. The dot-com bubble was just getting warmed up at that point. Greenspan was a larger-than-life figure in the markets back then. Here’s a good one on the bubble times: And another one: Greenspan was a financial celebrity of sorts back then. Investors hung on his every word: They even covered Greenspan on the B.C. comic strip: This is one of my all-time favorites about the negativity bias in the financial media: This one is similar: That one came out in 2008 but could easily be used today. There are not many bull market cartoons. There are a lot of good bear market comics. This one is funny because it’s true Here’s another Nasdaq one: Also true. This is a good soft landing crossover with a bear market: There were also a series of comics about how hard it is to predict the markets: This one had to come from the likes of Barron’s: Markets can twist your brain into a pretzel at times. This one sounds like something I would say: I’m glad this one was in the collection because it’s the greatest Wall Street comic of all-time: It’s perfect. As the kids like to say — no notes. Further Reading: “The market is rolling simply because it’s rolling” https://awealthofcommonsense.com/2018/07/the-market-is-rolling-simply-because-its-rolling/ 1I surprised how much of this stuff still gets by the AI grammar police.