"This is a really Dickensian, 'Tale-of-Two-Cities'-style market," the "Mad Money" host said. "It is at once the best of times if you own the banks and the techs or the industrials, and it's the worst of times if you own the drug stocks, the consumer packaged goods plays or anything retail. This dichotomy plays out every single day."
Cramer pointed to Citi Research's twin downgrades of Macy's and J.C. Penney's stocks to "sell" from neutral ratings. Citi's analysts cited the department store chains' lack of strategic initiatives to differentiate themselves from competing retailers.
"Citi says that J.C. Penney is withering, that they've cut expenses to the bone — no, through the bone — [and] they need to add the expenses back," Cramer said. "The merchandise is not distinguished, the home goods have lower gross margins. There seems to be no way out."
As for Macy's, Citi said the retailer needs to be able to cut its 8 percent dividend yield.
"If that's the case, then there's not much reason to own the thing," Cramer said. "I thought the report was too downbeat and that CEO Jeff Gennette deserves a little more of a honeymoon than this. I mean, the guy's only been at the helm for about eight months. But this downgrade? It made me feel like time is running out."
Almost eight months after Snap Inc.'s initial public offering, Cramer wondered if the beleaguered social media company could be getting its groove back.
After coming public at $17 a share in March, Snap's stock hit its peak of $29.44 on its second day of trading before starting a long journey down. The stock bottomed in mid-August at $11.28.
"But now, the situation's starting to get different," Cramer said. "Almost all the hype surrounding Snap has dissipated, the enthusiasm surrounding the stock has completely vanished, and even though the share price has been steadily working its way higher since the August lows, the recent strength's gotten very little attention."
Shares of Snap have, indeed, rallied over 30 percent since its all-time lows in August. As the stock stabilizes ahead of Snap's third-quarter earnings report on Nov. 7, Cramer asked the question many investors want answered: has Snap become a worthy investment?
Cramer has noticed a lot of action in the stock market recently that, in theory, shouldn't be happening.
"This is a market that seems to have suspended nearly all of the ordinary rules that we go by. Things that aren't supposed to happen have been happening at a faster pace than at any time I can recall," he said. "So many stocks are behaving incorrectly, at least compared to the long-held hedge fund playbook."
With interest rates heading higher and several rate hikes by the Federal Reserve expected for 2018, Cramer argued that the worst stock group in the market should be housing.
When short-term interest rates rise, borrowing costs for loans become more expensive, so people trying to secure new mortgages could fall under financial pressure. That could deter others from taking out loans for new houses or cars.
But when Cramer looked at the charts, homebuilding stocks were some of the best performers when it came to the new-high list. And that wasn't the only oddity this bull market is proffering.
As sports retailers like Under Armour fall under pressure from the brick-and-mortar slowdown, Columbia Sportswear's President and CEO Tim Boyle told CNBC that his company's key to success has come from standing out.
"Nobody needs another brand of footwear or apparel. Regardless of how impactful our products are, it's about being different and it's about differentiating yourselves from others," Boyle told Cramer on Monday.
Boyle cited his company's ad campaigns featuring his mother, rap artist Macklemore, Hollywood brothers Zac and Dylan Efron and Disney's Star Wars franchise as examples of creative collaborations, adding that Columbia could be doing even more to spread its message.
"Our marketing spend is only around 5 percent of sales. Some of our competitors spend up to 12. We don't think we need to spend that much, but we need to find more capital to spend on marketing and, frankly, we need to be more profitable," the CEO said.
"We have legacy activities which are not moving the business forward," he continued. "We need to uncover those, allow our employees to really talk about those areas of the business which are not helping and may be holding us back, and allow for the business to grow, become more profitable and throw off more money for marketing. So we want to tell our story better."
With Amazon encroaching on traditional retailers' turfs, companies like Tractor Supply, the country's largest rural lifestyle retailer, have to enhance their digital wares to keep up.
Tractor Supply CEO Greg Sandfort told CNBC on Monday that, in addition to the chain's practice of hiring local customers who know their communities, Tractor Supply's digital initiatives will help the retailer keep pace.
"I think our focus on the digital component of our business is what's important," Sandfort told Cramer. "Buy online, pick up in-store has really been the key. We turned that on about a year ago. It's doing quite well."
Tractor Supply has also introduced mobile point-of-sale systems in its stores, letting customers check out anywhere inside (or outside) the stores, the CEO said. In addition, the retailer has enacted Neighbors Club, an online benefits program, and a system that allows stores to offer larger product inventories than they can physically hold by selling items online.
In Cramer's lightning round, he zipped through his take on some callers' favorite stocks:
Regeneron: "[CEO] Len Schleifer's doing everything he can. I mean, this company is one of the great biotech companies of all time. The problem is that everybody has decided that the drug business is not the business that we're used to and there's a lot of competition, a lot of companies going at it. And that includes Regeneron versus Amgen. I think you're fine and I think Len's doing great, but I'm not crazy about the industry."
Acacia Communications: "It's a very competitive business now. They had these Chinese contracts that didn't work out and that really set the thing going down, and since then I've really kind of had to walk away from it, frankly. The Chinese contracts spooked me."