In January 2000, close to the peak of the dot-com bubble, Cramer recommended investing in technology stocks and suggested a repeat of the stock performance of 1999.[40]

In February 2000, the year in which Cramer claimed to have produced a 36% return, Cramer claimed that there were only 10 stocks he wanted to own and he was buying them every day. These stocks were 724 Solutions, Ariba, Digital Island, Exodus Communications, InfoSpace, Inktomi, Mercury Interactive, Sonera, VeriSign, and Veritas Software. He also dismissed the investing strategy of Benjamin Graham and David Dodd and claimed that price–earnings ratios did not matter.[41] All 10 of these stock picks fell in value significantly during 2000 as the dot-com bubble burst, making the 36% reported return during that year questionable.

On October 6, 2008, on Today, when the S&P 500 Index was valued at 1,056, Cramer suggested to investors, "Whatever money you need for the next five years, please take it out of the stock market." [42][43] Five years later on October 6, 2013 the S&P 500 Index was valued at 1,678 an increase of 58.7%.

Cramer recommended investing in Bear Stearns, Merrill Lynch, Morgan Stanley, and Lehman Brothers before the stocks fell in value significantly.[44] On August 8, 2008, before the climax of the financial crisis of 2007-2008, Cramer recommended investing in bank stocks.[45]

An August 20, 2007 article in The Wall Street Journal stated that "his picks haven't beaten the market. Over the past two years, viewers holding Cramer's stocks would be up 12% while the Dow rose 22% and the S&P 500 16%."[46]

A February 9, 2009 article in The Wall Street Journal noted that betting against Cramer's Buy recommendations using short term options could yield 25% in a month.[47]