TheStreet's Jim Cramer and former late night talk show host Jay Leno agree: Whether it's American's negative view of politics, corporate success, or the financial markets -- pessimism isn't a good thing. 

"I'm just urging people to be less pessimistic, within the context of being skeptical," Cramer, TheStreet's founder and manager of the Action Alerts PLUS portfolio said in an interview. "It's OK to be skeptical, but pessimism has not made you a lot of money in this market and that's really important, that's a really important concept."

In an interview with Leno on CNBC's Squawk on the Street Tuesday, Cramer and his co-host Carl Quintanilla, questioned why Americans seem cynical about American companies like electric vehicle maker Tesla (TSLA - Get Report) and iPhone manufacturer Apple (AAPL - Get Report) , who seem to be creating interesting products and changing how we live our daily lives. 

"I don't quite understand why we don't celebrate entrepreneurship and success more in this country," Leno said. "I'm very optimistic. I'm one of those people who believe that engineers will save the world."

Leno, who has a love for cars and owns a Tesla Model S P90D, will be hosting a show on CNBC called "Jay's Leno's Garage." He said he is impressed with innovations. For example, "Los Angeles has millions of more cars than it did in 1972 with a tenth of the smog," but he understands improvements are still needed for better car emissions.

"We're becoming like the British now. We like noble failures more than we reward success," he said, comparing the Tesla maker to other American inventors. "I think Elon Musk is the Thomas Edison or the Henry Ford." 

While most people believe cars depreciate as soon as they are driven off the lot, Leno highlighted that cars that are technically interesting, fun to drive, and are no longer in production will go up in value like certain models of Ferrari or McLaren. 

Leno hosted "The Tonight Show With Jay Leno" until 2014, during the time when presidents Bill Clinton and George W. Bush were put through scrutiny as they ran for office. He and Cramer agree that politics in the 2016 presidential election have become too negative.

"It's so ugly now," Leno said. "I'm kind of glad I'm not on, because I feel like every time I do a joke about Trump maybe I'm somehow promoting him." 

Cramer said Leno's optimism "dove tailed" with his view of the financial markets, which is not that the markets "won't go down," but that investors should stay positive. 

Cramer highlighted examples of Union Pacific Railroad (UNP - Get Report) , which was trading around $83 and looked like it may go as low as $75, but almost reached $89 Tuesday, as well as other companies investors predicted would "go under" like Chesapeake Energy (CHK - Get Report) , Southwestern Energy  (SWN - Get Report)  and Cliffs Natural Resources (CLF - Get Report) . Each have seen some positives from their lowest lows. 

"Maybe Jay was right about some things," Cramer said. "He came with a very optimistic, but also sad view. He urges us to be a little more optimistic." Investors should pay attention.

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