Conan O'Brien admitted the history making segments he recently filmed for his "Conan" TV show almost never happened.

The Los Angeles Times reports O'Brien recently became the first American TV host to tape segments of his show from the island nation of Cuba.

On Wednesday night, he shared with "The Daily Show" host Jon Stewart just how much he truly had to go through to see that mission accomplished.

"We weren't sure we were going to get into the country," O'Brien said. "We didn't make a lot of preparations. ... We were told we had the right papers. We showed up, there is no Internet, so our phones didn't work. ... We walked in, we handed our papers to them. The guy looked at them, our phones are dead, our plane is gone, and the guy just looked at us and said, 'No.'"

But after several episodes of the "Gilmore Girls" dubbed into Spanish later, O'Brien's fortunes changed, and he and his "Team Coco" staffers were granted clearance. Soon after that, he was immediately spotted by Canadian tourists who just as quickly recognized who he was.

The episode O'Brien and his team worked on is slated to air on TBS on March 4, and features the funnyman host visiting a Cuban cigar factory, getting intoxicated at a rum factory and learning to dance the "erotic" rumba.

All and all, the former "Tonight Show" host described his experience as a "sophisticated spring break."

After a nearly 50 year embargo, President Barack Obama recently normalized U.S. relations with Cuba allowing for some trading between the two nations. A second round of diplomatic discussions are scheduled to kick later this month in Washington.

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