Seth Meyers crushes Castro after 'the most awkward handshake in presidential history'

The event in Cuba this week might be historic but the weird awkwardness has been epic. Tuesday, on "Late Night," Seth Meyers took a closer look at the bizarre press conference with Cuban president Raul Castro that kicked off several days of anti-Obama hate from Republicans.

Obama arrived Saturday in Air Force One, and the incoming flight gave the press an opportunity to capture photos of the plane as it hovered over the old architecture and ancient cars that lined Cuban streets. "It looks like it's traveling back in time. That's Air Force One as it's piloted by Doc Brown," Meyers joked, showing the cockpit.

On the trip, Obama brought with him the and Marriott Hotels, which means that Cuba is close to becoming the new destination for drunk American college kids on spring break. "That's the real Bay of Pigs," Meyers said.

The peak of awkwardness came, however, at the press conference Monday. Obama was eager to answer questions about opening up the country to trade and free markets, and Castro was hoping to gain legitimacy on the international stage. It was never better captured than when the two men shared the most awkward handshake in presidential history. Castro attempted to hold Obama's arm in the air to signify the victory of the two coming together but instead, Obama went with a historic photo-op c*ckblock move letting his arm go limp. "Look at Obama going ragdoll limp," Meyers said. "That might be a puppet's arm. That is the handshake of a photo of a man who does not want a photo taken."

The gun-shy diplomacy makes sense after Obama spent the day taking flack when the delegation was photographed in front of a Che Guevara mural. Many saw it as an implicit endorsement to Urban Outfitters, which could cause an international incident. "Conservatives are upset with the photo, but remember when you visit communist countries you're going to take a picture in front of a communist statue. Even Ronald Reagan was once photographed in Moscow under a bust of Vladamir Lenin and George W. Bush was photographed in Vietnam under a statue of communist leader Ho Chi Minh. Or, as George W. Bush calls Ho Chi Minh, 'the guy from the Billy Joel song. Birth control, Ho Chi Minh, Richard Nixon back again.'"

The awkward handshake wasn't the only uncomfortable moment, because Obama encouraged Castro to take questions from the media. Unfortunately, for Castro, the media asked actual questions that weren't controlled by the government. Questions about political prisoners, for example. Castro denied having any political dissidents in jail the way a kid with chocolate all over his face denies swears he didn't eat the sweets. "What political prisoners? That's exactly what you say when you're holding political prisoners." But if anyone could understand it's Obama – who get's how hard it is to close a prison in Cuba.

There are signs that Obama's visit is having a positive impact on the Cuban people, however. One man told the New York Times he was just grateful the giant pothole got filled in and if he has Obama to thank for it then, "Thanks, Obama!"

Check out the full video below: