A Look Back at Conan O'Brien's Most Memorable Travel Moments

4:51 PM 4/17/2019

by Lexy Perez

Whether starring in a K-pop music video or taking a rum tour in Cuba, the late-night host embarks on a myriad of adventures in 'Conan Without Borders.'

Conan in Cuba Still - H 2015
Courtesy of Turner

Conan in Cuba Still - H 2015

Conan O’Brien is breaking out his passport once again for a new installment in Conan Without Borders. 

The TBS show first began to televise the late-night host’s international travels in 2015 with a trip to Cuba — the first by a late-night host since 1959. O’Brien then created his own mini-franchise Conan Without Borders, where he traveled to a myriad of locations including Cuba, Israel, Haiti, Korea, Mexico, Japan and more. 

For his new adventure, O'Brien will embark on a trip to Sydney, Australia, where he learns how to make "mates" with "Australian slang." 

During an appearance on CBS' The Late Show With Stephen Colbert in 2017, O’Brien expressed how the series has helped him fulfill his “greatest joy," which is "trying to make people laugh that don’t even speak English, don’t know who I am. I love going to these other countries. … It’s a little bit of sort of diplomacy through comedy. I like to show that Americans are curious, we’re humbled. We’re okay to look ridiculous. It’s okay if you laugh at us." 

Amid the premiere of the late-night host traveling down under Wednesday night, The Hollywood Reporter takes a look back at some of the host's most memorable moments from his international travels. 

  • Conan Raises Money for Trump's Border Wall in Mexico

    During O'Brien's trip to Mexico in 2017, the late-night host asked citizens to donate money for the wall President Donald Trump has insisted their country would pay for.

    While walking down the streets of Mexico, O'Brien approached various people to ask them for their donations to a wall piggy bank — only to receive rejections. "If you donate 500 pesos, you get your name on a brick in the wall and you have to act now because there’s only going to be 800 million of these," O'Brien told one citizen, while also offering prizes such as an "I paid for the wall" tote bag and a portrait of Trump that says "Moochas Gracias," spelled to reflect "how he spells it." Another citizen said he wouldn't pay for the wall but would pay with his middle finger. 

  • Conan, People of Haiti Roast Trump

    After President Donald Trump described several foreign nations, including Haiti, as "shithole countries," O'Brien decided to embark on a trip to Haiti to "explore and make some new friends."

    Though O'Brien had difficulty being welcomed by the people of Haiti because he's American — "Make sure Trump knows that you guys are the ones that bullied us and have caused us to be in the state that we are in," one citizen told him — O'Brien attempted to make amends by reciting a speech in the Haitian Creole language.

    "I will be here for several days but if America doesn’t get a new president soon, I may want to stay forever," O'Brien said as the group of people laughed and welcomed him. O'Brien then helped another person get his message to Trump by placing a Fox and Friends border around the camera screen. 

  • Conan Visits a Nude Beach in Germany

    Things got quite heated and scandalous when O'Brien took a trip to Berlin in 2016. Traveling alongside YouTube personality and Pitch Perfect 2 star Flula Borg, O'Brien shared his first experience visiting a nude beach.

    "We're looking right into that man's ass and —," he begins to say, before Borg asked him, "Have you ever seen a man's anus before?"

    After O'Brien said he had, Borg quipped, "Well there's another one." During their visit, Borg and O'Brien also shared schnitzels with the locals, which Borg carried in his fanny pack. 

  • Conan Rents a Fake Family in Japan

    When visiting Japan last year, O'Brien decided to rent a fake family after learning about the service from stories about Japan's crisis of loneliness. While choosing his fake family, he quipped about not having anyone in the "family" older than the 55-year-old comedian. "I'm from Los Angeles and a man my age is required by law to marry a woman who's 25," he said.

    Despite being able to have a fake 35-year-old son, O'Brien said that he feared his fake 48-year-old wife would run off with him and settled for a younger fake daughter. When the late-night host finally met his new fake family, O'Brien laid out some ground rules, such as the family had to laugh at all his jokes and that his father must apologize to him about an incident with creamed corn that occurred in the 1970s. The family ended up laughing every time he opened his mouth. Later, O'Brien and his fake family spend time in Tokyo, wearing masks while on a walk in the park and buying ice cream.

  • Conan Goes on a Rum Tour in Cuba

    After former President Barack Obama's restored diplomatic ties with the nation, O'Brien became the first American late-night host to film in the country since the U.S. embargo began in 1962. Though monumental, the trip marked some comical moments for O'Brien including embarking on a rum tour at the Havana Club Rum Museum. Throughout his Cuba visit, the late-night host learned about the history of rum and drank various samples.

    "This is getting darker...I meant my vision," O'Brien said at one point, as he continued drinking shots. "I'm getting a little bit of the oak of the barrel and urine in my pants," he also quipped. After trying the samples, O'Brien burst into sobs, laid on top of the bar and broke out into song. "Can I stay here until the rum comes to the United States?" he asked the very patient tour guide. 

  • Conan Visits Gal Godot in Israel

    O'Brien took a trip to Israel in 2017, but shared that the only reason he went there was to pay a special visit to Wonder Woman herself. "The entire reason I came to Israel is behind this door," he said to the camera before Gadot appeared.

    Although he couldn't contain his excitement to see the star, Gadot didn't seem as enthused. "Wish you would've told me earlier that you were coming," the actress said as she blocked O'Brien from entering. After he suggested the pair go to the movies or even "ballooning," Gadot seemed disinterested. "I ... I have ... Some people actually just came over and I have plans," she told him. Refusing to give up the chance to hang out with her, O'Brien offered to make her pancakes, which made Gadot laugh. "I just had breakfast," she said, to which the host replied, "That's awkward."

    "Okay, so, I'll see you in L.A." Gadot told O'Brien as she proceeded to close and lock her door. 

  • Conan Stars in K-Pop Video

    O'Brien embarked on a journey to South Korea with The Walking Dead's Steven Yeun joining him along the way. In Conan in Korea, which aired in 2016, the host joined Korean pop star J.Y. Park, The Wonder Girls and TWICE for a music video.

    "I didn't want to leave before making my mark on one of Korea's biggest exports," O'Brien said of living one of his goals for the trip. During the colorful video, Yeun learned how to do O'Brien's "string dance" and they transformed into K-pop stars for the song "Fire." 

  • Conan Meets With A Dominatrix in Germany

    Things got dark during O'Brien's trip to Germany, where he met with a dominatrix at an S&M shop. Prior to beginning, the dominatrix asked whether O'Brien had any "hard limits" to which he explained that he was married. "So no marks," she said, with O'Brien expressing how confused he was with what he was about to do.

    "My fear is for you. You may want to retire after you deal with the white anaconda," O'Brien quipped. The host was later subjected to nipple clamps, a spanking session and donned a rubber mask with the visage of a basset hound.