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The "Circles" singer, 26, joined Meyers, 48, on Late Night Wednesday for a round of day drinking that culminated in not only a fresh set of ink for the host, but in a Cheers-inspired sing-a-long.
As they always do in the popular segment, things started relatively low-key for the pair, who began by chugging a beer at the New York City bar The Waylon.
After a trivia quiz game resulted in several rounds of shots, they then tackled a series of mixed drinks crafted by Meyers and inspired by the many tattoos of Malone, who released his fourth album Twelve Carat Toothache earlier this month.
Among the er, interesting concoctions? The "Tired No More," which included coffee, Red Bull, Four Loko and Pixy Stix, and the "Stay Away Gibson," made of gin, dry vermouth, brine and pickled onions.
Lloyd Bishop/NBC Seth Meyers and Post Malone
"This smells crazy," Malone said of the second drink. "This might be one of the most vile things I've ever tasted. And I've tasted a lot of crazy … stuff."
After cleansing their palates with Malone's rosé wine, Maison No. 9, the two played a game called Post It, in which they had each other guess celebrities like Bob Dylan, Tom Cruise and Stephen King.
Then it was tattoo time, during which Malone took a Sharpie to Meyers' face to draw several tattoos he'd requested, including the Pittsburgh Steelers logo, the Flash logo and his Italian Greyhound Frisbee.
"I'm enjoying this," Meyers said as Malone worked his magic.
"It's nice, it's therapeutic," the Grammy nominee agreed. "We're gonna give you a nice forehead banger… I'm not brave enough to do this."
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Despite Malone's experience with tattoos, it clearly didn't translate into artistic ability, as Meyers had a difficult time making out which drawings were supposed to be what — except, of course, the word "Hi."
With the tattoos done, Meyers wrapped things up by moving to the piano, where the duo did their own (drunken and off-key) version of the Cheers theme song.
"I want to say something. So Cheers is like, the greatest show that ever took place in a bar," Meyers explained. "And the guy who owned the bar was named Sam Malone, and your name is Post Malone, and you're an incredible musician and I would like us to move over to this piano right now and sing the theme song to the hit television show Cheers."
The segment is set to air on NBC's Late Night with Seth Meyers Wednesday night in an episode that will also feature Adam Sandler and James Patterson.