A Pittsburgh comedian’s AI-assisted track, ‘The Puerto Rico Song,’ turned San Juan—then Caguas—into a looping TikTok anthem, drawing millions of views and celebrity lip-syncs. The viral moment is built on a bigger quest: documenting overlooked cities through s
On April 3, Bill Stiteler’s Instagram and TikTok accounts dropped a video that looked like a travel diary and sounded like a catchphrase. It wasn’t just another clip from San Juan. It was a song—“The Puerto Rico Song”—and the hook was impossible to ignore.
The track. written by Stiteler and crafted with the AI-powered music app Suno. plays over footage of him in Puerto Rico’s capital city and beyond. The video blends bright city shots with everyday moments: taking the subway. stopping at a local grocery store. and spotting a Barack Obama statue. Even the lyrics pull you out of the “pretty vacation” mode and into a bus-station reality.
“It features clips of Stiteler visiting Puerto Rico’s capital city. among others. ” the description of the video makes plain—then the song does the rest. looping lines like: “Immediately was enchanted / The whole plane clapped when we landed / Didn’t wanna do just tourist stuff / So I took the bus to Caguas / It’s a wild place to vacation / Slot machines in the bus station.”.
Within TikTok, the payoff came fast. The video has garnered more than 3.3 million views. And the audience didn’t just watch—they joined in. Fans across entertainment posted their own lip-sync videos to the track. including Modern Family’s Sarah Hyland. country star Luke Combs. and Jennifer Love Hewitt. English Teacher star and creator Brian Jordan Alvarez has made multiple posts featuring the song. and Stiteler credits the actor with kicking off the trend.
The story behind the earworm stretches further than Puerto Rico, though. Stiteler’s viral push didn’t start on an island—it started back in Pittsburgh, with a very different kind of obsession.
After years in New York City as a comedian. he told Yahoo that he took “a little nine-year break to do nothing but drink alcohol.” He got sober in late 2023. moved back to Pittsburgh to live with his dad. and in 2024 bought a Pittsburgh Pirates season pass. He began posting videos of himself going to the team’s home games.
“I remember, like, a day after I made my first video, someone came up to me and was like, ‘Yeah, I saw your video,’ and I was like, ‘What? That’s crazy.’ That happened very fast,” he said.
The account kept growing. Then Stiteler wanted to move past home games—so he followed the Pirates on the road. In 2024, he went to 18 different cities following the team, creating videos along the way. He says the first city for which he created a song was Altoona. Pa. and that’s where he discovered Suno.
“It’s kind of like an auto tuner for lyrics and your voice — you can sing into it, and it can auto tune it into using AI to make music,” he said. “I’m not a musician, I don’t know anything about music, but I’m a comedian, and I can write these funny little songs about all my observations.”
As the concept spread, he says something surprised him. People weren’t drawn to the Pirates simply because of their reputation. What caught attention. he said. were “the adventures of this guy discovering cities you don’t really know about — baseball towns and cities people don’t really think of as traditional destinations.”.
That same logic is threaded through Puerto Rico. The Pirates led him there, even though the team didn’t have a game on the island. The tie is Roberto Clemente. the Pirates icon who played for the team from 1955 to 1972 and grew up in Puerto Rico. Stiteler visited Puerto Rico—specifically Caguas—to see where Clemente had played baseball in his early 20s.
The lyrics even nod to the trip’s off-script choices. Stiteler’s message, through the video and the song, leans toward the places people bypass. “Though people don’t really go to Caguas for vacation. ” he said he found a deeper interest in lesser-explored places. including when traveling internationally. “People don’t want to see pretty beaches on Instagram,” he said. “It’s boring. We’ve hit peak ‘pretty place’ on Instagram and social media, I think.”.
He’s now pushing the travel side of his content in multiple directions. In addition to the songs. he’s leaning into his podcast The Saxcast and his blog the Saxboy Travel Club. which is available on Patreon. And he says the plan is to keep going—especially to places “that not every travel influencer goes to.”.
“I want to find the Pittsburghs of different countries, because there’s a bazillion videos on Paris,” he said. “I want to see the ‘Rust Belt’ of, like, Argentina. Or, what are the industrial towns of France?”
Bill Stiteler The Puerto Rico Song Suno TikTok Instagram San Juan Caguas Pittsburgh Pirates Roberto Clemente Brian Jordan Alvarez viral song