If you’ve been on social media lately, there’s a good chance you’ve seen one of the hundreds of videos posted by those taking the “Puerto Rico Song” challenge. It all started in April 2026, when content creator Bill Stiteler — known online as Saxboy Billy — posted a catchy AI-generated travel song called “First Time in San Juan” on his TikTok and Instagram pages. The Pittsburgh-based comedian wrote the lyrics after being inspired by a trip to Puerto Rico and used the AI music generator Suno to compose the music. The track quickly became a massive earworm, eventually turning into a viral social media challenge. It even became a contender for “Song of the Summer” when users and celebrities started posting their own video lip-syncing, dancing, and recounting vacation highlights to the track. Needless to say, once you hear the song, you’ll never be able to get it out of your head.
