Bottle Boys started in late 2017 when Jon, Cole, and Jake T. got together to make some noise at Frogwood Manor. This is beleived to have occured in September of that year, but some Bottle Boys scholars argue for December of that year. Using some recorded samples from the show SpongeBob SquarePants along with ambient guitar and synthesizer, this recording session resulted in the very first Bottle Boys release: SquarePants Dose Drone Vol. 1, consisting of four, lengthy untitled tracks. Bottle Boys ventured into lyric-based music with elements of freak folk and were profilic with their song-writing in the following years. Though much of their catalog from the late 2010s remains unreleased, a very lo-fi recording of a live performance at Coffee Coffee in Salem, N.H. on August 23, 2018 was released on Bandcamp in 2023.

During the initial Bottle Boys years, Jon and Cole continued to write music together. They would share recordings in a Google Drive folder called Northern Mountain Saddle Bellies, which eventually became the name of their duo project when a few of their songs were released by magmacrunch media in early 2023. Around this time, Cole and Jon recorded their classic tune These Toads at the old Slaski House down the street from Frogwood Manor. In the summer of 2023, Cole and Jake T. recorded a EP under the Bottle Boys name called The Legend of the Backpack Man. Later that year, NMSB wrote and recorded a song called Tollbooth Landy. However, as of spring 2026, this track is still in production for a guitar solo.

The NMSB project expanded to include Ben N. aroumd the turn of 2023 to 2024. As a trio, they released two cover songs in 2024 that were released on Youtube: Lonesome Town by Ricky Nelson and I don't want to live on the moon by Erine from Sesame Street.