Guitarist/vocalist Sean McCarthy and his younger brother Dan, who played the drums, grew up in Boston, MA. In 1997, Sean, along with bassist and friend Tina Helms, parted ways with the drummer from their band, the Television Set, but luckily enough, Dan's group, Dagobah, was also reaching its end. Sean and Helms had already booked some studio time for the Television Set, so they recruited Dan to play the drums. After cutting two songs, they realized that this new three-piece lineup had a definite chemistry. They decided to continue playing together, dubbing themselves the Swimmer, and recorded a six-song demo that wasn't released to the public. However, it contained tracks that would appear on the group's split EP with Victory at Sea, as well as their first full-length debut album.
The Swimmer contributed the song "What I Learned From Firecrackers," recorded in the winter of 1997 with producer John Harris, to a Boston compilation titled Halcyon Days that was released in the fall of 1998. Within that next year, the band had gained a name for itself in the Boston area, and it signed a deal with Kimchee Records. As they began recording their first full-length debut, with Kimchee's co-owner Andy Hong producing, the group discovered that Madonna's Maverick imprint was already releasing material from another band named Swimmer. Wanting to avoid any legal trouble, the trio adopted Tina's last name as the band's new moniker in the fall of 1999. Helms didn't have enough material to release its full-length debut album at that time, but Hong wanted to circulate the band's name among the national underground music scene. He asked Boston's Victory at Sea if they would record a split EP with Helms, since Victory at Sea was already going on tour with Helms that summer. Victory at Sea agreed, and Helms used their songs "Plants May Not Have Brains But at Least They Know How to Take Care of Themselves" and "The Smallest World in the World" for the CD, the latter of which would appear on Helms' first full-length. The two bands held a CD release party for the EP on June 29, 2000, at Boston's Middle East nightclub. Two days later, on July 1, the groups departed for their East Coast and Midwest tour. Although the bands were selling the disc on the tour, the CD wasn't officially released in stores until that August.
After the week-long tour ended with Victory at Sea, Helms began playing various one-night gigs with bands like the One AM Radio, the Album Leaf, and the Lapse in their hometown of Boston, as well as various outlying cities in Massachusetts. In that time, Helms managed to hold the CD release party for its full-length debut, The Swimmer. The gathering was held on October 22 at the Middle East with supporting acts Tristeza, the Headset, and the Mercury Program. In February of 2001, Helms began their winter tour of the Midwest and East Coast to support The Swimmer. During this jaunt, they had the privilege of sharing bills with such diverse artists as Arab on Radar, Rose of Sharon, and Tim Kinsellas of Joan of Arc. Helms returned to Boston in late March and continued performing various shows at local venues, as well as writing new material for their sophomore album.
On July 14, 2001, Helms set out for their first full-scale national tour. The outing took the band all the way from the Midwest to the West Coast. They opened the tour for their old friends in the national acts the Album Leaf and Tristeza. As they returned to Boston once again in mid-August, Mister Records approached the group about appearing on the label's 1.5 compilation of various New England bands. Helms contributed the track "Penthouse" for the release.