Hultgren first began recording instrumental guitar drone pieces in 1992 before teaming up with Weber. By the end of 1993, the duo had issued a single, "Watersong," on the musicians' own Blue Flea label. Several self-released cassettes appeared in 1994, including Portal, which was reissued with additional material by Ba Da Bing in 1995. The duo participated in psychedelic group Once Dreamt, whose Drifting EP was also released in 1995. Drawing of Sound appeared on Icon in 1996, and the duo's 1997 release Antarctica was the second volume of Darla's The Bliss Out series. All the while, the pair continued releasing limited EPs and split singles with groups including Füxa and Silver Apples.
In 1998, Windy Carl joined the roster at Kranky Records, releasing the full-length Depths. 1999 saw the duo collaborating with synthesist Greg Gasiorowski and releasing the album Transcendence as the side project Five Way Mirror. A live collaborative album with the Lothars, a split CD with tourmates Landing, and Kranky full-length Consciousness all appeared in 2001. Windy Carl then took a hiatus while the couple continued to run their record store, Stormy Records, in Dearborn, Michigan. They rounded up three CDs' worth of non-album material as Introspection: Singles Rarities 1993-2000, issued by Blue Flea in 2002.
The duo returned to their songwriting project in early 2005, first paying tribute to a recently departed dog (Dedications to Flea, a limited-edition release on the Brainwashed label) before pairing the disc with a dreamy, ambitious effort titled The Dream House. Following Weber's solo full-length I Hate People, Windy Carl's fourth Kranky-affiliated effort, Songs for the Broken Hearted, appeared in 2008. During the time leading up to and directly following Songs for the Broken Hearted, the group experienced a surge of new listenership, sparked in part by successful Deerhunter frontman Bradford Cox repeatedly referencing in interviews how influential Windy Carl's early recordings were to him. This piqued the curiosity of new fans and earned the record a broader audience and critical acclaim, with more media coverage than usual for the duo.
They returned in 2012 with We Will Always Be, a full-length of collaborations based on intimate solo recordings by Hultgren, initially gifted to Weber as a Valentine's Day present. Numerous limited releases, singles, and Hultgren's first solo album (2014's Tomorrow) appeared throughout the remainder of the decade. Allegiance and Conviction, their first Kranky release in eight years, arrived in 2020. The duo also issued the triple-CD collection Unreleased Home Recordings 1992-1995 through Blue Flea. ~ Jason Ankeny & Paul Simpson, Rovi