One of the original artists on the Twin/Tone Records label, he performs one of the most popular shows in the Twin Cities, an annual tribute to John Lennon held at First Avenue.

[4] Ira Robbins of Trouser Press called him "a talented songwriter with a great sense of humor, an adequate if colorless voice and connections with every other local Minneapolis musician (except maybe Prince), many of whom played on his first album.

Its B-side, "Land of the Free", was played at Solidarity rallies as the Polish trade union protested martial law.

[9] In a retrospective review of Curtiss' Twin/Tone albums, Trouser Press' Robbins called Courtesy "energetic rockers in a niche between Marshall Crenshaw, Bruce Springsteen and George Thorogood, but much rawer and less predictable."

Noting that A Scarlet Letter was made after a particularly bad year in Curtiss' personal life, Robbins said that the album was "easily his best record", a set of resonant roots rock" whose "nakedly emotional missives ... get soulful treatment from Almsted’s impassioned voice, which has really come to resemble (Willy) DeVille’s."

Curtiss describes his collages as dreamscapes where iconic figures—or other images that embody a mythic quality—are placed in iconoclastic situations or surroundings.

He often uses political and theological images along with depictions of superheroes to represent the constant struggle for justice and to question who or what is truly good.

[5][9] Almsted has been honored with a star on the outside mural of the Minneapolis nightclub First Avenue,[12] recognizing performers that have played sold-out shows or have otherwise demonstrated a major contribution to the culture at the iconic venue.